Recession Talk, Pivots, and Freelancing in 2022

It’s a weird time…especially now that the big “R” word is floating around. (Recession, that is.)

Lately, I’m feeling the same way I did about two years ago when the world was shut down, and I was debating whether or not I should get a PPP loan.

I find myself wondering:

• Will content budgets get slashed, leaving my services unneeded?

• Will companies move more writing work in-house, cutting freelance budgets?

Uncertainty abounds, and it doesn’t feel great if I’m being totally candid. For the first half of this year, I’ve been inundated with work. But now: I don’t know. Things are definitely quieter. Friends working as in-house marketers have been let go. Some of my biggest clients are reporting missed earnings and layoffs.

I bring this up for a few reasons.

Number one: To make it clear that if you’re in the same boat right now, you’re definitely not alone.

Number two: To advocate for income diversification.

We can’t know what the future holds, but having a few income streams can help offset some of the current “weirdness” when it comes to freelance work (or even full-time work, for that matter. I know in-house folks are feeling this right now too!)

For me, this means continuing to promote my productized service turning podcasts into blog posts over at Content Remix, trying to do a better job of talking about the premium digital resources and consulting offerings I have, and considering offering more live sessions (like the ‘How to write like a journalist’ one I offered earlier this year), and exploring more long-term partnership opportunities.

But it’s also got me thinking about the good ol’ fashioned pivot.

I’ve already done a bit of pivoting in my eight years of self-employment:

• I stopped doing copywriting projects and social media management (and stopped marketing my services through a brand name rather than my own name.)

• I stepped away from the two annual retainer clients I had a few years back.

• I niched down my content writing work to focus solely on clients in the ecommerce software space.

But friends of mine have made even more dramatic pivots, transitioning across industries and roles (and they’re finding great success!)

• Sarah Moret went from working in finance and venture capital to founding Curie, a natural deodorant and body care product line.

• Val Geisler went from working in the theater space to working in-house for a software company.

I posed this question on Twitter, and there were TONS of interesting stories of pivots shared in the replies here.

So, I guess what I’m saying today is: Yes. Things feel up-in-the-air (again.)

And that doesn’t feel great. Nobody likes uncertainty.

BUT! Moments like these also present opportunities to sharpen our skill sets, to find new ways to bring in money, to experiment with new service offerings, to lean into that creative project you’ve been putting on the back burner, or to make a brilliant, dramatic transition into something totally new.

The bottom line is: hang in there.

After all, necessity is the mother of invention, right?

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New: The Book Corner

Welcome to a new segment where I share a review of a book I've recently read and enjoyed (I'll spare you the ones that sucked.)

A bit on my reading preferences, in case you want to know what to expect here: I'm a big fan of fiction, but I also love a good sci-fi thriller from time to time, an insightful memoir, the occasional modern romance/beach reach, and historical fiction.

First up: Three Women by Lisa Taddeo

Lately, I've been reading books where the reader gets to go inside the minds of female narrators and swim in their thoughts, worries, and obsessions.

This one was no exception. It's the story of three different women (identities altered) who share their personal stories of love, loss, and internal thought processing around those events. Definitely a trigger warning for this one, but if you can compartmentalize, the writing is truly brilliant and the stories are a rare glimpse into the narrators' inner dialogues around personality-defining events. I read this in two days and couldn't put it down.

I Changed My Mind About Public Speaking

For many years, I’ve resisted speaking gigs. In fact, I’ve even taken a stance against conferences in the past.

I haven’t raised my hand for opportunities to be on stage and always preferred to stay in the background, working behind the scenes.

I recently read this in Glennon Doyle’s book Untamed, and it rang true for me in a big way:

“I am a sensitive, introverted woman, which means that I love humanity but actual human beings are tricky for me. I love people but not in person. For example, I would die for you but not, like...meet you for coffee. I became a writer so I could stay at home alone in my pajamas, reading and writing about the importance of human connection and community.”

Aside from introversion, the other reason I haven’t thrown my name in the hat for these opportunities is because public speaking made me NERVOUS.

Like: Can’t eat, can’t sleep for days before the thing nervous. I once was so nervous before a speaking gig that my shaky hands spilled steaming hot coffee all over my pants (thank God they were black.) Now my family refers to the nervous version of me as “ol’ coffee pants.” Sigh.

BUT! Last November, I was hired to present a 60-minute session (in person) to a marketing agency in New York. The topic was based around an article I’d written for Vogue Business, and they brought me in to dive deeper into the topic and facilitate a brainstorming session for a small group of their employees and clients.

Needless to say, it felt *very* grown-up and serious. So I went into my default mode and planned everything I could to eliminate stress-inducing anxiety.

• I built out my slides and made notecards of my talking points.

• I picked out the perfect outfit. And coat. And shoes. And accessories.

• I booked at a hotel across the street and arrived the night before the event to eliminate travel friction.

All of this seemed to help, except for the part when I got to the airport and realized I didn’t have my driver’s license on me. I’d left it in a pants pocket back at home, 90+ minutes from the airport.

I was able to fly after waiting for an extra-thorough security check and an overnighted passport (thanks, Dad.) So…yeah. Close to covering all my bases to make things go smoothly, but not quite close enough.

Anyway: I made it there. I was the first speaker the next day, so I walked over early that morning (as in: I was there before the organizer was) and got my slides set up before hiding in the bathroom for a few minutes to collect myself.

A pic from that morning

Ready to go!

When I came back to the meeting room, people were filing in, and I grabbed a cup of hot tea (that I didn’t spill!) and waited up by the front of the room where my slides were.

And guess what?

• I didn’t feel nervous.

• I felt calm.

• My hands didn’t shake.

• My breathing was normal.

• I wasn’t sweating through my clothes.

• I didn’t have a splotchy red rash creeping up my neck.

It was the strangest thing.

I gave my presentation, pausing along the way to answer questions and pursue tangents based on the conversation the topic sparked. People nodded while I was speaking. I felt myself getting more comfortable as I went on, speaking with my hands and my face getting more animated.

I felt…confident. Sparkly. Like I really knew what I was talking about (I did) and that people in attendance were interested in what I had to share (they were.)

I was the expert in the room, and it felt really good. No more Imposter Syndrome. At 33, I finally felt self-assured enough to realize: I can do this. Not only that, but I’m good at it.

So guess what?

I’m changing my stance on public speaking and attending/speaking at conferences.

This is the year I’ve decided to lean into getting on stages and adding my voice to teach what I know. It’s time for me to get over this mental block that speaking is something that’s “just not for me.”

The reality is: It’s not that I don’t like public speaking. I was just scared. I was very much in my head about it. And that limiting belief has held me back for years.

I’ve already got a handful of events lined up for the coming months so far, including the Creator Economy Expo in Phoenix, an eCommerce event for women in LA, and the Retail Innovation Conference in Chicago. (Please let me know if you’ll be at any of these…I’d love to say hello!)

I also want to put it out there: If you hear of a conference looking to add female voices to its speaker lineup (so…most conferences!) where you think I’d be a good fit, please send it my way or pass my name along. I’m doing my booking in a very DIY fashion right now with no formal speaking agent, so it really takes a community effort to spread the word I’m doing this now, you know? I’d super appreciate that.

2020 Year in Review

Welp…2020 did not go how I expected it to.

I know you can relate with that sentiment; we’re all in that boat.

But even with all of the uncertainty, the cancelled plans, and the pivots that happened this year…it was still a good one. I was fortunate in a big way.

This was my seventh year of full-time freelance writing, and somehow it was my best year revenue-wise to date: As of the end of December, my revenue was up 76% over 2019.

I’m breathing a huge sigh of relief and gratitude with that statement, as I vividly remember back in March when I was considering applying for a PPP loan (I opted not to in the end) and feeling super anxious about the future of my client work. 

I had no idea if companies would cut freelance support as they got conservative with budgets or if they’d lean into online content creation with events and in-person marketing off the table.

Thankfully it’s been the latter, and I’ve kept so busy this year that I’ve been getting help with overflow assignments and sending referrals to fellow writers a handful of times each week.

So what else happened in 2020?

Solo writing retreat + socially distant meetups

The first week of January, I took a three-day solo writing retreat up in Galena, Illinois to work on finishing the first draft of a creative writing project I’ve been working on. 

That’s still a work in progress (in need of some major rewrites which will be starting soon), but it felt so good to hole up by the fire in a cozy cabin for a few days with no client work just to focus on writing something *for fun.* 

During warmer weather, I also got to see a few fellow writers via outdoor, socially-distanced meetups.

My local writer friend Courtney Westlake came over up a few times to co-work with me on our back patio, and I got to see Allie Decker for a bit when she was nearby on a solo retreat of her own. It’s always so great to get face time with people who “get” what you do.

New business developments

Launching digital products and productized services

In January I officially launched my first digital writing resources. I’d been putting it off for a long time in fear of coming across as a spammy salesperson, but finally got past that and just, as they say, “shipped it.”

It was a good decision: I’ve sold just under $10,000 in digital products this year, and hope that number will go up in 2021 with a transition on the horizon around these offerings (more on this soon!)

I did a lot of experimenting with different teaching formats, too. I did a handful of live sessions on Crowdcast where I taught various writing lessons. In the second half of the year, I started offering one-page website copy audits as well. Together, these generated another $14,000-ish in revenue.

I continued my coaching work as well, and was excited to have a more diverse mix of both male and female clients this year.

Upon reviewing the increasing demand and surveying past students, I decided to finally increase the cost of the four-week program to $2,200 to better reflect the results and ROI the program generates for participants.

I hadn’t raised the price at all in over three years of offering this service, but looking at the impressive results and feedback from past students, I realized it was time to re-evaluate that.

Newsletter transition and reporting work

In July, I moved my newsletter from Mailchimp over to Convertkit. It’s been a great decision so far, as performance and deliverability have both gone up significantly since making that switch.

I also landed some new and exciting online bylines this year with places like Vogue Business, Protocol, and Modern Retail, as well as in print for Mission Magazine. 

The most interesting piece I wrote for a publication this year was based on a video chat I had with Shep Gordon, the “Supermensch” Hollywood talent manager for Alice Cooper and Blondie (and many others.) I loved what he had to say about taking a service-based approach to networking and was nodding along the whole time.

The end of the road for Creative Class

The other big development: My Creative Class co-teacher Paul Jarvis and I have decided to wind down our efforts around our freelance business course and podcast in early 2021.

Paul and I are both at a point where we’re largely focusing on other things (him on building Fathom Analytics, me on building out more resources for freelance writers), so it seems like the right time for both of us.

We’ll have one more season of the podcast come out (releasing January-March) and one final course launch window in January, but those will be our last.

It’s bittersweet, but I’m looking forward to the next chapter and building out some more robust offerings of my own!

Travels (pre-March)

In January, my husband Brandon and I went to NYC for a few days. We stayed at the PUBLIC Hotel and did lots of walking: We went to The Met, ate at Freeman’s Alley and had drinks at Ray’s Bar, saw a movie at the Roxy Theater, sat in the cozy pit at Sky Ting’s yoga studio in Brooklyn, and so much more. It was cold and snowy for much of the trip, but that’s one city that’s even prettier in the snow.

A few weeks later, I went to Oahu to watch the Billabong Pipeline Masters surfing competition. Hawaii was so beautiful, and it was such a welcome escape to perfect weather coming from the dead of winter in the Midwest. I even got to do an outdoor aerial yoga class one morning!

I turned 31 a few days after getting back from this trip, and that’s when things started closing down due to COVID. We had more trips planned for later in the year (California, Boston, and NYC again), but all of them were cancelled. Once things started closing down in March, we decided to play it safe and haven’t taken any trips since then.

Since we didn’t do much traveling this year, we decided to donate some of those previously-allocated funds to causes we care about, like the Central Illinois Foodbank and several local no-kill animal shelters.

The great outdoors

One of the benefits of not traveling this year is that Brandon and I have been able to spend way more time doing outdoor activities we don’t normally get around to. 

We biked hundreds of miles with my brother on new trails we found in a nearby town, foraged and found lots of tasty morel mushrooms, kayaked, hiked, and took Brooks (our doggo) on lots of walks and Jeep rides. 

I also started stand-up paddleboarding this year, which I love! I even got back into running. All of these physical activities have been a saving grace for my mental health.

Life things

In the fall, I had a friend cut more than 10 inches off my hair (outside, with masks on) so I could try out short hair for the first time since 5th grade. Turns out: I like it! It’s faster, it’s lighter, and I think it makes me look a bit older.

During quarantine I haven’t gone into any sort of salon, so I figured I’d just highlight my own hair with a box kit (like I used to do in high school.) That was a very bad call, as my roots turned orange. 

A cosmetologist internet friend sent me corrective color, but while I waited for that to arrive in the mail, I experimented with some fun colors to cover up my oops (pink was super fun, as was lilac.) The moral of the story is don’t try to bleach your own hair at home, k?

In October, my husband and I bought a new house, which, hilariously, is right across the street from the house I grew up in. Didn’t see that in my future!

The house is still a work in progress as we make some changes before moving in, but we’re hoping to be moved in there this spring. It’ll be so strange to have a new office space after working in the same spot since the start of my freelance career seven years ago.

Favorite reads

I had plenty of time for reading this year, and these were some of my favorites.

The Woman Destroyed by Simone DeBeauvoir: I really enjoyed the first and third stories in this book (the middle one was written in a writing voice I couldn’t really get into.) This was excellent female perspective during my Existentialism philosophy kick this year.

The Midnight Library by Matt Haig: A fast read with a great original story and a positive message. If you’re into the idea of multiverses, this is up your alley.

The Lying Life of Adults by Elena Ferrante: This author is one of my all-time favorites for her ability to tease out characters’ emotions and to put you inside their heads.

The Harvard Psychedelic Club by Don Lattin: I had no idea about the magic mushroom experiments that went on in the 70s at Harvard and the careers of these famous folks that emerged from it. Loved this piece of nonfiction!

French Exit by Patrick DeWitt: Writer Rachel Syme recommended this book as a fun story with larger-than-life characters, and it delivered. A quick, light read.

Goals for the year ahead

I’m hoping that 2021 will be a year where I can branch out a bit more, diversifying my work beyond writing and getting a bit deeper into digital products and consulting. 

My biggest goal: Teach more than 2,000 people how to run a successful freelance writing business. I’ll be doing this through some new resources that are on the way (coming soon!) as well as the resources I already have for sale now.

My long-time writer friend Emma Siemasko are also launching a podcast together that’s aimed at freelance writers. I love chatting with her anytime I can, and with both of our combined years of experience as freelance writers working with clients in the US and internationally, we have a whole lot to talk about and share.

I’ve also got a few virtual speaking gigs lined up for 2021, so while I don’t plan to put a big focus on presenting in the coming year, I will be doing a few of these with sizable audiences. The first one is coming up with SEJ’s eSummit in January.

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Did you do a post like this—or do you have an accomplishment from 2020 you’re really proud of? I wanna hear about it. Tweet me @kaleighf.

This originally appeared in my newsletter, A Cup of Copy. Sign up and get future editions delivered to your inbox.

The Ultimate WFH Product Guide: Clothing, Home Office Improvements, and More

Today, I want to spotlight some of my favorite things that have helped optimize my workday as a freelance writer that works from home. This includes cozy WFH gear, home office improvements, brain fuel, and more.

Why am I sharing this?

Because, let’s face it: The internet is huge and it can be hard to discover new, cool stuff (that someone else can actually vouch for.)

Let’s start with my favorite cozy work-from-home wear.

Cozy WFH Clothing

These are the pieces I find myself reaching for week after week as I work from my home office in comfort. Admittedly, these items are mostly for ladies, as that’s what I buy. So...guys? Maybe put these on your to-gift list for the ladies in your life, k?

First up: Three pairs of pants in my weekly rotation

• Athleta Polartec leggings: These are my go-to winter leggings. They’re nice and thick for days when I want the compression of a legging but need something that’s warm enough to walk the dog in during cold temps. Expensive but worth the investment.

• Prana Buxton jeans: If for some reason I feel the urge to wear jeans, I reach for these. Not only are they nice and stretchy, but they’re made from a cotton blend that makes them feel super soft on the inside. Bonus: They’re straight leg, meaning you have room to wear a base layer under them if needed. (Athleta’s Sculptek denim is comparable, and they are my second go-to for jeans.)

• Feat joggers: I have three pairs of these bad boys (that’s how much I love them.) They fit high-waisted and the buttery material stays wrinkle-free. Bonus: They’re ⅞ length, which means they actually fit a short gal like me lengthwise. (There's a men’s version available, too!)

Next: Cool weather cozies

• Aerie Sherpa pullover: This pullover is sort of like wearing a nice, soft blanket. I’m weird about fabrics, but this passes the test with flying colors. I love how soft and warm it is. Very cozy.

• Herschel sweatpants: These are nice and thick! A great warm option for days when I need to layer up. They run a bit long, so I do have to roll the band over to get them to the right length for me, but not a big deal. (Guy version of these as well!)

• Athleta Pranayama wrap: The fabric of this wrap is so, so soft. It’s mid-weight, has pockets and thumb holes, and looks super put-together without sacrificing comfort.

Versatile pieces: Loungewear to activewear

• Aviator Nation t-shirts: I don’t know how in the world this brand has figured out how to make the perfect unisex vintage-style t-shirt, but they have. They’re crazy soft. Plus: I can wear these during exercise too, which means one less outfit change during the day.

• All Access Center Stage leggings: These are a recent discovery for me, and I love the seamless look. Great fabric, a good band that doesn’t cut me in half, and quality construction. Again, these are expensive, but I’ll wear ‘em for years. Got these from Bandier and I’m in love.

• Aerie thermals: I have at least eight of these in various colors (the henley and plain long-sleeve versions.) Perfect base layer that I can work and exercise in comfortably.

• White Fox tank: This tie-dye crop was in heavy rotation during warmer weather, although it’s a bit chilly for it now. Will bring it back this spring.

Dressed up from the waist up

On the days I need to look semi-professional (for Zoom calls or live training sessions, for example) I usually just put on a nice-looking top or jacket. No one’s going to see my leggings or sweatpants and slippers, so I won’t tell if you don’t. Lately, these three items are my go-tos:

• Boden Celia top: It feels so French! Also love that it has a mock neck because sometimes I get a nervous rash when speaking and this covers it up.

• Liverpool moto jacket: Super chic. So easy to put on over a long sleeve top and instantly look put together.

• Toad & Co button downs: A bit more relaxed, but who can go wrong with a cozy flannel that’s also sustainably made?

For your feet

• Kizik Ashland slip-on boot: I have chronically cold feet, so slippers and insulated boots are a must for me, even while working from home. These are great because they’re both slippers and insulated boots (all rolled into one.) Their slip-ons are great, too!

• Bombas wool socks: I am a Bombas convert because these socks hold up SO WELL. I switch to wool socks when it gets cold, and these are my go-to when I want no-shows or ankle-level socks.

• Point 6 wool socks: These are actually cushioned wool hiking socks, meaning they’re super comfy and super warm. I have about 5-6 pairs of these and I love them so much.

Home Office Improvements

It’s getting cold out, so right now I’m all about my home office warm, cozy, and inviting. Here are some of the things that have helped me upgrade and optimize my workspace.

• This desk lamp: I like that this lamp has adjustable light color settings and varying brightness levels that I can change as the light transitions throughout the day.

• Heating pad: I keep this draped down the back of my desk chair, which helps with my back pain issues *and* keeps me warm.

• These battery-powered candles: Talk about hygge! Especially on rainy days, I love having the cozy lighting provided by these candles (that my pets can’t bump and burn the house down with.)

A few other favorites:

• A mini space heater: For the chronically cold who work in rooms with lots of (old) windows.

• Glasses with blue light blocking lenses: If you stare at a computer screen all day, these are a must-have.

• A whiteboard: This is where I keep my daily to-do lists, invoice tracking info, and all kinds of other things I don’t want to forget. It’s a life-saver.

Got Back Pain?

If, like me, you struggle with a lot of back pain from so much sitting in front of a computer screen while working from home, you might need these three things. They’ve helped me a lot (and I even travel with them!)

• Trigger point foam roller: At the end of the day, I roll out my back on this on the floor of my home office. It’s especially good for working the kinks out of the tight upper back and shoulder area.

• Textured massage ball: I like to roll this under my feet (a massage therapist told me this is supposed to help release lower back pain!)

• Massage gun: When my muscle pain gets severe, I break out the literal big guns. This is also great for when I’m doing lots of exercise and I’m sore from that activity.

Brain Fuel

• Verve coffee: Every single day I start my morning with either a cup of their Seabright blend or an latte made with their Streetlevel espresso. Never disappoints.

• Bub’s Naturals: I put a scoop of this brand’s collagen peptides or MCT Oil powder in my morning coffee because it makes me feel slightly better about all the cream and sugar I also add in.

• LiquidIV: On mornings when I feel dehydrated, I pop one of these packets into 16 oz. of water and I feel 100% better within about 15 minutes. Also great for post-exercise.

Books I Loved

If you spend a lot of time working from home, you probably need to escape to a good book. Of the books I read this year, these were my favorites.

1. The Lying Life of Adults by Elena Ferrante: This author is one of my all-time favorites for her ability to tease out characters’ emotions and to put you inside their heads.

2. The Order of Time by Carlo Rovelli: This was recommended by a friend on Twitter, and while it’s quite the technical/heavy read, for those of you who are also into the exploration of time and quantum physics…this is a fascinating book.

3. The Harvard Psychedelic Club by Don Lattin: I had no idea about the magic mushroom experiments that went on in the 70s at Harvard and the careers of these famous folks that emerged from it. Loved this piece of non-fiction!

4. French Exit by Patrick DeWitt: Writer Rachel Syme recommended this book as a fun story with larger-than-life characters, and it delivered. A quick, light read.

5. At the Existentialist Cafe by Sarah Bakewell: Looking for a crash course in Philosophy that doesn’t fly right over your head? This book is the approachable entry point you need.

6. Loving What Is by Byron Katie: I’m not a self-help book person at all, but this book jumped out at me from the shelf and was absolutely incredible. Should be required reading for all humans.

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What's on your most-loved list this year as you work from home?

I’m always looking for new things to try out, so tweet me @kaleighf and let me know what I should check out next.

For the sake of transparency, note there are some referral links in the mix here, but know that I haven’t recommended anything that I don’t personally use on a daily basis. Some of these items were purchased at full price, some were bought secondhand, and some I received as gifts from friends.

Goodbye MailChimp, Hello ConvertKit

Did you know I started writing and sending my newsletter via Mailchimp back in early 2016?

That's almost 5 years strong and more than 100 emails sent so far. The only time I’ve missed a send was when my husband and I went to Europe a few years ago (and even then, it was only delayed by a week.)

So, yes, I’m super committed to writing and sending these.

But it’s time for a change.

I’ll still be sending my newsletter every other week. The lessons aren’t going anywhere.

But I’ve decided to leave Mailchimp and switch to a new platform: ConvertKit.

About a month ago, I migrated over and have been watching my reports to see how performance varied. More on that in a sec, but first...here's why I decided to switch.

What made me decide to switch to ConvertKit?

• ConvertKit is better suited to my needs. It’s specifically geared toward online creators (that’s me!) and has some functionality that I’ve been missing out on with Mailchimp (like more in-depth reporting, better UX, and deliverability insights.)

• I’ve started writing content for the ConvertKit blog beginning in 2020, and with each post, I’ve learned more and more about what it can do (and what I was missing out on.) Plus: they’re a great team with amazing and helpful people. I saw the founder Nathan Barry speak at a conference session in 2016 and have been watching them grow ever since, and I super appreciate their transparency.

• Pricing. Mailchimp was more expensive than ConvertKit based on my subscriber count. This made switching kind of a no-brainer.

Migrating to a new email platform is no easy task (especially when you want to be sure to protect your subscribers and are learning the ins and outs of a new tool.)

BUT! I loved that ConvertKit does offer done-for-you migrations where they’ll move your subscribers over (which is really handy.)

I was also fortunate to get linked up with Jason Resnick who is a PRO at all things ConvertKit and helped make sure I optimized my setup there.

I hate when people send these type of hyped up email platform migration announcement emails because really...like, who cares?

So I wanted to add a bit of context so you know why I'm sharing this. It's alllll about the difference I've noticed in sending from Mailchimp vs. Convertkit.

Mailchimp vs. ConvertKit

This is my report from Mailchimp showing my historical average email campaign performance:

On Mailchimp, my open rates averaged about 40% for the last year and click rate about 7%.

This, in contrast, is my report from Convertkit, showing the performance of my welcome email series from the past month.

Notice the ~75% open rate and ~34% click rate.

Pretty remarkable, right? I think it has a whole lot to do with deliverability, a report on which you can see below from my ConvertKit Pro account.

It’s still fairly early to report back on the big-picture performance of my newsletter broadcasts as I only send them out every other week, but I can share some of the cumulative reporting insights from the first few I’ve sent so far:

1. 65.1% Open Rate, 13.3% Clicks

2. 45.9% Open Rate, 6.1% Clicks

3. 65.9% Open Rate, 26.8% Clicks

4. 50.4% Open Rate, 5.0% Click Rate

Again, you’ll notice that both of these engagement metrics are significantly higher since switching to ConvertKit (which makes me very, very happy.)

You can expect business as usual from my newsletter moving forward, and my hope is that from now on, my updates will be even more relevant to your interests.

P.S. If you’re thinking about starting a newsletter or switching to ConvertKit from another email platform, be sure to take advantage of their free trial and test it out to see if it’s a good fit for you.

2019 In Review

This year I celebrated six years of full-time freelance writing, and it was my most productive and interesting year of self-employment to date.

Client work picked up, Paul Jarvis and I partnered on the Creative Class course and podcast again (cracking 100K downloads!), and I still find myself excited when I sit down to work each day. I’m so grateful to have found a job I enjoy doing and am truly interested in…the novelty of that never wears off.

This year I also leaned into writing about direct-to-consumer retail and sustainable fashion, which started as an outlet for my interests but transformed into a whole new world of connections, opportunities, and friendships. Writing for publications like Forbes, Adweek, and Glossy opened doors to conversations I likely wouldn’t otherwise have had access to and gave me a place to share my expertise on eCommerce in a new way. Win-win.

What else happened in 2019?

The Domina Retreat for Female Freelancers

In April, my friend Emma Siemasko and I hosted our first ever retreat and brought together a small group of women at an Airbnb just outside of Austin, Texas. I wrote up a full recap of that if you want more details on what it was/how it went, but in short: I’m so proud! It was a wonderful time, and Emma was the perfect partner to do this with. Face time with these smart women was incredibly valuable for me.

More Freelance Writing Coaching

This year I continued my one-on-one freelance writing coaching work (year three!) and I loved having the opportunity to work with more international freelance writers, including a few living in India, the UK, Australia, and Japan. While the time zones made scheduling a little tricky, we always made it work! I also got to meet up in person with a few of my past coaching partners. I love that some of these business relationships have blossomed into real friendships over the years.

Freelance Writing Business Performance

My busiest months this year were January through April and October through December, which worked out well because it allowed me to enjoy the summer months and do some non-work travel during that time.

I brought on some incredible new freelance writing clients like Monday.com, Packlane, Freshworks, and ChurnBuster while continuing to work with some of my long-standing SaaS/eCommerce clients as well. Again, I am so grateful to have had some fellow freelance writers support me on different projects, which helped me stay sane. I didn’t surpass my freelance business revenue from last year, but I’m really happy with what I invoiced over the past 12 months.

A huge perk of living in the rural Midwest and working with clients in major metropolitan markets is that the low cost of living here means higher margins for me. The trade-off is that we’re not really close to much and travel takes longer. Pros and cons, just like everything in life.

Other highlights:

• Started teaching yoga. I’ve been going to classes for years now, but when a local studio opened up this spring I got the chance to start teaching a morning class of my own. I’m loving it!

• Joined the “Friends of the Library” Board in my hometown. So far I’ve gone to a 20-minute meeting and been asked to make cookies for children’s story time. Best Board gig ever? I think so.

Work Travel, Life Travel

2019 was full of travel again. I was in LA twice this year: Once for a fun trip with my husband and our brothers, and once to attend Yellow Conference. Both times I went to Rosie’s dog beach in Long Beach, which is pretty much my favorite place on earth.

In September, Brandon and I went to Colorado to participate in the Fjallraven Classic: A three-day, 25-mile trek through the Rocky Mountains. Despite some training beforehand, it totally kicked our flatland Midwestern asses. Carrying our 30+ pound packs, we ended up walking for 8-9 hours each day (because, well, we were slow.) It was both physically and mentally challenging, but I mean…look at those views. You can’t really complain when you’re looking at these gorgeous landscapes.

The entire trek was so beautiful, and the people we met during the event were the best, cheering us on the whole way. The community this event brings together is incredible and everyone was so kind. I never thought we’d climb a mountain, but it was an amazing experience and I’m glad we did it. A Snickers bar at the summit of the highest peak never tasted so good.

Seattle was one of my most favorite places we visited this year for the first time. Brandon and I spent a few days exploring the city, hiking, eating all the food, and even took the ferry over to sleepy Bainbridge Island. There were so many dogs, the people were great, and we found this city to have a very ‘livable’ feeling to it. My big highlight was having pastries at a little coffee shop on a rainy/foggy day. So relaxing.

We took Brooks north to Racine, Wisconsin not once but TWICE this year on his own little adventures where he got to splash around in Lake Michigan, stay in a hotel, and go to the fancy dog park in the Chicago suburbs on the way back. Clearly he had a very good time.

Other travel highlights:

• St. Louis: This is the closest city to us, so we visit it often. In 2019 we had amazing stays at both the Angad Arts Hotel and the newly remodeled Union Station. If you’re in the area, I can’t recommend these hotels enough. Very cool.

• Fermilab: I toured the particle accelerator at Fermilab in Batavia, Illinois (and the nerd in me loved it.)

• Boston: Brandon took another executive education course this April, this time at MIT. I tagged along and worked remotely from Boston, and we both loved how walkable the city was. Also went to my first baseball game at Fenway Park!

• Chicago: I took a couple of trips to Chicago this year both for work and pleasure. I loved getting to check out the Wicker Park neighborhood while I was in town for a 2PM Executive Members dinner and again just about a month ago while we were in town for a sustainable holiday market. This Airbnb and The Robey were both *so* lovely!

Favorite reads

As usual, I put my library card to good use this year. My top five reads were:

How to Change Your Mind by Michael Pollan: Interesting look at psychedelics, the stigma associated with them, and new research that indicates they can be beneficial in new contexts.

The Great Pretender by Susannah Cahalan: I loved Cahalan’s first book Brain on Fire, and after my husband and I saw her speak about her newest book in St. Louis, I was hooked. Quick read with a fascinating look at mental healthcare over the years and one very unique study.

Daisy Jones and the Six by Taylor Jenkins Reid: A fun, easy read with strong characters who are rock star band mates. I can’t wait to see this made into a TV show.

Bitter Brew by William Knoedelseder: If you liked the show Succession, you’ll like this book. It’s the true story of the family behind Anheuser-Busch beer...and it’s a roller coaster.

Lost and Wanted by Nell Freudenberger: This was an oddball fiction choice for me that I just happened to pluck off the shelf at the library. I loved it: Thoughtful and extremely well-written.

Goals for the Year Ahead

A theme for me in 2020 is stepping out of my comfort zone as a freelance writer.

For a long time, I’ve held a very anti-conference/speaking stance because 1) traveling to speak isn’t often a lucrative activity and 2) it takes a lot of time and energy. Public speaking still gives me the nervous sweats, but this year, I want to challenge this point of view.

I’d like to dip my toes in the water by participating in more panels and maybe even doing more speaking/moderation, especially on topics about retail, eCommerce, direct-to-consumer brands, and sustainable fashion.

If that doesn’t pan out, I’m at least going to make an effort to be present at more gatherings where my internet friends/peers are meeting up in person, because I’m finding that those face-to-face meetups are some of my most favorite/impactful experiences for my business.

Did you do a post like this—or do you have an accomplishment from 2019 you’re really proud of? I wanna hear about it. Tweet me @kaleighf.

This originally appeared in my newsletter, A Cup of Copy. Sign up and get future editions delivered to your inbox.

Best Tips for Getting Ahead in Your Freelance Writing Career

Earlier this week, I spoke to a class of high school seniors in an entrepreneurship program.

I got into how connections, networking, and relationship-building got me from an e-commerce store launched on a whim in college to a full-time freelance writing career.

But I think the most important thing I shared was on my last slide. You know...the major takeaways.

So what were they?

Never stop learning; always be curious.

Loving to learn and a curious mind has helped me become a better researcher, writer, and overall better communicator. If you can dedicate yourself to always taking in new information (and learning from it) you’ll have a leg up over a good majority of folks who are content with flying on autopilot mode into adulthood.

Find people who are doing what you want to do and ask them questions.

If you can find someone who’s willing to take you under his or her wing and can share insight on how they got to where they are, you’ve discovered a brilliant shortcut when it comes to getting from where you are to where you want to be. Not only can they help you avoid some of the mistakes they made, but they might even be willing to take you on as an apprentice--which can be an incredible hands-on way to learn.

Make friends, be nice to people.

I got into working with software companies because I connected with an editor (Emma Siemasko!) over Twitter. She commented on liking a piece from my e-commerce store, and so I offered to send her one for free. That back-and-forth then moved to email, and she eventually ended up hiring me as a freelance writer. The connections grew from that one conversation. To me, this is a major testament to making friends (and generally being a nice person!)

Raise your hand and say so when you have a good idea.

It’s easy to sit in the shadows and never speak up. It’s much harder to say, “Hey, I have an idea on how we can do X, and I can help by doing A, B, and C.” However, if you do it and go out on a limb by speaking up, it can lead to major opportunities. For me, it’s how I ended up co-teaching the Creative Class, a course for freelancers, with Paul Jarvis. I say swallow your fears and say so when you can bring something valuable to the table. The worst that can happen is the other person will say no.

Be honest with yourself about what you’re good at (and what you’re not.)

I always used to beat myself up that I wasn’t a math person. It made me feel stupid and I was frustrated that my brain didn’t work that way. But then I realized when it came to words--that was my forte. And it was okay that I wasn’t a math person. Being honest with myself about where I excelled and where I didn’t simplified my life and business by allowing me to outsource things I’m not good at--and it helped me find a career I truly enjoy, too.

Eight hours a day is a long time to spend doing one thing;try to find something you enjoy.

I wish someone would’ve told me this when I was in college. When you’re spending 40 hours a week doing something, you better like it--because that’s where a good chunk of your adult life will be spent. That doesn’t mean you have to go out and find your *dream job.* But it does mean that the path you choose should be rooted in something you enjoy and can fully lean into.

Make stuff even when you’re not entirely sure what you’re doing.

I’m a do-er. I don’t think too much about details and process when it comes to creating--I just go, full steam ahead. This maker mentality is how I launched my first business, helped me get my first freelance gigs, and ultimately led to the incredible career I have now. Making/launching things is scary and hard, but I say just GO and perfect it along the way. Don’t get stuck in the planning stage. Make, tweak, repeat.

These reminders aren't just good for high schoolers; they're good axioms for anyone. They're especially helpful if you're looking to change gears and shift into a new career or life direction.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.

Reflecting on Six Years of Full-Time Freelance Writing

Back with another personal update this week.

No writing lesson, but if you missed last week’s post on how to vary your writing voice, that’d be a great one to check out.

So what’s new around here?

Well, in a few short months, I’ll be coming up on six whole years of full-time self employment. That’s really wild.

What’s it like freelance writing?

It feels like yesterday that I graduated college and started my PR job for a local non-profit.

I was there for two and a half years, so really, that means I’ve been working on my own twice as long as I’ve worked in an office setting.

Now, there are a lot of wonderful things about working alone and from home on a freelance basis. The perks are very real, and I’m so grateful for them.

Positives of Freelance Writing

I get to set my own schedule, which means it’s often as flexible as I want it to be.
I can get up and start my day whenever I want (or sleep in a bit if needed!)
I can work extremely efficiently with zero interruptions.
I wear sweatpants most days.
I can challenge myself to earn more because I’m not on a set salary.
I get to hang with my dog Brooks and take breaks to walk him when I feel like it.
I can cook tasty lunches in my kitchen (even though I don’t very often...I’m bad at this.)

But there are also some major drawbacks to this type of work life, too.

Negatives of Freelance Writing

There are no real co-workers to vent to on a rough day or to celebrate with when things go right.
Some days I go a full eight hours without talking to another human out loud.
Living and working in the same (small) square footage can get really monotonous.
With most of my work being digital, much of what I create feels intangible.
There’s stress that comes with the ebb and flow of work, which is mostly out of my control.
Sometimes not having a set salary opens the door to endless self-competition (which isn’t super healthy.)

I’ve been thinking a lot about the pros and cons of this lifestyle I’ve been living lately as I talk to friends and fellow freelancers who are now entering different life stages.

Some are having their first kids. Some are moving. Some are buying their first homes. It feels like a period of transition for a lot of people around my age right now (those of us who are shifting out of the late 20s and into the early 30s) and it generates a weird feeling.

As of right now, my life is pretty stable. No big changes on the horizon. It’s business as usual.

But I find myself wondering, “Am I doing the right thing? Am I on the right path?”

Existentialism and Freelance Writing

This is all really more of an existential question rather than one rooted in unhappiness or malcontent, but it’s there nonetheless. And I’ve been wrestling with it for a while.

Maybe you’re in (or have been in) the same boat before. The water is choppy. I’m feeling a little seasick (to get reaaaal heavy on the metaphor.)

I’m working on figuring out what the answer looks like for me, but I feel like it’s time for something different. An added challenge or a new goal to strive for.

Until then, remember to be nice to yourself. And keep writing.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.

The Domina Retreat for Female Freelancers: A Recap

Earlier this month, I co-hosted my first ever women’s business retreat with fellow writer Emma Siemasko. We called it the Domina Retreat, and for two and a half days we spent time learning, sharing, and relaxing at a beautiful Airbnb home on Lake Travis just outside Austin, Texas.

Emma and I, both working as freelance writers and independent consultants, had been getting together once a year to co-work and brainstorm ideas since 2016. But this year, we decided to open things up a bit and invite other women to join us for a small retreat.

It was always a highlight of the year for us to get face time with another person who truly “gets” what we do, so we figured that there must be other women out there feeling the exact same way–longing for community.

Turns out, we were right. This year, our small group included 16 female freelancers, consultants, and entrepreneurs who traveled from places as far as Japan, Hawaii, and Canada to be there.

Our first retreat for female freelancers

I’d be lying if I said I wasn’t nervous going into this event. Even with a fantastic partner and lots of planning, I still worried that something would go wrong. I spent a few nights losing sleep over silly questions like:

• “What if people hate the food and go hungry?”

• “What if people don’t talk to each other or are bored?”

• “What if someone gets hurt while they’re at the house?”

The good news is: None of those things happened. But this worrier mentality did help my partner and me think through the details and create some plans that made us both feel more secure going into the event.

Emma gathered some information about hosting successful events from Jessie Char, and I spoke with Dorie Clark who offered some great tips on planning and executing business retreats.

Tips for a polished freelancer retreat

These activities helped us come up with a few elements of the event that really made it feel more polished, such as:

• An amenity table with travel-sized items, personal care, and office supplies for anyone who needed them

• A big supply of drinks, including lots of bottled water and La Croix

• A general script for our welcome speech that explained the ‘why’ behind the event, that positioned us as capable leaders, and that outlined our goals for the days ahead

• Take-home bags with personalized, handwritten thank you notes

And guess what? From the very first night of the retreat, things went smoothly. Everyone loved the location, we ate pizza, and people introduced themselves, chatting in small groups around the house. Our location had lots of great areas for mingling both inside and out, and everyone fell in with each other naturally.

Over the next few days we had a few more structured sessions during the event:

• Tracey Wallace shared her expertise on everything from networking to technical SEO for content writing

• Linda Perry led a session on limiting beliefs and business growth

• I did a session on using Twitter for networking and finding opportunities

• Emma shared her onboarding and pitching process, then lead a goal-setting workshop

• Emma also led our business book club discussion where we talked about The Four Tendencies by Gretchen Rubin (which was great for getting to know each others’ personality types) and business “hot seats”, wherein each person was able to present a question and gather feedback on how to solve problems within their business. Our post-event survey showed that the hot seats were one of the most-loved activities.

What worked well for our freelancer retreat

So what worked well about the retreat?

1) Balanced activities

Our agenda for the retreat was focused on striking a balance between group activities and private work time, during which attendees could co-work in a shared space or go off and do their own thing (whether that was swimming, taking calls in a private room, or going back to their hotel room to work for a bit.)

We wanted there to be some autonomy around what people could do while they were there rather than scheduling everything down to the last detail, and that served us well. While it freed people up to enjoy their time at the house, it also made time for unstructured conversations and networking between attendees–which was great.

2) Time outdoors

We were fortunate to have some excellent weather while we were in Texas, so I’m glad we had a couple of outdoor activities scheduled and available during the retreat. Miranda Hanna, one of our attendees, lead an hour-long morning yoga class on the lawn one day, and the next morning a small group hiked at Mount Lakeway trail. We also took a sunset walk one night after dinner as a group, which was a relaxing way to wind down the day.

3) The group

This group of women all specialized in creative work, but specialization varied quite a bit in regard to work type: We had graphic designers, writers, coaches, consultants, and even an interior designer. The amazing thing was that despite the fact that our day-to-day work didn’t always have a ton of overlap, this group really connected well on a personality level and just naturally gelled.

Everyone was kind and respectful, and because they were there for the right reasons (and had paid to be there), they were open communicators who showed true interest in learning from and listening to the other women they met there. Emma and I worried a bit that we’d need to lead a lot of the conversations to avoid awkward silences, but we didn’t have to do this one bit. It was amazing to sit back and see the group sharing with each other all on their own. It seemed to us like everyone made the most of their time and squeezed as much value as possible out of the days we spent together.

What we’ll improve for our next freelancer retreat

Were there some things we could improve upon? Of course.

1) Smaller food orders

Emma and I wanted to be sure we had plenty of snacks and drinks for everyone, and we also provided breakfast for everyone on two of the days, so we went to Costco and really loaded up. We did end up having quite a bit left over, but thankfully we were able to send some of it home with a few women who lived in Austin or were staying in the area.

Our meals had quite a bit of excess as well, but I guess it’s better to have too much rather than not enough. Next time we’ll know to cut down our orders a bit and maybe skip Costco, going for a regular grocery store rather than Costco-sized portions on everything instead.

2) Offsite overnights

One thing Emma and I agreed on was that next time, we’ll probably opt for offsite overnight lodging outside of full bedrooms located in our home base. We offered the downstairs bunks as a more cost-effective option for a few attendees this time, but felt like after an all-day event like this one was, it’s nice to have a private room with a door that can close so you can fully decompress at the end of the day. While we didn’t have complaints about this from those who went the bunk route, we both agreed this would probably improve the overall experience.

Emma and I also agreed that, as event coordinators, this change would give us the chance to regroup at the end of the day to talk about what was working well, any snafus, and what needed to be done for the next day logistically. With this setup, we didn’t really have time or space to do that.

3) Transportation

We discovered Uber wasn’t very reliable in the area where our Airbnb was the week before the event. It was out of our control, but it would’ve been nice if we had anticipated this ahead of time. That way, we would’ve been able to share the transportation details ahead of time, which would’ve eased some anxiety. I ended up getting an extra rental car for us to have on hand through Turo, but fortunately most people had their own cars and/or figured out carpool options with other people coming to the event. We also offered a shuttle to the airport on the last day, which helped simplify logistical concerns for folks as things wrapped up.

The value of having partners and sponsors

We wouldn’t have been able to pull off this event without some incredible partners who came to the table ready to support this smart, talented group of women.

These partnerships came from existing relationships I had with founders and CEOs–some from ongoing Twitter conversations, some from my reporting work. I reached out, explained what we were doing and why it was important, and made a modest ask. All of them immediately said, “Yes, this is great! How can we help?” (Ah, the power of online friendships.)

Coywolf and Noko were our meal sponsors, and the lovely folks behind these two companies stepped up to provide dinners for our guests (authentic Texas BBQ one night and a chef-made meal the next.) Both were delicious.

Along with those lovely meals, we also had a variety of ice cream pints delivered to the house from our friends at Jeni’s Splendid Ice Creams and a some champagne and gin sent over from Taster’s Club. Yum!

Creative Class and Freelance Mastermind both provided a diversity and inclusion ticket, so we were able to bring in two extra attendees from under-represented communities and had those valuable perspectives at the event.

Two people in particular were extra crucial: Becca Matimba stepped in as our event coordinator, handling lots of logistical to-do list items and generally was the behind-the-scenes wizard that made everything go smoothly. Tanialee Gonzalez was our event photographer, and she got some amazing photos plus offered to take headshots for anyone who was interested.

Takeaways (literally!)

We also had a take-home bag for each and every attendee, which included fantastic things like:

• Verve coffee drip kits

• Original Human serums

• Krit stickers and a discount offer

• Prints from Archer & Olive

• Shawn Askinosie’s book Meaningful Work, plus a bar of Askinosie chocolate

• Ettitude sleep eye masks

• Shades Club sunglasses

• Odds & Sods Austin ‘ATX’ pins

• Highway Robery tiny drink robes

• A LavishGOLD discount offer

• Bags from AJ&Smart

I also have to give MAJOR kudos to my retreat planning partner Emma, who was nearing her third trimester in her pregnancy during this event but was full of energy. High five to her for being up for this–she never complained once! A great leader and entertainer, she was the perfect person to partner with for this as our skills and work styles were (and still are!) very complementary.

Final Thoughts on Our Freelancer Retreat

Overall, the retreat wasn’t a big money-maker for us, but we both went in expecting a low margin and really just wanted the chance to bring some smart women together that we could learn from. This was both of our first experience hosting an event, and I’m extremely proud of how it turned out.

The biggest thing I walked away with from our first-ever retreat was, aside from a sense of accomplishment, a real appreciation for the group of women who came together. Not only did I learn some valuable lessons and set goals for my business, but I also made new friends. As corny as that sounds, that’s hands-down the best thing I’ve done for my business in my nearly six years of running it.

Here’s to hoping we’ll do another female freelancer retreat in the next year or two.

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This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.

The Post-Holiday Blues

I love the holiday season, but I dread when it’s over.

For someone like me that works alone (and has a lot of quiet time to myself), I look forward to having friends and family home for the holidays. It’s so different from my normal day-to-day.

I love the transformation that happens when our house is full of people and there are a million different conversations all happening at once. There’s so much life! And noise! And excitement!

But every year, right after the holidays, I find myself in a rut.

Our house goes back to its quiet state as people go back to their own homes, and all that’s left is another three to four months of gray, bleak winter ahead of us. Not to mention it’s the end of the year, which is naturally a time of reflection. It compounds things a bit.

As a result, I find myself feeling pretty sad, and for the past several years, I’ve really struggled through the first few weeks of January as I try to get myself back on track with “normal” life and work.

After tweeting a similar sentiment last week, I thought it’d be good to talk a bit about this--and if nothing else, it might serve as a reminder to anyone else who’s feeling the same way.

You’re not alone, and I can tell you that at least for me, it goes away with time. It does get better.

I’ve written before about how I often find working from home (or at least independently, without co-workers) isolating at times. I saw a study recently that showed loneliness is the #1 drawback of freelancing. I believe that.

For me, living in an especially rural area, I feel like it’s even harder during cold winter months when:

1. I don’t want to leave the house because it’s so cold
2. There’s not a lot else going on anyway

However, this year I’m at least trying to be mindful of the fact that I know the post-holiday blues are pretty normal for me--and I’m working to anticipate that. I’ve found that keeping busy is a good distraction, so I have plans to:

Work through the list of library books I’ve been wanting to read

• Take a few classes on MasterClass and learn some new skills

• Find out how I can volunteer at the local pet shelter

• Continuing to work on things for the Domina Retreat

In reality, there’s no magic wand I can wave that’s going to make it all better.

It’s a work in progress, and I think just being aware of the fact that it happens is a good start.

If you're dealing with the same: Hang in there.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.

Recap: Five Years of Full-time Freelance Writing

Five years ago this month, I left my full-time job in PR to try freelance writing full time. I gave myself 18 months to see if I could (in the words of Tim Gunn) MAKE IT WORK.

Long story short: It’s still working. I’m still out here, freelancin’ it up.

I feel like this is a big deal. I’ve officially been freelancing longer than I’ve been doing any other job. It’s also longer than I’ve ever kept a pair of shoes.

But the thing is...when you work alone, from home...largely by yourself...it feels like there’s no one to celebrate these milestones with you. Ya know?

If I worked in an office, we’d at least go out to lunch to celebrate or eat some crappy ice cream cake. (Ice cream cake is gross. Just saying.)

So, I decided I’m going to reflect on the past five years with you guys. Okay? You don’t even have to buy me lunch.

Recap: The Highlights From 5 Years of Full-Time Freelance Writing

2013

• Started with 2 contract clients for social media management

• Tried a lot of different types of writing work for about 234,135 different industries

• Made more than I had been making in the PR job (whew!)

• DIDN’T QUIT (first year was so intimidating/challenging)

2014

• Spoke at local conferences/associations on social media

• Started to realize I didn’t love social media management

• Took the Creative Class and decided to niche down, focusing on blog content for SaaS/eCommerce companies

• Outsourced taxes/financials to a real life accountant and set up a retirement plan

2015

• Spent part of the year traveling, presenting, and teaching social media (only to definitively realize I don’t like doing that)

• Introduced the KaleighMoore.com site (shoutout to my husband/biz partner Brandon for building that for me)

• Launched THIS NEWSLETTER shortly thereafter

• Went to my first conference as a freelancer and met up with my pal Emma for some co-working in Austin

2016

• Formed a business LLC

• Got real comfy in the SaaS niche

• Finally learned to say no to projects that weren’t a good fit

• Took some amazing trips

• Introduced one-on-one coaching for freelance writers

2017

• Started Creative Class revamp with Paul Jarvis

• Co-hosted my first podcast (still am!)

• More lovely international travel

• Officially put myself on a salary

• Worked really hard to establish better work-life balance

• Launched Yeah Write Club

• Took another co-working retreat with Emma
  

Pros and Cons of Freelance Writing Full-Time

What’s been great vs. what’s been sucky so far:

GREAT THINGS

1. Freedom and flexibility. Holy crap do I love choosing when I get up in the morning. And wearing whatever I want all day (ahem, pajamas). And being able to take my dog on a walk when I feel like it. That is a major perk that I still pinch myself over every day.

1. Opportunities galore. I’ve found that if you’re a do-er and are good at the thing you do, freelancing presents so. much. opportunity. You can earn a lot, work with amazing clients around the world, and if you’re efficient, not be chained to a desk for eight hours a day.

1. The people. I’ve been fortunate to get to know some very smart and interesting freelancers over the past five years (who I wouldn’t have known if I weren’t freelancing.) So thankful for a handful of friends who “get it” and can relate with this type of work, who act as a sounding board, and who occasionally serve as co-workers when I need to vent.

SUCKY THINGS:

1. It can be lonely. I’ve talked about this a lot before. The bottom line is I never realized how important human interaction was for me until I didn’t have it anymore. I’ve found some ways to circumvent this and am feeling a lot less isolated these days, but it’s something I have to be mindful of so it doesn’t sneak up on me and give me the sads.

2. No guarantees. I’ve been fortunate to have a freelance career that’s progressively grown over the past five years, which I think is thanks to hard work and a lot of luck. However, there are no guarantees that this will keep up. I never know how much I’m going to make each month, for example. Sometimes I do miss having some certainty, but so far, I’ve been able to leverage the uncertainty as fear...and that fear keeps me working hard and pushing forward.

3. It’s hard to explain freelancing to other people. Five years in and I still haven’t figured out how to tell other people what I do (in a way they’ll understand.) It’s frustrating when people associate freelancing with scraping by, ‘not real work’, etc. Still working on this one.

The big picture: Freelance Writing as a Career

I think, looking back, there are a few big things I’ve learned over the past five years of freelance writing.

For one thing, I’ve learned a lot about myself. I spend a lot of time in my own head. There are pros and cons to that, just like with anything else, but it’s given me the time and space to figure out what’s important to me, what I do and don’t like, and what ‘works’ for me as a person and as a business owner.

I’ve learned things like:

• I have to build group activities into my life. Be it yoga class, Skype chats, whatever...my brain is healthier when I make it a priority to be sociable.

• I have a tendency to over-work. Building boundaries into my process (like office hours, restricted phone time, etc.) helps keep me from being “on” all the time.

• I don’t enjoy speaking to large groups. Talking to a big room of people makes me SO nervous that I can hardly eat or sleep in the days leading up to the event. Not cool.

• Conferences aren’t really my jam, either. I don’t like having to be in a certain place at a certain time. I’d rather just meet up with people afterwards for dinner.

• I’m very into collaborative efforts. I do well in a setting where not all of the responsibility for a project is on my shoulders and like a small team environment (largely in the world of things like ‘let’s make a thing!’ or ‘let’s plan an event!’)

I’ve also learned that I am not great at thinking about the future. Give me a to-do list and I’ll knock it out right away...but ask me where I see myself a year from now and I’m all ¯\_(ツ)_/¯

That’s where I’ve been really fortunate to have a partner who is good at future-thinking. I’ve never had a formal business coach before, but Brandon (husband) has filled that role for me. Over the past five years, he’s encouraged me to do important growth-related things, like setting goals for myself (Ex: Try to get three bylines in major publications by X date), learning (he told me about Creative Class), and sticking with long-term efforts...like this newsletter.

I think it’s important to find someone like that who can help you work through those important questions, like:

• What kind of work do you actually enjoy doing (and want to do more of in the future?)

• What steps do you need to take to get to that point?

• What things are you not doing right now that maybe you should be?

• Are you challenging yourself?

• Are you taking care of yourself outside of work?

In general, having someone who keeps you accountable and forward-thinking means you’re building in sustainability to your business. It’s helped save me from burnout and motivates me to try new things.

Will I still be freelance writing five years from today? I dunno. But I’m happy with how things have gone up to this point.

It’s hard work, but it’s also rewarding.

Speaking of rewards...I think I’ll treat myself to a spa day now. 💆

P.S. S3 of Creative Class podcast is live! YAY!

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.

Insights on Productivity & Freelance Writing

A few weeks ago, I shared a master list of everything that’s helped me freelance and write for the past four years on Twitter.

From software tools to the convertible standing desk I use--it’s all there.

But then I was video chatting with my friend Val Geisler.

I mentioned to her how much I love virtual conversations like the one we were having, and how I had been wrestling with a need to get out of the house and feel more connected lately.

She said something to the extent of how it was funny that even with my ideal workspace setup at home (with everything I need to be highly productive)--I still had this urge to get out of there.

That was a lightbulb moment for me. She had a point.

I realized that even with the best tools, the comfiest chair, and a WHOLE ROOM dedicated to work, there was still a missing piece that was keeping me from being 100% laser focused on my freelance projects.

And it had to do with me.

Not the tools. Not the desk.

I needed to think beyond the tools and resources and address the internal aspects of freelancing and owning a small business to get to a better place.

After some reflection, here are two big takeaways that came from this line of thinking. Maybe (hopefully) they will help you, too.

Number one: It’s important to test what you know about yourself.

We all feel like we generally know ourselves, right? We know what we like, what we don’t like, and what we’re good at.

I felt this way, too--but I wanted to test my assumptions and double-check.

I started with two different personality assessments: The Strengths Finder and the PDP.

These personality tests confirmed a few things for me (like my love for learning and my poor ability to handle criticism.)

But I also learned that I am highly extroverted--which was kind of surprising to me. I spend most of my time working alone--and as a result--I’d started to think of myself as an introvert. Wrong-o.

These findings were a good reminder that I actually thrive when working and interacting with others. It also reminded me I needed to be better about getting out of my home office and scheduling facetime with other human adults. I had let that slip a bit and was quickly sliding into winter hermit mode.

The good news is I’m already taking steps to act on this and am putting myself “out there” more.

- In February, I’ll be doing a test run with a local co-working space. It’s only a few blocks away from me, has huge windows (yay!), and is shared by just a few other female business owners.

- In recent weeks I’ve been going to a new aerial fitness class. So far the class size has been super small (it’s not an easy class!) but I’m hoping that I’ll get to know some of the people there better in the coming months. If nothing else, it gets me out of the house.

- I also reached out to the local library and am leading some free resume-writing classes (in person). I don’t love public speaking, but I wanted to put my writing skills to good use in a way that could help others. The first one went really well last week and there were lots of good questions from attendees.

But that's not all. There was something else I realized...

Number Two: It’s important to gain some mental control.

When you work alone (or when you’re the boss), you spend a lot of time inside your own head.

There’s a lot of responsibility that falls on you on a day-to-day basis, and it can be easy to let your monkey brain take over--constantly hopping from one thought to the next during every waking moment.

It causes a cycle of anxiety and stress that can eat away at your focus during the day and can generally make you an unpleasant person (speaking from first-hand knowledge.)

For a long time, my “monkey brain” was especially bad when I’d lay down and close my eyes to sleep at night. My brain would kick into high gear, cycling through the day’s problems, tomorrow’s to-do list, my anxieties around forward momentum and long-term plans, etc. etc.

But it wasn’t until I stepped back and thought about this that I realized how much damage the never-ending cycle was doing. It was affecting my personal life and my work.

So, again, I’ve been taking steps to work on this. Here’s how:

1. Setting up a good sleep routine.

Brandon, my husband, has to live with me and has seen the effects that poor/no sleep have on me, so he suggested we set up a nightly routine to help me prepare my brain for sleepy time each night.

And guess what? It works.

Here’s what it looks like:

• Put down the phone (and don’t look at it!) after 9:30 p.m.

• Prepare the bedroom for sleep. I turn on my white noise machine, close the blinds and curtains, and turn down the sheets so I can basically sleepwalk into bed.

• Turn off all the lights and put on a “boring” show in the living room. (I’m a big fan of Rick Steves, BBC docs, or ASMR videos for this. I don’t think they’re boring but they’re not character-driven stories you can get wrapped up in, ya know?)

• Then, when I’m nice and sleepy, I just walk a few steps into the bedroom and basically fall onto the bed.

• Wake up at the same time each day. My FitBit alarm goes off at 7:30, and I’m out of bed by 8:00 at the very latest.

Following this routine has made major improvements in my sleep quality--and it’s almost completely eliminated my nighttime ruminations. Plus: Better focus during the work day and far fewer problems with chronic migraines.

2. Experimenting with meditation.

I’ve been doing yoga for years, but I’ve never been particularly good at the meditation part.

I mentioned in the last newsletter that I’ve been reading a book on the topic, so now that I understand what meditation is really about, I’ve been giving it a second shot with the help of Headspace. There are lots of apps/tools you can use for guided meditation, and I think having some guidance goes a long way.

I have to say, even as little as 3-5 minutes a day has been helping me get better at observing my thoughts rather than being engulfed by them. I have a lot of work to do, but practice makes perfect, right?

The lesson: Even the best setup won’t fix everything

To summarize: It’s easy to buy the stuff that helps us be more productive and fulfilled during our working hours.

You can set up the ~most baller~ workspace possible, but to be truly focused and productive, there’s still a lot of internal work to do, too.

It’s not easy. It’s not always fun.

There are still days when I have ZERO desire to meditate for even three minutes. There are DEFINITELY days when I don’t want to get out of my pajamas and go meet someone for coffee. At all.

But (for me at least) doing these things is just as important as getting a new computer or finding the perfect workflow for writing. Maybe more so, in fact.

My challenge for you: If you’re not doing any (or at least some) of these things already, make some time this week for it.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.

2017: A Year of Freelance Writing In Review

My fourth year of freelancing just wrapped up, and it’s time to look back on everything that happened in 2017.
 
I do these reflection posts each year, so you can read recaps from 2015 or 2016 if you’re interested.
 
Here’s what this year was like.

New Things, Big Projects

This year, one of my biggest projects was working with Paul Jarvis to re-vamp the Creative Class, a course on the business side of freelancing.
 
I took the course myself back in 2014, so when he sent out an email this spring asking for feedback on how he could improve the course in V2, I responded with a few ideas I had. He ended up bringing me on as a co-teacher/editor/partner, and over the summer, we re-built it from the ground up.
 
We also created and co-hosted a brand new podcast and are getting ready to host our first live, interactive productivity workshop in January.
 
I worked with a few fantastic writers this year who participated in my one-on-one coaching program—I’m so proud of the progress they’ve made and am constantly blown away with the work they’re doing.
 
Aside from this, I continued to write a boatload of blog content for a pretty regular group of clients in the SaaS and eCommerce worlds—brands like Campaign Monitor, GetFeedback, and SnapApp (to name a few). My annual revenue was down about $16,000 total from last year, but I’m happy with the decision I made to take on less work and enjoy a bit more freedom and flexibility this past year (more on that later).
 
When I wasn’t writing, teaching, or coaching, I popped up in a few new places:

• Unemployable with Brian Clark (podcast)

• Copyhackers: Tutorial Tuesday (live tutorial)

• GetUplift webinar (live training)

And in September, I had the opportunity to write a bit about my experience as a female working in the freelancer/tech space over on the Jennifer blog. Paul and I also discussed this topic in depth on the podcast, and I hope to continue these conversations into 2018.

I’ve stuck to sending out my newsletter 2x per month (as promised!) and plan on continuing that into the year ahead as well. I can’t believe this is year three of it already. 😮

Hobbies

Spanish/Guitar Lessons: Early in 2017, I was regularly taking both Spanish and guitar lessons—something to keep me from having idle hands during winter months. I didn’t end up sticking with either, though—and it pains me a bit to admit that. As soon as it started to get warmer, I fell off with both. I guess a little practice is better than none…
 
Reading: I read a ton of great books this year. Some of my favorites were:

• Sweetbitter

• Hillbilly Elegy

• Dark Matter

• You’ll Grow Out of It

Goat Yoga: I took a goat yoga class a few months ago where little goats and sheep hang out around you while you do stretches as a group. The animals were very cute and I think I enjoyed feeding/petting them more than the actual class itself.
 
Culture: In Paris, we went to the Louve (which was very crowded and overwhelming, but still lovely). In Cadaques, Spain, we visited Dali’s house and museum—which was incredible. Highly recommend visiting it if you’re ever in the area of Barcelona. The Nelson-Atkins Museum of Art in Kansas City also took me by surprise—it was excellent and is in my top five for favorite museums I’ve visited.

Work Travel, Life Travel

I traveled to two conferences this year: An IRCE pre-conference gathering hosted by BigCommerce in Chicago, and Content Jam (also in Chicago.) I’ve mentioned before that conferences are not really my jam, but the city is only a few hours away by train—so I went and checked these two out.
 
Brandon and I also did some recreational traveling throughout the year, with our biggest trip taking us to Paris and Barcelona in May—more on that trip here.

Other trips included:

• San Diego, CA

• Los Angeles, CA

• Louisville, KY

• St. Louis, MO

• Kansas City, MO

• Denver/Silverthorne/Colorado Springs, CO

In February, Brandon and I went out to California for a work conference he had in San Diego. We extended that trip a bit with a long weekend in LA where we met up with his brother, Josh.

Our time there was FUN: We made it to both Largo and UCB comedy clubs, ate incredible Korean food, visited a dog beach (!!!), had tasty lobster rolls, stayed at the Ace Hotel, visited The Getty—and those are just a few of the highlights.

Later in 2017, my brother, Brandon, and I drove out to Colorado. I had never been there before and was blown away with how beautiful it was.

A memorable moment was in Silverthorne when we drove up into the mountains where there was a stream running alongside the road. We stopped and parked by the pine trees for a while, enjoying the fresh air and the sound of the water. It. Was. Bliss.

Goals for the Year Ahead

I always struggle with this part. What do I want to accomplish in 2018? To be completely honest, I’m not quite sure yet.
 
I do know I want:
 
More Skype chats.

I made this a priority every month in 2017, and I got one-on-one time with lots of fellow writers that I now talk to on a regular basis. Plus, it helps keep me from getting too lonely and it’s nice to have a network of people I can refer work to as well.

More in-person meet-ups. 

I have a bad habit of staying in my hermit hole, but I always like it when I get out and meet up with people. This year I had coffee with my semi-local writer friend Courtney a few times, and a friend and I are meeting up in St. Louis in a few weeks for a mini-workcation.

More work-life balance.

This year I finally got to enjoy some of the perks of freelancing and gave myself permission to take a day off for things like hiking in the summer and the occasional mid-afternoon movie. I said no to a lot of opportunities, but in exchange, I wasn’t constantly worried about my to-do list. It was pretty great.
 
The rest is still kind of ??? for me. And I’m okay with that. This openness leaves room for new ideas and opportunities that pop up along the way.
 
Thanks for reading—I hope 2018 is your best year yet! 



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End-of-Summer Freelancing Reflection

Summer’s over.
 
Usually this makes me sad.
 
I think, “Where did the time go? I didn’t do all the things I wanted to do!”
 
But this summer, I feel like I finally got it right. I allowed myself to enjoy the flexibility of freelance writing.

• I took a few afternoons off to go swimming.

• I hiked. I kayaked. I took long walks with my dog.

• I traveled to Paris and Barcelona.

• I sat by a stream in the Rocky Mountains.

• I went to a movie by myself on a Friday afternoon and ate popcorn.

• I read lots of books in my hammock.

 And guess what?
 
I didn't earn less money. I didn’t lose any clients over it, and not a single deadline was missed. I still worked hard. I just worked fewer hours.

What I learned from better work-life balance

Because I was on a schedule with shifted priorities, the hours I did spend working were more focused, productive, and overall—more enjoyable.
 
I finally felt in control of my work.

It put me in the right place to jump into new opportunities:

• I worked with Paul Jarvis on his freelancing course (more on that soon.)

• I made my first YouTube video.

• I did a live writing tutorial with Joanna Wiebe over on Copyhackers.

And this was a really different feeling for me.

Over the past three years of freelancing, I kind of resented summer because I never let myself enjoy it.

I just kept working. And working. And working. And then, POOF! Summer was over. Buh-bye.

Now, summer is over again. But I'm not sad about it. Fall is here (I've got the window up in my office today and a sweatshirt on.)
 
If this is your favorite season (like it is mine) and you have the ability to set your own hours, my message to you is this:

Give yourself permission to enjoy it.

This article originally appeared in my newsletter, A Cup of Copy. Sign up and get these free tips sent right to your inbox every other Wednesday.