Reflections on my first year as a company of one

Note: This was originally published in my newsletter, Leading Thoughts.

We grow as a society by sharing our successes and failures. So in this special issue of Leading Thoughts, I’m pulling back the proverbial curtain to reveal how 2022 really went.

Biggest wins

I built a strong inbound engine.

One thing you should know about me: this isn’t my first rodeo. In 2011, I quit my magazine editor job to move to Europe and freelance. I made money by sending cold pitches and applying to gigs. And by “made money,” I mean “earned a few hundred dollars here and there.”

Eventually, I admitted that I lacked high-value expertise and business acumen. So I went back to work to upskill. I spent the next seven years building and leading content teams while obsessively learning all I could about marketing and business operations.

By the time I quit my marketing director job on January 26, 2022, I had the skill set, resume, network, and reputation I needed to operate my business at the next level. Because I put in the work before quitting, I had a steady stream of inbound hand raiser leads. (On day one, I already had $145k in bookings.)

I found a community of peers.

Several people asked me what resources helped me grow. At this stage of my career, I know enough about content marketing to make my clients money. I won’t grow my business by learning more about content marketing; I’ll grow by learning to optimize my existing offers and systems.

Surprisingly, the most helpful resource has been building a supportive community of peers—people who are roughly where I’m at in terms of experience and income. (Some are a step ahead, and some are a step behind.)

Three female solopreneur friends and I started a monthly mastermind where we share wins and learnings. I walk away from every call with a new idea or template I can use to work more efficiently.

My kids are happy and healthy.

My daughter turned six, and my son turned eight. It wasn’t an easy year (my daughter had two surgeries in 2022), but she’s doing great, and we all survived. Hooray! We made time for four family vacations—NYC; Seattle, WA and Portland, OR); Old Orchard Beach, ME and Portland, ME; Lisbon, Portugal and Armação de Pêra, Portugal.

I sold more retainers than one-off projects.

Since 2011, my offers have evolved from one-off articles to one-off projects to hourly retainers to premium retainers. (A premium retainer is one where the client isn’t just paying for your time; they’re paying for the outcomes you deliver and ongoing access to you.)

In 2022, premium retainers made up 76% of my client engagements. I supplemented those with projects (research reports, case studies, and LinkedIn workshops).

Side note: I don’t work with more than three clients at a time. Most quarters, I have two ongoing retainers and one or two projects.

I nailed my positioning.

At the start of 2022, an Albatross hung from my neck and caused me more pain than a ‘90s choker necklace: I couldn’t succinctly explain my business. I didn’t offer one type of content or a productized service. Instead, I built custom proposals based on client needs; I helped with everything from hiring full-time content writers to creating content strategies to building processes to writing website copy.

I struggled to summarize my services on discovery calls. Sometimes it felt like I was talking in circles.

Then one day, I was on the phone with my friend Shannon when the words came tumbling out of my mouth: “I help sales-led B2B SaaS startups that sell complex, enterprise-ready solutions build revenue-generating content engines in 6-12 months. I do that by helping across four areas: people, process, strategy, and execution.”

How do I know I “nailed” it? Discovery calls went smoother (I could actually see prospects nodding and leaning in as I talked about how I help). And I’ve gotten positive feedback on my new website messaging. People fill out my contact form with messages like, “I need help with all the bullets listed on your home page.”

I optimized my proposals.

Over the years, I wasted LOTS of time sending proposals to poor-fit clients. Total waste of time. I got so discouraged at one point that I stopped sending proposals altogether.

Eventually, I started sending ‘em again … with hit-or-miss results. Then I discovered Jonathan Stark’s proposal template; the clouds parted, and rainbow sprinkles rained down from the heavens. 🌈 By taking a new approach to proposal writing, I increased my close rate to 100%. (I shared my journey with Jonathan on his podcast Ditching Hourly if you’re interested.)

Side note: I’ve since iterated on Jonathan’s proposal template and made it my own. I’m thinking of sharing my process for proposal writing. If you’re interested in this, let me know!

 

I went back to the gym!

20-something Erin was a gym rat. I had a personal trainer, I did CrossFit, and I never left home without a cooler filled with “delicious” treats like tuna fish mixed with diced apples. But pregnancy, then two kids under two—and a son who didn’t sleep through the night for 2.5 years—took a toll on me. Once I got out of the gym habit, I couldn’t find my way back in.

After nine years of sitting on my lard ass, I went back to the gym in mid-2022. I booked two training sessions a week with a bodybuilder named Frank, and I allowed myself to work out in the middle of the workday when my energy levels were at their highest.

Even when I wasn’t motivated to go (which, let’s be honest, was all the time), I had to go because Frank was waiting for me. Having an accountability buddy is worth every penny.

I started a podcast.

In 2022, I published nine episodes of The Notorious Thought Leader. According to Listen Notes, it’s a top 10% podcast (meaning it’s in the top 10% of all global podcasts in terms of popularity).

I don’t know how long I’ll host my podcast (it takes a lot out of me), but I’ll keep going as long as I’m having fun. It’s a total passion project.

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Biggest regrets

I didn’t carve out enough time to work on my business.

Like a big ol’ dummy, I booked 40 hours of client work in Q1 without leaving space for running my business. You know, things like marketing, networking, invoicing, emailing back and forth with my accountant and payroll vendor …

Turns out, I needed at least 10 hours a week to work on, not in, my business. Who knew? 😉

 

I didn’t get organized BEFORE I quit my day job.

Since I had a full workload waiting for me on day one of self-employment, I never had space and time to do foundational work like drafting SOPs (standard operating procedures), writing canned email responses, and building slide decks to explain processes to new clients.

Since I didn’t prepare, I found myself doing these things on the fly in my moment of need—adding more work to my already overflowing plate.

 

I said yes when I should have said no.

Research reports are my only productized service: I offer a bronze package (writing only), a silver package (strategy and writing), and a gold package (strategy, writing, and project oversight/advising).

In Q1, a client purchased the bronze package. Then, after the project kicked off, they asked to upgrade to the gold package. I didn’t have any wiggle room in my schedule (see above), but I said yes anyway. The same client later asked me to help with a separate project, and again I said, “sure!”

Saying yes meant setting my alarm for 4 a.m. multiple times so I could wake up before the kids and get the extra work done. Talk about stressful. The extra money wasn’t worth it.

I wasted money on business coaching.

Remember my albatross problem? I found the perfect solution (or so I thought): a business coaching program for solo consultants. On my discovery call, the co-founder told me they help people like me with problems like mine. Great, I thought, take all my money!

While my coach was a wonderful person, the program’s rigid productized model meant I had to sit through lessons on marketing and landing clients. I also suffered through group coaching calls I could have run myself. And the kicker? I never got clarity on how to position my business.

In hindsight, I should have vetted the program more thoroughly and explored other options. C’est la vie.

Biggest learnings

I don’t want to be a fractional head of content.

One of my first retainers in 2022 was a Fractional Head of Content gig with a fast-growing B2B SaaS company in the sales tech space. Great product, great people. But I was on 10+ calls a week, making me feel like I still had a jobby job. Moving forward, I stayed away from this type of engagement.

I love being a company of one.

Before going out on my own, I spent seven years leading large teams. No matter what was going on in my life, I put my problems aside and brought my full energy to work. But eventually, I burnt out.

As a company of one, I plan two no call days every week where I do deep work and feed my introverted side. And when I do have client calls (or podcast recordings or coffee chats), I show up feeling energized.

The ability to earn unlimited income can be a trap.

Someone asked me how I decide when to say yes and when to say no. 

At the start of 2022, I set out to replace my salary. After I quickly hit that goal, I moved the goalpost to (an arbitrary) $300k. But when I found myself burning the candle at both ends, I pondered the question: What good is money if you’re too tired to enjoy it?

The ability to earn unlimited income is intoxicating, but it can become dangerous if you don’t set boundaries. Going forward, I assessed new opportunities by asking myself questions like:

  • Do I really want to work with this person/company?
  • Am I saying yes because I want to hit some arbitrary revenue number?
  • Should I say no and spend that time building more passive income streams?
  • Should I say no and spend that time doing things that feed my soul?

 

Saying no to client work creates time to improve efficiency and build passive income streams. Sometimes you earn more by saying no to client work.

 

I learned to run an actual business.

In January of 2022, I graduated from 1099 freelance employee to legit business owner by setting up my business as an LLC (taxed as an S-Corp). So. Much. Paperwork. Luckily, I have a fantastic accountant and a payroll vendor who make everything a million times easier. I can’t imagine doing this alone.

Speaking of doing this alone, I hired a freelance web developer to help me with miscellaneous technical tasks that pop up a few times a month. At the risk of sounding hyperbolic, it’s been life-changing. No more dealing with customer service reps and trying to solve technical issues.

If you only take one thing away from this post, let it be this: outsource things outside your genius zone.

 

Overall performance

I made more money in 2022 than I ever had before. More importantly, I learned that money isn’t everything. 

Here’s the breakdown of my revenue sources in 2022:

Looking ahead

2022 was all about working out the kinks and trying new things. It was a solid first year, and I’m grateful. Can’t wait to see how 2023 shakes out. (I have a pretty big surprise up my sleeve!)

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