15 min read

It’s safe to say that we’ll all remember 2020.

There are a lot of reasons that we’ll look back on 2020 and cringe. As of this writing, we’re still in the middle of a global pandemic that the United States seems to have just given up on.

We’re in seeing a renewed fight for social justice, with more of us fighting against centuries of racial inequality than ever before.

The first two quarters of 2020 have taken an emotional toll on me just like they probably have on you. Everyone is hurting – individuals and business owners included.

But for the last two years, I’ve written an annual reflection on my own business.

To be honest, the anniversary snuck up on me this year!

But I wanted to go a little deeper on this year’s reflection. I wanted to bring you some real numbers, some behind-the-scenes, and the lessons learned.

And it’s important to note – I do not equate earnings with success. I certainly don’t equate them with happiness. If you look at earnings alone, my 2019 would look like a huge step backwards. But in reality, I believe 2019 to be far more impactful than 2018.

I’m optimizing for flexibility, fulfillment, and long-term vision. So as you’ll see in my 2019 breakdown, I accepted a short-term earnings compromise to get there.

If you want the tl;dr version, here’s a visual overview of my P&L every year from 2017. It includes the my actual figures for January through June of 2020, as well as a projection for the full year based upon those numbers.

If you’re ready to dig into what happened each of those years and why those trends look the way they do, let’s get started.

Year One: 2017

I spent the first four months of 2017 gainfully employed! Those earnings are not reflected in the numbers above or below, but it does mean that I had four fewer months to work with.

I quit my job in late April 2017. It came about a month sooner than I anticipated, but the timing seemed right for both me and the company I was leaving.

You can read more detail about that decision here, but it was a pretty half-baked move, truth be told.

I didn’t really have much of a plan, and I don’t recommend jumping into the deep end like I did!

The biggest victory was getting my first 15-member paid cohort of the Unreal Collective Accelerator off the ground.

Here’s my cringe-worthy first promotional video for Unreal Collective:

Pulling that first cohort together wasn’t easy. I ran a beta group of five members for a couple of months prior, and I was able to turn their stories into testimonials.

But I was still coming in with very little credibility.

The model behind the Unreal Collective Accelerator is pretty straightforward, and it’s similar to a typical mastermind program.

You take a small number of great people with ambitious goals, you force them into meeting once per week, and magic happens. Progress is made, goals are met, transformation is experienced.

Getting the right number of people, who mesh together well, ready to start the program at the same time is where you find the challenge.

But I’ve always been good at logistics and timelines, so I’m able to make it work – even if it was through brute force of a lot of conversations.

I wasn’t even calling it an accelerator at the time! I wasn’t sure what it was going to be – I thought it might be a live events company.

After that first program ended, it was October. And I realized I wasn’t going to be able to pull another group together before the end of the year due to Thanksgiving, Christmas, and the new year.

So my financial engine was put on pause until 2018.

And I was broke.

To scrape by, I picked up a couple of freelance gigs building simple WordPress websites, writing email sequences, and helping a friend launch his podcast.

Then in late December, I got a surprise email: an opportunity to become a LinkedIn Learning instructor. I walked through the application process and was accepted shortly thereafter.

Lessons Learned

  • 👍  Creating a budget was absolutely critical
  • 👍  Investing in mentorship and my own education was well worth it
  • 👍  When I’m in a bind, I look for work from the people close to me
  • 👎  I need to learn how to predict my cash flow
  • 👎  Things take longer to get started than I expect
  • 👎  When I underprice myself, it’s problematic through the project and for months afterward

By the Numbers

  • Gross income: $29,468
  • Expenses: $18,289
  • Net income: $11,179

Year Two: 2018

The start of the new year couldn’t come soon enough. When the year began, I was still working on a freelance marketing contract that saved my butt at the end of 2017.

But I wanted to start a new cohort of the Unreal Collective Accelerator.

And actually, 2018 was the first time I started calling it an Accelerator. I put a lot of thought into Unreal Collective as a business, because I wanted it to be a brand that meant more than just the 12-week program.

In February, I pulled my thoughts together and decided Unreal would split into three core product offerings:

  1. The 12-week program (Unreal Collective Accelerator)
  2. A community membership (Unreal Collective)
  3. Digital products and courses (called Guides at the time)

I broke it all down in this 24-minute monologue called “Unreal Collective 2.0” that I shared with the community (then about 35 people):

To start the year, I brought together another cohort of 15 people. At the same time, I began writing my first LinkedIn Learning course and even accepted a part-time Entrepreneur In Residence position with Columbus’s Smart City team.

So things got off to a strong start.

But I burned myself out. Outside of my business, I was:

  • Serving as Entrepreneur in Residence for Smart Columbus
  • Helping organize a track of events for Columbus Startup Week
  • Organizing a hackathon for Smart Columbus
  • Serving as Vice Chair of a nonprofit organization
  • Organizing a 6-month outdoor music series

…and most of that was a volunteer effort.

The Smart Columbus role was fantastic – I was able to make an impact for the team and we put on an incredible event.

And somehow I also wrote 4 courses for LinkedIn Learning, ran two cohorts of the Unreal Collective Accelerator, and launched our podcast, upside.

You can read my full 2018 reflection here

It was a strong year of earnings, but I really wanted to focus and devote more time to my core business. So I stepped away from the Smart Columbus role, the Vice Chair role, and the music series.

Lessons Learned

  • 👍  Creating LinkedIn courses were great for cash flow and creating my own content
  • 👍  Coaching others was a viable service that people benefitted from
  • 👍  Freelance work can pay pretty well
  • 👍  I can pick up freelance work pretty easily
  • 👎  Freelancing can also be a diversion from my core business goals
  • 👎  Volunteering a lot of my time was hurting my business
  • 👎  Earning more doesn’t matter if my costs increase
  • 👎  Earning close to my previous salary doesn’t matter if I’m saving far less

By the Numbers

  • Gross income: $72,713 (147% increase)
  • Expenses: $45,834 (151% increase)
  • Net income: $26,879 (140% increase)

Year Three: 2019

In 2019, I resolved to do less so that I could do more. I wrote in January 2019:

This year is all about doing fewer so that I can do more. Fewer projects, fewer opportunities that are outside of my core intention, in order to do more with the things I am focusing on.

It’s not unlikely that I actually earn less this year than I did last year. A large part of my income in 2018 was from contracting and ad hoc projects, and those take time away from building my core business.

Turns out, I was right. My income dropped 25% percent in 2019.

I decided to take on less freelance work – including courses from LinkedIn.

Instead, I focused on more Unreal Collective Accelerator cohorts and developing my own proprietary content.

That content took a few forms:

  • Freelancing School courses
  • More episodes of upside
  • Planning for the launch of a new podcast (Creative Elements)
  • My weekly newsletter, Work In Progress

I spent most of the first six months of 2019 producing the three courses within Freelancing School. It was a massive effort and the courses get really great reviews from students.

And all the while, I facilitated three sessions of the Unreal Collective Accelerator – welcoming 50 new members across three cohorts.

…and that was exhausting. The program itself is 12 weeks long with about 4 weeks of marketing and onboarding required up front.

Some quick math will show you that 16 weeks across 3 sessions equals 48 weeks out of the year…and I wanted to finish before Thanksgiving!

I ended up staggering the second and third cohorts a bit, with two sessions overlapping for two weeks. And it was intense.

But, at the same time, my courses were published and beginning to sell.

Our podcast, upside, even earned more than $20,000 in gross income through sponsorships and partnerships (not reflected in the numbers below).

Over the summer, that podcast business produced a full-length documentary about the startup ecosystem in Columbus, Ohio, called Test City, USA.

The film is 94 minutes long, features prominent voices in Columbus’s tech scene, and was shot beautifully.

Mallory and I at the Test City, USA Premiere

We spent the entire summer filming and editing, and due to some lucky timing, we premiered the film at the Film Festival of Columbus in September where it won Best Ohio Feature. It was also accepted into the Columbus International Film Festival in April 2020.

I don’t know if I’ll ever produce another film in my life, but I’m so glad that Test City, USA exists. You can watch it here.

To finish out the year, I created another course for LinkedIn Learning and signed an agreement with the Podglomerate, the network that I’ve partnered with for Creative Elements.

So while my overall income took a hit, I really put a lot of pieces in place to begin to build a larger, more scalable business through content and digital products.

And by cutting expenses, my net income was still up 24% from the year before! After a 2018 where I saved very little, I was able to dedicate money consistently to savings and retirement in 2019 as well.

Lessons Learned

  • 👍  There is power in focus
  • 👍  It’s worth living cheaply while I still can to develop a strong foundation
  • 👍  Thinking long term may require short term sacrifices
  • 👍  Plan your schedule ahead of time (programs, deadlines, product launches, editorial planning)
  • 👍  Direct outreach and relationship building is underrated
  • 👍  Forming partnerships can provide huge leverage
  • 👍  Let go of what is no longer serving you
  • 👎  Three cohorts of the Unreal Collective Accelerator is too many
  • 👎  A great product is useless without distribution
  • 👎  If you don’t help other people, your business is toast

You can read my full 2019 reflection here

By the Numbers

  • Gross income: $54,547 (25% decrease)
  • Expenses: $21,319 (53% decrease)
  • Net income: $33,228 (24% increase)

Year Four: 2020

We’ve finally come to 2020. After a year of declining income, I wouldn’t blame you if you expected this year was off to a rough start.

But fortunately for me, it’s been the opposite.

When I started my business more than three years ago, I intentionally designed it to be location independent. That was a lifestyle decision – I wanted to be able to operate my business from any location at any time.

That’s been a huge asset in the time of COVID-19. I’ve been fortunate that my business has not experienced any disruption.

I began the year with my typical cohort of the Unreal Collective Accelerator. But because I was a little burned out from the year before, I kept it small. I worked with two groups, one of which was almost entirely alumni of the program.

Unreal Collective Spring 2020

I find myself taking almost the opposite stance from 2019.

Running three cohorts of the accelerator was exhausting – and proved itself to be less economically attractive than freelancing work.

Not only does running a cohort take a lot of time to pull off, but it requires a ton of emotional energy.

I have to show up to every call and be positive, upbeat, and helpful. Every call, every week, without exception.

I love the Accelerator, and it’s not going anywhere. But I decided this year that I would prefer to take on some freelance work to both earn more and conserve my creative, emotional energy

Plus freelancing keeps me close to my customers – by continuing to freelance, I can create relevant content and guidance for other freelancers.

Things are just much easier going in to year four because I’ve already built so many systems:

  • I know how to efficiently spin up a cohort of the Accelerator
  • I have systems for managing my finances and my business
  • I have an Airtable system for partnerships and editorial planning
  • I know how to efficiently produce podcast and weekly articles

Plus I have an infinitely scalable set of products with my Freelancing School courses.

So I’ve been able to build relationships and take on some really great freelance projects to start the year, two courses with LinkedIn Learning, two Unreal Collective Accelerator cohorts, and selling my own courses.

Partnerships are ramping up. I’m appearing as a guest on more podcasts than before, contributing guest articles, and have my courses on the new Teachable Discover platform.

I’m creating more content than ever before.

Creative Elements debuted on March 24 and has been featured on Apple Podcasts, Stitcher, Pocket Casts, Castro, and Castbox.

And the show has more than 50,000 downloads.

Creative Elements downloads

I launched a LinkedIn newsletter in February, which will cross 10,000 subscribers this week.

And all the while, I’ve learned a ton about Search Engine Optimization and am focused on writing more articles for Freelancing School to capture organic traffic.

Six months into 2020, I’ve already surpassed my 2019 earnings and am projects to more than double them. Numbers below for year to date, as well as projections.

And I’m actually spending less time working. I’ve learned a lot from my partner Mallory, and I’ve gotten better and better at protecting nights and weekend time.

Lessons Learned

  • 👍  Managing my energy is as important as managing my time
  • 👍  Partnerships and distribution drive growth
  • 👍  Create content with the intention of capturing organic search traffic
  • 👍  Podcast guests are more accessible than you think
  • 👍  Listeners notice (and appreciate) high production quality
  • 👍  I love making podcasts
  • 👍  Investing in your business (time and money) pays dividends
  • 👎  Selling digital products is very hard – it’s hard to know where the funnel is failing
  • 👎  Having multiple weekly publishing commitments is a lot – add ongoing commitments slowly and intentionally

Numbers (year to date)

  • Gross income: $60,964 (69% increase over same period 2019)
  • Expenses: $13,624 (1% increase over same period 2019)
  • Net income: $47,340 (110% increase over same period 2019)

Numbers (projected 12 months)

  • Gross income: $120,928 (124% increase)
  • Expenses: $27,248 (28% increase)
  • Net income: $94,680 (185% increase)


Investing my time and energy into my own business has been a critical move over the last 12-18 months.

While I know my 2019 revenue numbers look like a step back, I knew it was a short-term sacrifice for a long-term vision.

And now with a much stronger foundation underneath me, I’m doubling down my efforts on Freelancing School, Unreal Collective, and Creative Elements.

I will continue to strengthen my foundation, and creating free content that is useful and widely accessible is one of the biggest pieces of the puzzle.

That means I may fall short of those final 2020 revenue projections. And I expect my expenses to grow a little bit as well due to hiring a couple of virtual assistants and investing in marketing.

But it truly feels like I am building my business and not just increasing my earnings.

The vision of Unreal Collective 2.0 that I shared in the YouTube presentation from 2018 has actually now been realized. I continue to run the accelerator, and I have digital products (although under the brand Freelancing School).

And right now, I’m making membership into the community more accessible than ever before.

The Unreal Collective community is my favorite place to spend time online. We have ~110 members strong in our community Slack channel, and it is the most manageable, friendly, and personal Slack group I am a part of.

If you want to join a generous, uplifting community of creatives and business owners, you can now join us for just $99 per year.

To protect the community we’ve built and to make sure it’s a great fit for you and everyone involved, there is a short application to join.

Click here to learn more and apply to join us

We’d love to help you along YOUR entrepreneurial journey too.

Thanks for reading, and I hope to share an even bigger update with you next year.

PS: I work individually with a small number of coaching clients. If you’re interested in working together, send me an email.

PPS: If you want to follow along as I head into year four, subscribe below