Self Employment: Year One Recap

I started my first business in high school, making websites for anyone who’d give me a shot. It was a great way to make money that I carried through college, grad school, and my adult life. I even did it full time a little after college, but lack of benefits and the need to learn more forced me to find a full time job. For pretty much that entire time, the stakes were different – and not very high. I didn’t have anyone except myself to support and I didn’t require too much.

That changed when I got married and had a daughter. I thought my chances at full time self-employment were dramatically lower as a result. However, today marks the anniversary of me leaving my full time job to pursue my side business full-time. I’d like to reflect on the first year.


Most drastically, I have a 15 month old instead of a 3 month old. She’s a lot more self sufficient and is sleeping through the night. We’re in a good routine and I’m grateful for that. I’m able to focus better, and though we don’t send her to daycare, I have a bit more freedom and I’m less distracted. There were some challenges though.

Babysitter trials and resisting daycare

My wife and I decided that we didn’t want to send Teresa to daycare and worked very hard to stick with that decision. There were a few trying times though – we lost a couple of babysitters due to other commitments or it not working out. We finally have 2 we’re happy with: one for the summer and date nights, and one for the school year.

Trying to do a 4 day week

During our babysitter woes, I tired dropping down to a 4 day work week. It worked for a short time, but ultimately wasn’t a good long term solution because I was falling behind on work and didn’t get an opportunity to make it up.

I still try to do that from time to time, but it’s not as regular, and I have a bit more control over when I do it.


OK – on to the business part. I was optimistic going out on my own because I had some measured success, as well as some work in the pipeline on day one. What I hadn’t accounted for was the added expenses, like buying new equipment. I realized too late that I would need to buy a new laptop, as my primary machine was my job’s. Since I was moving into video editing, I also needed something fairly powerful. Any income I thought would get me through the first part of the summer basically went towards “start up” expenses.

The Hard Parts

Aside from that, things got slow — the summer slump was in full swing. Then we had a bunch of personal expenses in July and ended up dipping into savings earlier than I hoped. Then I realized I had no idea how to run a product business.

Products are different from Services

The first lesson I learned was how different running a product business was from running a service business.

I had an easier time selling one $5000 website than 100 $50 courses

I realized I hadn’t built the audience I needed, and that products take time to build up. People need to be able to trust you when buying a product from you, and I didn’t earn enough of that yet…especially for the courses I was trying to sell.

I also realized that I didn’t understand my target audience — who they were or what they were trying to do. One year in and I’m much better at that.

Biting off more than I could chew

So I panicked. I reached out to a bunch of people trying to sell sponsored content without a real model (outside of my podcast). I took on freelance work and contract videos. I laid a lot of groundwork in July and August.

The problem is that all of that groundwork started to become fruitful around the same time. So I started to miss deadlines and not deliver on promises. And I let the things I needed to do for my business slip.

These were the bad parts and honestly, they all happened around the same time, in the first 5 months. After one very important event, things started to get a lot better.


I wrote about this shortly after I attended, but going to CaboPress was the best thing that I could have done for my business. I learned a ton from a lot of very smart people. The big takeaways were:

  • Understand User Intent
  • Increase Engagement with my audience
  • Build more trust through good content
  • Implement basic e-commerce strategies (like cart recovery)

I started these immediately after I got back in October and I’ve seen a great impact.

The Great Parts

After learning a ton from CaboPress, my product business is on the up and up. I have a clear message and a plan. I’m learning more about my audience and what they want, and I’m doing contract work that makes sense in the scope of what I’m currently working on. I plan to be mostly product-driven by this time next year.

Tools that help

There are a few tools that are helping me a long the way. By and large, Convert Kit has been the most helpful. I’ve been able to better segment my lists, do more targeted marketing so I’m not bombarding people with nonsense, and most important, I understand my users’ actions better.

There are also 2 e-commerce tools that have been great: Metorik and Jilt. Metorik helps me get good stats / analytics on my shop, and Jilt focuses on cart abandonment.

My Mastermind Group

My mastermind group has also been hugely helpful. Before CaboPress, one of my friends asked what I’m known for, and what exactly I do. I’ve never been able to answer that question well. So I decided to really think about that, and take the answer to Cabo. It helped frame the whole week for me. As a result, I was able to get more out of the event.

Meeting every other week with the group also helps keep me on track. Just recently I was struggling to complete (or even start) a project that I had gotten paid for several months prior. One of the group members told me that I should finish the project that week or refund the money. I said I’d finish it by Friday, and he checked on me at the end of the week to make sure. I did, and it lead to more work.

Just having a group of folks to bounce ideas off of has been great. I’m not working in a silo and I can better vet ideas before I start doing real work on them.

Overall Success

Overall, I would call this first year a success. I’m not so open as to share my numbers, but I have more than doubled my course revenue from all of 2017 and I’ve landed a few great strategic partnerships.

I’ve also been able to grow podcast revenue by adding a mid-roll spot, and maxing out the spots per episode at 3 (up from 2).

Plans for the Next Year

Now that I feel more comfortable in what I’m doing, I have some big plans for June 2018 – June 2019. This biggest of those plans is to roll out memberships on Creator Courses.

Creator Courses

I’m 1-2 courses away from having enough value to add the membership portion, and want to do it by the end of the summer. This will allow me to deliver great value to current and potential customers, build a better community, and have a more predictable revenue money year over year.

On that same token, I’d like to keep adding the my Course catalog. My goal is a new course each quarter, while also keeping the existing courses up to date.

Finally, I’m working out clearer plans to license my courses to freelancers and agencies, as well as develop custom training that builds on my current course lineup.

The Podcast

I’m incredibly happy with my podcast’s growth over the last year. I’ll do a more in-depth write up when the show turns 2 in August, but this year has seen a 30% increase in downloads. I have 2 areas where I’d like to grow.

The first is audience engagement. I want to connect to my audience more and deliver value for them. I’m adding behind the scenes stuff on instagram and doing a better job of building the Facebook community. I believe this will also help me grow my presence on Patreon. I cover that in the latest episode.

I also want to deliver more value for my sponsors. 2 years in and I’m grateful for those who believed in me and helped me get my start. I’m committed to making sure they feel they are getting a good return on their investment.

Here’s to Year Two!

I’m excited to continue growing the business (and as an individual). This has been a huge learning experience for me, and I’ve been having a lot of fun growing in an area that I’m new to, despite my 15 years of freelance experience.

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