Reflecting on my 4th Year In Business: Top Highlights and Lessons Learned


Four years and one month  . . . this is how long I’ve been running my content marketing business. 

I’ve now been working for myself longer than any individual job I’ve ever had. 

When I went out on my own in November 2018, my goal was to build a sustainable business for the long haul. This goal remains unchanged. 

Here is a recap of some key highlights and lessons learned in year 4.

Seek out More adventures

I went into my fourth year in business with my 2022 theme of adventure. I wanted to dive in and experience new things – both in my business and personal life. (And the business actually grew by almost 10% YoY in the process!)

I was longing to get back more freedom of time and location that I sacrificed in the name of hard work to get the business off the ground in late 2018 and 2019. And then, because of the pandemic in 2020.  

In reality, this started with a move to Colorado at the end of 2021. 

It also meant that I did a fair amount of travel in 2022. In fact, there was an 11-week stretch in the fall where I was on a plane for either business or personal travel 10 out of 11 weeks. Maybe, I overdid it a bit?

Being over-reliant on async comms 

I’m a big fan of asynchronous communication. Tools like ZipMessage, Slack, Notion, and Trello make it easy to have nuanced conversations across timezones. However, at times this year, I leaned too heavily on async comms. Instead of saving time, it ended up creating issues that could have been avoided with a `20-minute phone or Zoom call.

Striking the right balance between when something can be handled async vs. when to get on a call is a skill. And it is a skill that isn’t taught to most entrepreneurs or remote workers.

In the past couple of months, I’ve course-corrected and added more live calls, particularly related to client onboarding and team check-ins, than I used to have. Even though it has introduced some new calendar / time management challenges, it has proven to be a smart decision. 

Learning from a failed productized service idea 

research service offering

One of my goals at the beginning of this year was to launch an additional, complementary revenue stream. So, I soft-launched a content research productized service.

While I did get one paying customer, it became apparent through many idea validation interviews that this was the definition of a vitamin product. If it were to take off, it would require a lot of education and marketing. While I still think there are legs behind this idea, it didn’t make sense to invest heavily in such a low cost offering. Ultimately, I decided to pause it to focus on going all-in on my three proven service offerings: content strategy, long form writing, and email copywriting.  

Building a tiny team

One of the areas that have been rockier is building out a small team to support the business.

It felt like my entire year was centered around should I hire, who should I hire, how much can I afford, and how to train them (when I was already slammed).

In reality, I’ve hired way too slowly and been too cautious for too long. It started to catch up with me in Q4 of this year when my VA quit, and I was on the road a lot. (More on that in the next section!)

Investing in myself

I went into this year knowing that if I wanted to take my business to the next level, I was going to need to up-level my skills and have some mindset shifts.

This meant I invested more this year into getting in the right rooms (largely in events and conferences) and coaching from people who have built what I’m trying to build.


CaboPress attendee photo

The largest investment I made this year was going to CaboPress in early October, and it was so worth it. 

CaboPress is an invite-only tiny conference of ~50 entrepreneurs at an all-inclusive retreat in Mexico. 🇲🇽

Despite hearing nothing but awesome things from a few former attendees that I trust,  it was scary to invest in this event.

  • 1.) It is the most money I’ve ever spent on a business event.
  • 2.) I had to get my business in a place where I could mostly not work for an entire week,  and deal with my fears that everything would burn to the ground if I did that. 

None of my fears happened, and I got so much out of this event. Two and half months later, it has already paid for itself 3x over.

I think that’s a testament to how Chris Lema runs this event. He’s a master event organizer and did some great things that really stuck out, including: 

  • 4:9 event format – The best insights and conversations at events typically happen during the “hallway track,” not in the actual talks. Chris understands that better than most. There were 4 hours of poolside talks in the morning followed by ~9 hours of conversations, which meant you could dive deeper into insights that you learned from earlier that day (or earlier in the week). 
  • All of the talks happened in the pool – At first, I thought this was just a gimmick. In reality, it is actually brilliant because it forces all of the talks to be conversational and experience-led. You can’t have Powerpoint slides when you are presenting in a pool. And the simple fact that all of the speakers were called “hosts” further reinforced this conversational approach. 
  • Curated lunch groups – We met with the small group each day for lunch (Waves at Bryan, Lisa, and Mateo!) to recap and dive deeper into any key insights from the morning’s poolside talks. I suppose this could be a disaster if your group didn’t see eye to eye. Fortunately, in my case, Chris nailed this pairing and learned so much from these informal lunch sessions.
  • It is about taking action, not taking notes – I used to judge conferences by the number of notes that I took. Now, I judge it based on the quality of action items. For instance, a few conversations at CaboPress are the reason why I decided to hire an operations coordinator instead of simply backfilling my VA.
operations coordinator job ad on Dynamite Jobs

Finally, it made me realize that small events are more impactful. I think there is an inverse relationship between the amount of value you get from a conference and the number of attendees. Maybe, it is the introvert in me but smaller events like CaboPress mean you can get to know and have deeper conversations with more attendees.  

Looking ahead to year 5

I’ll be sharing my theme for the year ahead and some upcoming goals next month.

About the author

Jessica Malnik

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