Reflecting on my 5th Year In Business: Top Highlights and Lessons Learned


1,825 days. 

Or, 5 years.

I’ve been running a business for 5 years now. That’s longer than any single individual job I’ve ever had. In fact, I have clients that I’ve been working with longer than any individual W-2 job I’ve ever had. 

This year was the weirdest year I’ve had in business full of as many – if not more – ups and downs as my first year in business.

  • I had my lowest sales quarter in three and half years. Then, the next quarter saw my highest revenue quarter I’ve ever had in business.
  • I also broke my monthly sales revenue record twice.
  • I also struggled with a couple of challenging situations that knocked my confidence more than they should. And that turned out to be a blessing in disguise and it forced me to level up my mindset. 
  • I spoke at a conference in Thailand. 
  • I got featured in The Wall Street Journal (WSJ) for the first time. Bucket list item.
  • I turned the mic over and my podcast editor, Sebastian, interviewed me for our 50th episode. 
  • There are now more than 60 episodes of The Remote Work Tribe podcast. This year, I interviewed some dream guests and the podcast was listened to in over 109 countries. 

But, I also realize that’s the reality I signed up for when I broke away from corporate employee life.

The ups and downs make this entrepreneurial journey, dare I say more fun. 

So here’s what I’ve been up to in my fifth year in business.

Breaking through a growth plateau 

I know without a doubt that I don’t want to build a small agency let alone a large one.  I’ve known this since year two. I’m quite content w/ designing a solopreneur business with a small team of badass independent contractors that delivers a delightful client experience and consistently impactful results.  

But, I recognize this structure has some inherent limitations and quality of life questions that I need to grapple with as I scale, especially as I don’t want to live to work. I want to build a cool business and not a prison where I have to work 70+ hour weeks to continue to hit new revenue and profit goals. 

The cliche founder advice is “to raise your prices.” However, with everyone raising their prices due to inflation over the last year, we’re probably bumping into a real ceiling. So, it is also about getting smarter about how to protect profit margins. 

Building a sustainable business 

I’ve said since year one that I want to build a business for the long haul. Something that could be around for decades.

A lot of the business owners I look up to the most are the ones who have been in the arena with the same business for 5, 10, or 20+ years. 

This means balancing the desire to grow sustainably year over year without losing motivation. 

This means that I spent a lot of time this year building and improving existing systems and processes.

For instance, one of the things that is helping is getting more disciplined with cash flow planning and cash flow (and sales pipeline) forecasting. This has also helped me get more clear on what my most profitable work is and how it intersects with the clients I work with best. 

Simplifying The services I offer

I made some tough decisions this fall after reflecting on my progress at a business retreat/conference in early October that led me to get really clear on the services that I offer moving forward in the business.

I started from first principles on all of the work that I’ve done in the last few years:

  • Where I get the best results for clients
  • What I actually like doing
  • What’s profitable
  • What I can create systems and processes around

This also meant making the hard and scary decision to part ways with one client that I adore but was no longer a great fit with this direction.

It also meant I’m in the process of refreshing the website and repositioning a few key services.  

Building out better sales and marketing systems 

Maybe it’s the cobbler’s shoes problem or the fact that I don’t like the idea of leaving 100% of sales to referrals and repeat clients. (I’m lucky and grateful that I do get a lot of repeat clients and referrals, but the idea of being solely reliant on something you can’t control has never sat well with me.)

It wasn’t until I found an inbound marketing channel that actually worked for me (and got good results) late last year that forced me to get more serious about a system that would make it consistent. (I even gave a talk about this at a conference.)

The next part was building out my sales systems and processes to capitalize on this. I’m still refining this, but it’s been the biggest internal project I’ve been working on in Q3 and Q4.

The end result is better processes for my business and for my clients. 

Lots of AI experiments

Truth be told, I’ve been experimenting with AI since the GPT-2 days. But since ChatGPT went live a year ago, I’ve really ramped up how I think about and use AI in the business.

I’m very pro-AI but not in the way a lot of people think. I don’t think AI is great for the actual writing but I think it is ideal for so many other marketing and administrative tasks. 

I even did a free workshop about how I’m using it back in September. 


In a few weeks, I’ll share what my theme for 2024 will be and some goals that I’m going to be tackling. 

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About the author

Jessica Malnik

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