As I enter my 3rd year in business, I’m going to share some of the key highlights and lessons learned on days 365 – 730. 

I started my business in November 2018.  

In my first year in business, I had some early wins. 

However, I got to that point through intense focus and working A LOT OF HOURS. It wasn’t a sustainable way to grow and run a business. 

Since day 1, my goal is to run a business for the long-haul (one that I could run for decades).

While I had aggressive revenue goals for year 2, I knew I couldn’t keep working at the pace that I was working at. 

I was at a crossroads.

  • Do I build out a full agency, focus my time on business development, and hire a team to fulfill the client work? 
  • Or, double down on “the solopreneur route” and impose strict limits on the number of clients I’m actively working with?

I chose the solopreneur route. More importantly, I love all of the clients that I am working with now. Plus, the systems and processes I put in place this year mean that it is easier to manage my workload and I’m producing even better results for clients consistently. 

Sidenote – I hesitate on whether or not to call myself a “solopreneur” and despise the term “freelancer” for two big reasons. 

  1. I think it implies a transactional mindset and that you somehow aren’t really committed to the clients you work with. That couldn’t be further from the truth for me. I actively choose to work with fewer clients at any given time, as I’d rather work with a client where I can get fully behind their business’s vision, help them grow, and work together for a long period of time instead of working on one-off projects or day rates.
  2. I think solopreneur makes it seem like you work in a silo and completely alone. (That’s not the case for me, as I do have a few folks who work with me on everything from marketing my business to research, administrative tasks, and the occasional “overflow work.”) And, I couldn’t do what I do without help. 

Mitigating risks

While this decision to stay a solopreneur was absolutely the right decision for me, I knew it was going to introduce more risks in my business.

While I still have a lot to figure out in this camp, I made two smart decisions back in December and January. 

Implemented The Profit First Method

For those unfamiliar with Profit First, it is basically a cash flow management system that helps you run a more profitable business.

Most business owners think about profit as an afterthought.  

The Profit First Method forces you to prioritize profit over expenses. 

The premise is pretty simple – you divide up your income each month into a series of 5 buckets  – income, profit, owner’s pay, tax, and operating expenses. You are supposed to transfer a fixed percentage of income that you receive twice a month into the corresponding accounts/buckets.

Now, I run a slightly modified version of this framework, but the premise still holds true as I’m in the habit of setting aside money each month for taxes, expenses, business savings, and personal savings. 

Given that just about 2 months after I set up this new cash flow management system, the entire world would shut down due to a global pandemic and recession. This might have been the best decision I made looking back. 

Launched a 2nd Site 

The other decision I made back in December of 2019 was to launch a 2nd site as a side project. The site came from scratching my own itch. I’ve been working remotely for 5 years, and I found myself on so many occasions having questions about particular nuances of remote work, whether it was around company culture, managing people remotely, handling a tricky interpersonal conflict, or just general comms. 

While there are plenty of amazing resources for how to find and land a remote job, I was frustrated by the sheer lack of resources available for how to manage teams remotely and build a thriving remote team culture.  

So, I created a site mockup and concept in December 2019. And, The Remote Work Tribe was born. 

Here is a screenshot from when I actually bought the domain and launched the site live in early January.

While it is still very early days, the long-term vision is for this site to become the go-to independent resource for remote managers (think anyone from an employee managing 1 direct report to a remote founder managing a team of 100+ employees).

For me personally, I have four goals with this site. 

  1. Scratch my own itch – after all, I launched this site as a way to help others, including myself.  
  2. It is a way for me to dogfood new ideas, systems, and processes on my own site before I introduce them to clients. 
  3. It quickly became another marketing channel for my business.  
  4. It is an additional (albeit small) revenue stream.   

Running my first business during a global recession and pandemic 

Like everyone who is under the age of 100, this is my first time living during a global pandemic. 

It is also my first time running a business in a recession. 

Admittedly, I still had some mild PTSD from the last recession, given that I graduated college and entered the workforce at the end of the last major recession in early 2010 when literally NO ONE was hiring entry-level employees.

It took me 6 months to find my first full-time job. And, my first “grown-up” job would ultimately teach me more about what I didn’t want to do than anything else. That’s another story.

So when the pandemic and recession first started, I panicked back in March and April. While I had a couple of small(ish) setbacks, this also gave me a chance to do some much-needed reflection. 

For example, I made a risky decision (at the time) in April. I carved out the time that I usually devoted towards business development each week and used it instead to continue to build out The Remote Work Tribe. 

Up until this point, I was working on the site – largely as a fun project on weekends. When the pandemic started and everyone – who could do so – started working from home, I felt like the opportunity for this site became a lot larger. 

Pro Tip: Here is some of my favorite content on The Remote Work Tribe.

Want to get the latest articles on managing remote teams straight to your inbox? Subscribe to my newsletter. 

Doubling down on masterminds   

At the end of last year, I made a plan to attend 6 conferences in 2020 as well as meeting up with as many clients – present and past – in-person as possible. 

While I am building a remote-first business, I saw firsthand the value of meeting up with clients in-person and attending conferences in 2019. 

I wanted to double down on that in 2020. 

I managed to meet up with 2 clients in-person as well as attend 1 conference back in March (that I combined with a mini-birthday vacation in San Diego) before the pandemic put those in-person plans on hold. 

While I can’t wait until it is safe to attend conferences again, instead of sitting back, I went all-in on masterminds. At the time I’m writing this, I’m currently in 3 small masterminds/accountability groups. Each one I’m in has less than 4 people (including myself).  

The 5 hours (or so) I spend each month that I spend in these masterminds have helped me stay productive, focused, and accountable in what is surely the craziest year most of us have ever seen. 

Plus, it has also been a great way to connect with fellow entrepreneurs on a deeper level as well as expose myself to new ideas. (While it is not the same, it is filling some of the voids left from not being able to meet up with groups of people in-person at larger dinners and events.) 

Looking ahead to Year 3 

When I first went out on my own in November 2018, I thought once I had worked with 10 clients, all of my big challenges would go away. 

It is okay to laugh at how naive I was.

I realized that the longer I’m in business, there will always be problems and challenges. They just evolve. 

Here are a few of the challenges that I need to work through.  

Getting better at saying “No” 

I’m naturally ambitious, optimistic, and a bit of a people pleaser.  While this trifecta definitely has many real advantages, it also means that I get easily excited by cool projects and hate letting other people down.  

Building more systems and processes in my business 

I came to the realization recently that I love designing systems and processes, but I am not always great at following the processes I create. I need to get better at this because processes are what allow me to streamline my work, delegate tasks more effectively, and deliver results consistently.    

Prioritizing my mental and physical health 

If there is one thing that living in the middle of a global pandemic has taught me is to prioritize living a healthier lifestyle. This means getting enough sleep, eating healthy, exercising, and practicing self-care, among other things. 


In December, I’ll share my post with my theme for 2021, along with some of my goals for year 3. 

About the author

Jessica Malnik

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