Reflecting on my 3rd Year In Business: Top Highlights and Lessons Learned


I’ve now been in business for myself for over 1,100 days. As I enter my 4th year in business, I’m going to share some of the key highlights and lessons learned from my 3rd year in business.

Since day 1 when I went out on my own in November 2018, my goal is to build a business for the long haul. Now in my 4th year, that mission remains the same.

2021 business revenue

In my first year in business, I was obsessed with hitting $100k in annual revenue. I actually managed to nearly double “my salary” from my last job but I was working all the time. It wasn’t remotely sustainable. 

So, in year 2, I found myself at a crossroads. 

  • Do I build an agency? 
  • Or, double down on “the solopreneur route” and impose stricter limits on how much I’m working? 

I chose the solopreneur route. 

Sidenote: I still struggle with the term, solopreneur, though, since it can imply that you work 100% solo all the time. That’s not the case for me, as I have a tiny team that helps with a variety of tasks each month. I couldn’t do what I do without all of their help. 

This year, I really focused on consistency – showing up day in and day out. I managed to grow my business 20% year over year in the process. 🎉

Now entering my 4th year in business, I can confidently say I made the right decision based on my business and personal goals.  

Creating more business systems and processes 

One of the critical elements of running a sustainable business for the long haul is having solid and repeatable systems and processes. While I love building systems, I’ve historically not been the best at following them. 

The catalyst that finally forced me to implement and stick to it this time was the one-two punch of the freak Texas Winter Storm in February 2021 (You learn real quick how disruptive a week of sub-freezing temperatures without electricity, heat, and running water in your home can be to all aspects of your business and life!) and getting dangerously close to burnout in March and April 2021. 

Sidenote: I also learned that weather-proofing is definitely not a thing here. My living room was 33 degrees indoors. 

33 degrees indoors

So, I evacuated to a hotel to avoid getting hypothermia in my living room (No exaggeration!). Here is a view from downtown Austin two days into snow and icemageddon. That “barely plowed” road is actually I-35 😰 

snowy I-35

Revamping my client onboarding process 

While I created and updated processes throughout the entire business to add resiliency and slack (think better documentation, not doing rush jobs, deadline padding, etc), the place where it had the biggest impact to date was in my new client onboarding process.

In May 2021, I had the uncomfortable realization that I was spending the same amount of time onboarding all clients. In more than a few cases, I actually spent more time onboarding a low-dollar, one-off project client than ongoing content strategy retainer clients, which is obviously problematic. 

This started by mapping out my process in Miro for my main service offerings (That’s content strategy, content writing, and email copywriting). 

Then, I started to turn these process boards into either a dedicated Google Docs or landing page. Here is the behind-the-scenes lo-fi mockup that I made for the content writing page.

miro mockup of my content writing process page

At the same time, I also streamlined my new client onboarding questionnaire templates.  

content brief questionnaire airtable form

Going back to the content writing example above, I turned my content brief template into a questionnaire (see screenshot!) that takes my clients less time to fill out (than writing a content brief from scratch!) and also greatly reduces the back-and-forth editing process. 

Not to mention, if a client doesn’t want to fill out the questionnaire, I include a direct link to my ZipMessage mailbox so they can record their answers instead.  It is a win-win.

The result of revamping these processes is that I got a lot better at identifying my right-fit clients and I also gained more confidence in my abilities.  

Note: For content strategy clients, after I send a separate onboarding questionnaire I schedule a short kick-off call. This entire process is templated. So, instead of having to reinvent the wheel each time, I’m just adding a couple of personalized details in my Airtable onboarding questionnaire template and personalizing the scheduling link via SavvyCal. (i.e. name, event title, url, etc)

personalized links

Meeting up with a few clients in-person again after 15+ months 

I run a 100% remote-first business. This doesn’t mean that I don’t ever meet with clients in-person. In fact, I met up with a lot of clients IRL in 2019. 

I didn’t realize how much I would miss that until a year into a global pandemic. 

So, being able to layer in some in-person work time with three of my clients as well as one of my freelancers that I work closely with after 15+ months of none of that during the pandemic was awesome. 

Investing in the business  

One of my goals that I set for myself earlier this year was to spend 10% of my time on marketing the business and on side projects. Most notably – The Remote Work Tribe – my media company that I launched in December 2019 centering around helping founders, CEOs, and marketers lead remote-first teams.  

At the very beginning of 2021, I launched a 2nd newsletter specifically for that audience. It is now larger than the newsletter that I’ve been running for 3+ years. 

Pro Tip: Interested in getting curated remote-first leadership resources in your inbox 1-2 per month? Subscribe here.

The other big RWT development was launching my first podcast over the summer. This has been something that I’ve wanted to do for ages. 

podcast process in Miro

You can find The Remote Work Tribe Podcast on Apple Podcasts, Google Podcasts, Stitcher, Spotify, and all of the usual places. 

Remote Work Tribe podcast episode

Looking ahead to year 4

Next month, I’ll share my post with my theme for 2022 along with some of my goals for year 4. 

About the author

Jessica Malnik

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