Solopreneurship — 3 years later.

I am consistently asked to have coffee (nowadays, it’s calls and Zooms) with people who are thinking about starting their own thing. They want to go solo, fly free, run their own show. Sometimes they are interested in focusing on Design Sprints, but often they are interested in something adjacent: digital strategy, digital transformation, product leadership, brand strategy, etc.

As a natural-born helper and a firm believer in the power of business karma, I say yes most of the time. The thing is, I’m feeling like I have less and less time these days so I’m saying no to many of these requests and referring people to this article instead!

This is our family after about 40 days in quarantine. Photo by Zoe Prinds

The ask:

After 50+ coffees and conversations, I’ve determined that there’s a pretty common set of questions that people want me to answer.

They want to know:

  • How did you do it?
  • What have you learned along the way?
  • What can you tell me that might help me on my journey?
  • Should I quit my job too??!

The story:

I quit an amazing job so that I could work in alignment with my values.
I quit my job working as a strategist at a digital product studio called GoKart Labs. I worked with people I adored and was never bored but I quit because I wanted to have 100% control over what I said yes and no to. I believe that we are what we make in the world. Our legacy is our energy, actions, and creations. We are all contributing to and creating our future with every action or inaction we choose. I wanted to be able to work on the types of problems and products that I believe in. The only way I could gain this autonomy was to be the boss. So I quit.

I focused on Design Sprints because they’re incredibly effective.
I started running sprints at GoKart Labs after reading the Sprint Book and saw how well they worked. A Design Sprint is a collaborative design effort that brings a team together over a series of 5 days to clarify the problem they are solving, create solutions, build a testable prototype and test it with real people. It embodies many of the principles of Human-Centered Design but is a much less ambiguous process. It’s designed to get the team to a testable concept so that they can learn whether or not to invest in an idea. Anyone who’s ever worked with me knows I like to cut through the BS and get to clarity more than anything. The Design Sprint does that.

My hunch: Design Sprints will continue to gain traction.
I saw that my clients on the coasts were familiar with Design Sprints, but they weren’t yet a part of common nomenclature in Minneapolis. “It’s only a matter of time,” I thought. I figured that like Human-Centered Design, the Design Sprint would gradually be adopted by more and more organizations. I wanted to not only run sprints, but also teach others how to use Design Sprints to move quickly to make decisions, prototype, test, and learn.

Process = Impact
I am a bit of a process and opps geek. I loved both the process of setting a team up for a Sprint and facilitating the Sprints themselves. This is an important detail because if you go out on your own there’s most likely going to be a lot of work surrounding the core offering that will be done.

Current Status…3 years and counting.
It’s been an amazing 3 years and I’ve accomplished nearly every goal I set for myself (while having a baby — that’s a whole other article). I’ve run Design Sprints for clients of all shapes and sizes including Ameriprise Financial, US Bank, Best Buy. I’ve had the opportunity to teach people how to run Design Sprints during training boot camps, run with John Zeratsky, co-author of the Sprint Book, and have led training initiatives for product teams in startup and corporate settings. I co-authored a Remote Sprint Guide with (John and Jake, the authors of Sprint) at the start of the COVID19 pandemic to help teams move to remote collaboration more easily.

What I’ve learned

There are things about running a solo show that suit me well. Other aspects of the job continue to challenge me — but are a part of the job and must be done. Consider these lessons and, at the same time, consider your own situation.

What are your values, interests, and experiences? One of my “pros” might actually be a “not-so-pro” in your book.

The pros:

I get to say yes and no to the things I want to — my values aren’t compromised unless I choose to compromise them.

I own my commitments and my calendar. I choose how much work to take on and am careful not to schedule myself beyond my available capacity. I plan for time off and days off as I see fit. Every day, I get to decide how to spend my time. If I’m careful, I’m able to include a walk or yoga midday. One thing to consider on this point is whether or not you are adept at planning your schedule and setting boundaries. I hear from many other solopreneurs that they have a hard time “turning off” because they are unbound by a typical work calendar and as a result, suffer from stress and burnout. I don’t wish that for you — or for anyone.

Fun. This is not something to be underestimated. I do work that I enjoy and am good at it. I also have a “no assholes” rule meaning that if someone’s a jerk, I won’t work with them. This means that I am having fun most of the time while working. I also LIKE working. It’s something that I have always taken great pleasure in. I like to solve problems, I like to deliver solutions, I like to help people work in new ways. I find work rewarding. This means that I am motivated and energized to keep going and do the work without someone telling me I have to.

The not-pros:

Loneliness. I work with clients I enjoy but I miss the feeling of crossing the finish line with teammates. I also miss office banter and comradery. There’s something about collaborating with people consistently over time — it’s a relationship unlike any other and I miss that some days.

Business development. I am fortunate to have a strong network of people I’ve worked with over the years and out of the gate, work came easily. However, as I have continued to stay in business, I’ve had to reach further out beyond my core network to talk about the services I offer. The “colder” the lead, the colder my hands get with nerves. It’s funny how even though I am confident in what I do and who I am, having conversations with strangers about how awesome it will be to work with me still makes me sweat. Is there anyone out there who does not get nervous doing this?? If yes, please put all of your tips in the comments below. I need your wisdom.

Marketing myself. This is something that has gone from being painfully hard to mildly annoying. Something unique about being an independent consultant is that in many ways, you are your brand. I know that some consultants create a separate brand to market but from my perspective, if it’s just you, that’s a bit weird. I had to make marketing a focus for the first year I was in business to get to a place where I felt decent about it. I publish regularly on LinkedIn, Twitter, Medium, and reach out directly to clients and prospective clients via email. I have to plan and schedule this work because I am resistant to doing it, but it’s a part of the job.


So what? Now what? Sitting around and thinking about going out on your own is fun. It’s even more fun to give it a try. You might find out that it’s not for you or you might love it. Either way, you won’t REALLY know until you give it ago. Here’s what I recommend before you start:

Fall in love.
Make sure you are focused on something you love doing and are good at. If you aren’t going after something you love, choose something else. You’ll need sustaining energy and leaning into doing something that energizes you is key. There will be plenty of additional work that will need to be done outside of your core focus (planning, marketing, invoicing, taxes) that will require your attention and may drain your battery. Your core offering should not.

Be uniquely you.
Rather than trying to be everything to everyone, be something meaningful to a few people. It’s tempting to want to show off all of your amazing skills. If you’ve got multiple skillsets that you can offer, kudos to you but you risk being confusing. If you aren’t sure what you want to focus on, do some competitive research. Who else is offering what you might want to offer? How are they positioning themselves? How can you learn from what they are doing? Is one of your skillsets a diamond in the rough? Do you know people who might want to buy what you’re considering offering? Talk to them. See if they want to buy it. See if they’d actually hire you. If no, find out why and use what you learned to improve.

Make sense of your dollars.
Determine how much money you need to cover your expenses for a period of 6 mos-1 year. Decide your time-horizon first (I recommend at least 6 months), then save and set aside that money. Consider it an investment in your new business. Don’t do it until you’ve reached the end of your time-horizon. It will be really hard at times and you will want to give up and just go get a job. Don’t do that prematurely. It might not work out, solopreneurship might not be for you but if you decide it’s not for you, I want you do decide based on real evidence not because you got scared and gave up on a whim. If you save up in advance and give it enough time, you’ll give yourself a chance to really learn. Best case, you’ll discover that you don’t need to spend your savings because you’re successful out of the gate and can keep that money as a nest-egg to help you weather future storms (pandemics.)

Time management.
Are you good at it? If no, get good at it.

Lean on your people.
Think about your network. Your network is your best asset. If you’ve neglected cultivating meaningful connections, getting started is going to be harder. When you start, you are going to draw on your social capital — you are going to be asking people to help you with time, advice, possibly money — this is something that should be as carefully considered as you’d consider your financial investment. Think about what your offering and what you’re asking of people before you start.


No matter where you’re at in your journey, I encourage you to continue. Dig in and really get to know yourself along the way. Take the time to reflect as you move forward and notice what’s working for you and what’s not. Ask for help. When you decide it’s time to take the leap, do it wholeheartedly. Jump in with both feet.

If you’ve got questions, suggestions, or want to know more about a particular topic please comment below. I’ll reply and may add to this post to answer questions and add value.

— Jackie

If you want to learn more about my work and endeavors → I’m Here.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Jackie Colburn

Jackie Colburn

Weekly resources for facilitators and leaders. Learn tips and methods to run better workshops, accelerate teams and uncover new ideas.