The not-so-solo Solopreneur
All the reasons why you shouldn't chase solopreneurship
There’s no irony in the timing of this newsletter. If you’re reading this the week it’s originally published, this is also the same week I filed for DemandLoops’ LLC in 2023–I’m officially 1 year into this journey. And what a year it’s been!
This week has ushered in a wave of reflection and I can’t help but feel overwhelmed with gratitude and proud of everything the last year has brought for myself, my family, and the clients I’ve been fortunate to support.
But truthfully, I feel as though I’ve been holding my breath for the last year.
Waiting for the luck to run out, the “shoe to drop” as they say.
Nervous at the prospect of a confrontational client call.
Expecting the pipeline to dry up entirely.
Terrified of failing—publicly.
Deep exhale.
Honestly, it feels good to type out those words. Despite all my fears, it’s safe to say, I love being a solopreneur. And none of those fears are today’s reality.
All to say, I totally get it. This isn’t for everyone. And I certainly don’t want to encourage the wrong people to give up a steady W-2 job to try solopreneurship.
So, here’s a word of warning based on year 1. If these 10 things are true, solopreneurship might not be the path for you.
You don’t have a financial cushion
(think: income, health benefits, retirement, etc.)You need to be told what to do
You don’t have creative ideas
Your capabilities aren’t marketable
You don’t have the patience
You don’t like taking risks
You would rather chase wealth than freedom
You care too much about what others think about you
You get lonely without structure
1. Financial Cushion
Best case, you start your solopreneur venture on the side while still holding down your full time gig. This would allow you to start experimenting with your offer, then pricing and packaging.
Of course, we aren’t all afforded this scenario, so somewhere between 6-9 months of cushion in case it takes a bit to find your footing would help to ensure you can spend as much time in the business as you do on the business in the first year.
And, for those of us in the States, health insurance is a real thing you’ll need to figure out. Either through the open market, or a spouse-sponsored plan.
2. Self-starter
“The best solopreneurs were often horrible employees.”
In this lane, there won’t be anyone managing your time, or prioritizing your projects. You will struggle as a solopreneur if you don’t know how to plan your work, leverage your calendar, and stay focused to get things done.
3. Creativity
Building and operating a successful business will take some level of creativity.
You will come up with the original business model and design your plan around it.
You will have to identify the need to zag when the market zigs.
You will now be your marketing team, sales team, and back office.
You will have to read the market to understand the gap and craft an offering you’re able to deliver.
4. Capabilities
Speaking of crafting an offer you’re able to deliver…
“Solopreneurship is about treating your brain as a product and building a one-person company with a predictable, sustainable, and competitively defensible growth model.”
- Elena Verna
Solopreneurs often translate their talents, knowledge, skills, and experience into services they can market to potential customers. Or, they use their skills to create something that can be sold (i.e., goods).
The good news is if you have capabilities that an employer already pays you for, you probably can package that up to sell directly to customers. But, if you’re not able to market them to direct buyers, that could be a problem.
5. Patience
Look, this just doesn’t happen overnight. It could take you months, or even years, to really identify an offering worth building and scaling. Creating unique and defensible positioning might be something you have to experiment with in order to nail. And then generating lead flow for consistent pipeline is another potential hurdle.
Just like an exec in a startup, you’ll find you might need reminders often that there are little-to-no silver bullets in this life. Patience will be key.
6. Risks
There’s no two ways about it, starting a new business is risky territory. If you ask me, W-2’s (especially after seeing what went down post 2021 in the SaaS space) are risky too, but I get it. Something about standing up an S-Corp and being truly on your own just feels different.
Framing it like this might help. You assume risk every day in your life.
When you jump in your car in the morning and head out on the highway with other drivers, you’re assuming risk. When you sign a non-compete with an employer, you’re assuming risk. When you stand up your S-Corp and start sourcing clients, you’re assuming risk. What level of risk are you comfortable taking?
7. Wealth vs. Freedom
Can you become wealthy as a solopreneur? Sure. I know plenty who have. I guess wealthy is also relative. There just aren’t any guarantees.
If you’re able to build a business working with clients you love for 25 hours week bringing home enough revenue to live a stable lifestyle, is that “success” for you? Or would you be miserable?
If you’re seeking solopreneurship because you value wealth over freedom of your schedule, the clients you work with, the projects you build, this just might not be the path for you.
8. Confidence
If you care too much about what others think about you, you may struggle with solopreneurship. Running a business like this is not what most people do. Your friends with 9-5 jobs might think you are taking a big risk and making a mistake. They may even make fun of what you do. Or just not understand it at all.
Do you have the confidence to stick with it despite what others might say?
Are you prepared to be more visible on social media?
Are you ready to market your business, products, and services online?
You may find it challenging to be a solopreneur if you worry too much about the opinions of others. Having a point of view and getting noticed often requires being strong about your beliefs and saying polarizing things. Not everyone is cut out for that. And imposter syndrome is real.
9. Loneliness
Lastly, loneliness. Some people need the structure of a job and coworkers around them. They find they get too lonely when they work on their own.
As a solopreneur, you often work by yourself. If you want supportive peers, helpful mentors, and like-minded friends, you will need to find them for yourself. You won’t have a boss putting you into a cubicle surrounded by coworkers.
If you’re not good at networking, you may struggle with solopreneurship. But then there’s my perspective. I’ve found I’m the not-so-solo solopreneur. I thrive on higher degrees of accountability, and luckily enough, there are so many that have gone solo recently that we’ve all found a way to lean in, support one another, share critical feedback. My spin on this is that I’ve now chosen the best team of coworkers I’ve ever had.
So, I’m not saying not to go solo, but I’m also not saying to go solo, if you catch my drift. If most of these things are your personal truth, a solo route might not be ideal for you, and the best thing is, that’s totally fine. In this echo-chamber social media culture we find ourselves in today I feel most people doing something because they feel the pressure from the feed to conform. But there’s also so much to be said for forging your own path and zagging the status quo. Just gotta figure out what that means for you.
If you’re looking for tactical advice to going solo, check out Nick Lafferty’s Substack. Or shoot me a DM, I’d love to help.
Cheers,
Kaylee