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Solopreneur Surprises: You Don’t Have to Struggle Alone

The Trials of Going Solo

Most solopreneurs started out working for somebody else. They worked hard. They were good at their job. And then one day they started to wonder.

They saw a different life in their head.

They made a decision.

They started a business.


If this is YOUR story - awesome!


If you’re not prepared for what being a solopreneur is like, that exciting vision can turn a little…suffocating.

Being a solopreneur can be lonely. You can feel swamped by “have-tos” and overwhelmed by decisions. You can lose track of what’s important. If you’re not careful, you can turn into a sad, isolated, stress-bot.

And it can feel like it has to be the way. It doesn’t. You just need to prepare for those little solopreneur surprises - and deal with them like a pro.

In this blog, I want to discuss a handful of the challenges you might not see coming when you go into business for yourself. And what you can do to navigate them successfully.

Employee Mindset + Solopreneur Passion = Ick

Before we go further I want to talk a little bit about your mindset.

Most of us come from some kind of employee or freelance experience. And when you move into the solopreneurship setting, there’s a lot of mindset carryover from that life.

The passion of a solopreneur mixed with the memory of being a jobber can really hit your identity hard.

Being a solopreneur requires better-than-average boundaries. You need to create structure, delegate, essentialize, and return to the long-term mission constantly.

Don’t worry. You don’t need to know how to do everything immediately.

But I advise you to check your employee/freelancer mindset at the door. Once you do that, you’re in a better position to create a more sustainable, lucrative, and fulfilling solo business.

Solopreneurs Never Feel Done

Anyone who knows me knows that I loooooove checklists. But when you’re in business for yourself, that checklist can turn into a monster. You add things way faster than you check them off.

The concept of DONE just keeps getting further and further away.

When you’re the whole operation, there’s no clear delineation between work time and weekends. Everything is your problem. The universe is your office.

You're running in circles. Never clocking out. This is a recipe for burnout. And burnout can mean real suffering - emotionally and physically.

Studies show that burnout is a big predictor of heart problems, diabetes, breathing issues, gut problems, injury, insomnia, depression, and hospitalization.


This is not what you became a solopreneur for.

The Antidote

Here’s the thing, the I-gotta-do-one-more-thing problem? I get it. It’s real.

I mean, we ARE never done. There IS always one more thing to do. So first - I want you to be ready for it.

Then I want you to take a breath - because there are ways to deal with this. Some of it’s about outsourcing - which we’ll talk about it in a minute.

But you also want to:

  • Create a schedule with a lot of open buffer times. Take Breaks.

  • Batch dependable “have-tos” together. Don’t scatter them throughout the week.

  • Create your checklist before the day begins - so you’re not in reaction mode all day.

  • When new things come up, throw those items on an overflow checklist for the next day. If you keep adding to today’s list, you could get demoralized fast.

  • Set realistic expectations - it’s not about finishing. It’s about getting important things done.

The Loneliness of Being A Solopreneur

Loneliness is a real problem for even the most passionate solopreneur. It can really sneak up on you. You might not even recognize it as loneliness at first.

But it’s super common. “Loneliness is one of the biggest shocks for new solopreneurs,” warns Entrepreneur, “You spend days and nights working on your business, trying to create processes, make sales, make a positive impact, and share value with your clientele. It's usually only when you stop to take a breath that the realization hits that you are all alone…”

It can hit you particularly hard if you’re the first entrepreneur in your circle.

Even if you have strong personal relationships, your loved ones are going to have a hard time understanding what you’re going through. This can rev up feelings of isolation.

Create A Cohort

Look into joining a mastermind, a coaching group, or even connecting with some kind of meetup community.

Seriously. Do this.

Aside from accelerating your learning, you’ll see your issues echoed, your struggles understood, and your experiences appreciated in this entrepreneurial peer group.

It may seem like a luxury. It’s not.

Head off isolation before it takes root. Don’t let it become a habit. Create or join a solopreneur cohort. Then shield that time commitment. It could be what keeps you sane and balanced.

Perspective and Priorities

This is a good time to talk about perspective and priorities - both are really hard when you’re the only one on the team.

When you’re a solopreneur, you don’t have the pushback of other minds. You don’t have the assessments of outside partners. It’s really hard to tell when you’re straying from the mission or getting bogged down with inessentials.

Your inner freelancer can start jumping thoughtlessly from chore to chore without direction or purpose. It’s too easy for a solopreneur to lose their way.

Prioritize by Outsourcing

So - make peace with outsourcing a lot of your work.

Some newbies resist the expense of outsourcing. But good, experienced help will be the best investment you can make for your business.

“[Y]ou have to get crystal clear on your priorities and eliminate or outsource everything that does not create a massive impact on your business,” Melissa Eisler of Wide Lens Leadership told “ Take a step back and look at your goals, tasks and calendar and remove the nonessentials. It is a mindset of doing less, but doing it better.”

Remember that when you’re a solopreneur - you’re the unrepeatable element in your business. Delegating all the non-core items opens up your schedule for the things that only you can do.

Borrow Perspective

Next, let’s face the perspective problem.

You need pushback. We all do. We need to test ideas. We need to be challenged. We need to be exposed to scary news and reminded of what’s important. We also need to be inspired when we want to give up.

Soloprenuers aren’t great at doing both sides of this conversation.

Yes, I’m going to say it - a business coach should be incorporated into your solopreneur strategy. Or at least a good mastermind group.

We all need to borrow seasoned perspectives. "I needed to have an outside opinion to ensure my thinking and perspective weren't too skewed," Serenity Gibbons, of the NAACP, told Someone “who could push me on those points I knew I had to improve, but had been avoiding.”

Outside perspectives are what successful solopreneurs use to direct time, money, and effort in more productive directions. It can help disrupt bad patterns and move you toward your vision.

The Bottom Line

When you’re a solopreneur, it’s hard to remember you’re not a god - making all things possible. And you're not a cog - meant to make every little thing happen.

You’re more like the captain of a boat that’s carrying a priceless message.

And captains may direct the ship, but they have help.

Yes, you’re a solopreneur - but you’re not really supposed to do everything alone.

Bring in help - peers, professionals, coaches, friends. Make your crew. Then lean on them. Delegate, listen, ask questions, and even tap out for a break sometimes.

Being committed to a business is great. But carrying a business on your shoulders isn’t the point.

Your business is a tool for living a better life.

If you’re going to overcommit to something - commit to that.

You don’t have to be all alone in this! Join our Brave Biz Lab and get some perspective.

A FREE coaching call every month with a different theme.


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