Long-haul solopreneurship

Some things get easier the longer you’ve been a solopreneur. But not everything. This week, we look at navigating the very real, very persistent headwinds.

There’s a belief that everything gets easier once you’ve been working solo for a while.

Sales conversations are less stressful. You understand the nuances of your finances. You manage your time better because you know the cadence of your work.

But there are still moments when even seasoned solopreneurs get that punched-in-the-stomach feeling. We try something, and it fails, bigly. A schedule gets blown up, and deadlines go zipping past with enormous consequences. Someone we were counting on lets us down (or worse).

In times like this, I rely on the self-knowledge and emotional resilience I’ve built up over time. It’s a mental muscle that long-haul solopreneurs develop. And like maintaining your biceps or quads, it requires some regular workouts to stay strong.

Success is an inside job

Sustaining a solo business is 90% mental. Yes, you need strong cash flow and sound business systems. But that all falls apart without the flexibility, self-compassion, and grit to persevere.

Let’s unpack three ingredients that contribute to solopreneurial longevity.

Emotional resilience

Long-haul solopreneurs develop the ability to adapt to stressful situations or adversaries. They’ve learned how to bounce back stronger from setbacks.

There are many ways to build this resiliency. For me, it helps to take time for regular self-reflection and recognize that these setbacks are a natural part of the process. I also try to reframe failures as “tuition” for solopreneurship (which I wrote about in an earlier newsletter).

That’s not to say that these setbacks don’t sting. Just last week, I lost 6 hours of work on a newsletter after Substack decided to eat it. I was numb. I gently told myself to get up, walk out of my office, and come back later. That evening, I rewrote the newsletter from scratch, telling myself not to trust that process again (tuition paid) and to move on.

Reflecting on this later, I realized that this stumble might have sidelined a younger me for days.

What strategies can you put in place for maintaining resilience?

Support systems

Jim Rohn was an American entrepreneur, author, and celebrated motivational speaker who penned the well-known adage: “You are the average of the five people you spend the most time with.”

The implications of Rohn's insight for one-person businesses are profound. Since we spend so much time on our own, the individuals and groups we affiliate with influence us greatly.

Even the most self-reliant solopreneur will face moments of doubt, exhaustion, or confusion. Having trusted individuals to turn to can make all the difference. They can lend support or offer a perspective that we might overlook when we’re mired in emotion.

Although it takes time and energy, meeting new people is easier than it was before the pandemic, thanks to virtual classes, conferences, and communities. When you enroll in an online course or community, for example, you join a group of people who share your passion for the subject matter. I think of it as a magical magnet, drawing those with similar values and interests together in a virtual space.

In the last few years, I’ve made new friendships with solopreneurs around the world thanks to such online gatherings. Since we’ve developed such strong connections online, any subsequent in-person meetings become even more meaningful.

How might you meet some new solo colleagues who share your interests?

Self-care

Due to our increased independence and responsibility, solopreneurs often put our own needs last. This often leads to isolation, depression, or burnout. Being mindful helps us stay aware of our emotional needs.

A mindfulness practice can take many forms. Meditation, regular exercise, and non-work interests and activities help set boundaries when work becomes all-consuming. Some solopreneurs find clarity in daily journaling or time in nature, disconnecting from work pressures. It’s important to discover what resonates with you.

Physical health, nutrition, sleep, and social connections are all facets of self-care. For solopreneurs, scheduling self-care, just like business tasks, keeps it a top priority. For me, I know my sleep often gets short-changed, but my 3x/week pilates classes get scheduled weeks in advance.

What mindfulness and self-care options do you find most appealing?

Protecting our most important asset

These three elements — resilience, connections, and self-care — not only rejuvenate the spirit but also bolster the mental and emotional stamina required for long-haul solopreneurship. If we’re healthy and happy, the working solo journey is easier, more enjoyable, and much more sustainable.

Ultimately, it’s up to us to protect the most important asset in our business — ourselves.

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Which of the three elements resonated most with you? Do you have favorite practices or tips to share? Please add them to the comments so we can all make our solo journey more sustainable for the long haul.

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