We’re trained to be employees our entire lives, fit into a box that someone else has defined, and be a widget in the larger system.  

When we’re raised in a structure where we don’t define work for ourselves, having complete ownership over what we do and how we do it can be daunting.

No one teaches us to be entrepreneurs, let alone solopreneur businesses of one. Instead of following an onboarding plan or a professional development schedule set out by someone else, you have to learn by doing, trying, and failing.

Solopreneurs must learn to be a boss in a world where most workers never work for themselves. We have to manage not only our “work,” we have to build the infrastructure, run the logistics, solve the problems, and drive ourselves toward constant improvement.

This level of agency requires a fundamental mindset shift to take full ownership of our work AND break free of the social conditioning that teaches us to rely blindly on authority. 

For solopreneurs in particular, this mindset shift can be particularly hard because we’re single-person businesses. We don’t fit into the conventional definition of a business, but we’re also not employees; we fall into a category all our own. 

And here’s the hard truth, solopreneurs – you can’t fully reap the rewards of independent work if you can’t break the employee mindset.

As long as we’re still trying to fit into boxes defined by others, letting others determine what we’re worth, and not taking charge of our own growth and development, we still operate as employees.

Does this mean we never ask for help? Far from it. As opposed to other traditional hierarchical systems, solopreneurs are inherently decentralized, rhizomatic, and microbial, building our own networks, partnerships, and support systems.

There are so many others out there who have learned by doing and trying and failing. When we take greater agency over our work, we can better support others in doing the same.

As part of that incredible network, I love to share some of the collective wisdom I’ve learned from my nearly decade of solopreneur experience and the hundreds of freelancers I talk to worldwide so that you can have a reference point to guide your journey.

This is the first in a three-part series about Boss Mindset – how to own our work, worth, and wisdom.

Let’s begin with work. 

Doer vs. Strategizer

When we work within a hierarchical system, jobs are often categorized (explicitly or not) by those who do and those who strategize. To a certain extent, we all naturally tend toward “big-picture thinking” or details and execution. Still, the truth is that these tendencies are on a spectrum, and the most successful people embrace a combination of both.

When we separate does and strategizers, we are limiting the ability of everyone to understand and embrace the broader vision of what it takes to accomplish something. We also often reinforce hierarchies between “those who do” and “those who think,” usually placing a higher value on “those who think.” 

Many solopreneurs fail because they’ve been trained to be either big-picture thinkers who can’t execute or doers who can’t strategize and dream big. When you’re a business of one, you have to be able to do both. There’s no CEO above you driving the vision of your business, and there are no “underlings” doing the grunt work.

Does this mean that you should do everything in your business? Absolutely not. The most successful solopreneurs know when to delegate and outsource. Still, they are intimately connected to the entire structure of how their work gets done and aware of their natural tendencies toward strategizing or doing so that they can strategically compensate with the support of others. 

Fragment vs. Whole

When we work for other people, we typically are only required to know about and own our “piece” of the work. We do our thing, put in our time, and then all those fragments contribute to a finished product.

Our effort is diluted when it is fragmented from the whole.

• You’re knocking it out of the park, but the person in the C-suite takes all the credit.
• You’re leaving early because you’re super focused and efficient, but the slacker in the cube next to you gets the raise because they stay late, mainly because they do nothing during the day.
• You’re phoning it in because you’ve already put in the bare minimum, and since no one recognizes your effort, what’s the point of going above and beyond?

This separation means that we don’t always feel ownership over, and therefore aren’t motivated by, the finished product or end goal. We also don’t usually understand the bigger picture or everything that goes into it, so it is hard to understand the broader causes and implications when something isn't working.

When you work for yourself, your work is entirely dependent on you. Start to finish, soup to nuts; if you don’t deliver, there is no one else to blame it on.

Likewise, if you’re unhappy, not making enough, or working too much, you must understand why and change it. You decide how many hours you work in a day, week, or month. Sometimes, we chase a full workload because it validates us, not because that amount of money will actually change anything in our lives. When you work for yourself, you get to choose rest and not feel guilty about it.

This sole responsibility means you must proactively gather and analyze data about your business to know what’s working and what isn’t. This includes both internal and external metrics – is your pricing on par in your market? Are your clients happy? Are you happy? And then you have to use that data to make a change.

In vs. On

Employees only work in a business. You put in the time to work on your “fragment” but aren’t always bought into the overarching success of the company or how your fragment fits into that success. And why should you? In most cases, the broader success of a company doesn’t equal greater benefits or rewards for its employees; it usually equates to CEO bonuses and stakeholder dividends.

As solopreneurs, we work on our businesses, not just for or in our businesses. Business owners build businesses, not just serve clients.

This distinction can be particularly tricky for solopreneurs because we feel like we have to be everything to our business, but that’s why we must be carving out dedicated time to work on our businesses, whether that’s networking, refining our products and services, marketing, financial planning, etc. 

All of these choices fit together. Simultaneous “doing” and “strategizing” are required to engage with your business as a whole. Recognizing your business as a whole manifests in working on it regularly, not just in it.

Everything changes when you see and engage with your business as a business. When you begin to own your work, you also show up differently with your clients and partners, which translates to better projects, more money, and the most fulfilling relationship with your work.

Stay tuned for the second installment in this series – how to own your worth.