What it’s really like to be your own boss

Have you ever dreamed of being your own boss? Of the freedom to choose what to work on, and when, and how? It’s a heady thought. And if you’ve ever worked for a real headache of a manager—someone who gave you too much work, hassle, and stress with too little freedom, autonomy, and credit—the idea of being your own boss is even more appealing.

Photo of Alex Vasquez

When Alex Vasquez decided to quit his job and start his business, DigiSavvy, one of his many motivations was the fact that his boss’s personality and work style didn’t mesh with his own.

I finally hit a breaking point where I knew that I just couldn’t deal with the work environment anymore. I was miserable at work. I drove 45 minutes each way to deal with bullshit. And it’s stupid. It angers me when I think about how much time I spent, in a car, going to do something I didn’t like.

He quickly found that being his own boss was hardly easier (at least, not at first). Are you familiar with the reverse golden rule? It goes like so: “Treat yourself as you would treat others,” and it’s inspired by the fact that many people are much harsher to themselves than they’d be to a friend, a co-worker, or even a stranger.

It can be especially challenging to be kind to yourself when you’re in the early stages of running a business. There’s so much to do and so much pressure. You’re constantly stretching yourself. Unless you’re unusually lucky, some things will go wrong and you’ll probably make mistakes. All of this was true for Alex, and as a result, he was his own critical, demanding boss.

I wasn’t a really good manager to myself. I didn’t give myself time off. When I made mistakes or I lost deals, I was really really hard on myself.

*There are a couple of people who work for me now, and I would never want them to feel the way I made myself feel. I would never want to make them feel anxious about the work they do and I wouldn’t want them to question whether or not they’re doing a good job. I should have been much, much kinder to myself. *

After less than a year, he was burned out and ended up deciding to take a break from entrepreneurship. When he came back and decided to give self-employment another shot, he realized a big part of the work involved was going to be learning self-compassion and stress management.

Now, after 9+ years of entrepreneurship, he’s learned a lot about what it takes to be a good boss to himself and his team.

Make your business a great place to work

What makes a company a great place to work? The answer depends on who you ask, of course, but most folks will answer with one or all of the following:

  1. A balance of freedom and direction
  2. A living wage
  3. Benefits like health care and retirement accounts
  4. A collaborative team
  5. A supportive manager
  6. Opportunities to learn and grow
  7. Enough time off of work

Self-employment typically comes with many advantages (autonomy, flexibility, the ability to choose who you work with, and the growth that comes with constantly stretching to learn and do new things). In fact, recent surveys show that self-employed people tend to be happier and more fulfilled than their employee counterparts.

That said, there are many things that employees take for granted that are surprisingly challenging for entrepreneurs. For example, Alex says that taking his first vacation was an intimidating, anxiety-provoking task.

It wasn’t until my third year as a business owner that I took any sort of real vacation. There’s just this anxiety, you know, about what will happen to the business if you’re gone. You have to put a little bit of faith in your ability to plan and get things done. You have to have faith in yourself to set up things the right way, and then confront the fear that everything’s going to burn down while you’re away.

*There’s also the cost. It’s not just the hotel and travel and everything. There’s the cost of making sure that everything is supported while you’re gone. I had to make sure there was someone who was empowered to make decisions on my behalf while I was gone. And, you know, that’s not an easy person to find. *

To make it happen, he hired a freelance project manager that he worked with in the past, entrusted her with decision-making power, and told her she could call him if things started burning. Then he left and really unplugged for the first time in years.

That vacation, he said was great, and much-needed, and an important step towards creating a healthy, sustainable balance in his life. It wasn’t easy, though, and the work wasn’t over—even now, after many years as a business owner, he says that it’s still hard to take time off.

*One trait that I need to work on is anxiety and fear of the unknown. There’s just something inside of me that’s always planning for the worst-case scenario and I don’t think that’s necessarily healthy. I don’t think that’s necessarily good. But I’m getting there, you know. *

Another challenge, he’s found, is creating his own plan for personal development.

Personal development is kind of a weird challenge because no one else is driving that. I think this is a source of anxiety for a lot of solopreneurs, or anyone who’s captaining their own ship, so to speak. No one’s telling you to get better at this. No one is telling you where to improve. There’s a sense of unrest—and maybe anxiety—that you’re not pushing yourself to grow.

If you’re a brand-new entrepreneur or you’re thinking about making the leap, it’s probably not necessary (or even helpful) to start worrying because you don’t have a detailed plan for retirement, personal development, or regular vacations all at once. However, it is helpful to keep these general needs in mind—that way, you can work towards them as you build your business.

Is it worth all the work?

Being the boss is a lot of work. But it’s clearly worth it for the people who lead the 30.2 million businesses in the US (and the much greater number of entrepreneurs worldwide).

For Alex, one of the payoffs has been seeing people—himself and others—face challenges and doing things that previously seemed impossible.

After the years running my own shop, I feel more confident about getting things done. I believe in myself a lot more than I used to. You gain a certain measure of confidence as you keep going and continue to grow. That comes from just being persistent. So, I think you end up believing that there’s not that much you can’t do.

It’s also really neat to see the people who work for you grow. I’ve had a couple of people who work for me that came a long way. They did their thing and they did really good work for me. They were really unsure of themselves and the work they were doing. To see them build their confidence, and be able to have confidence in doing good work is awesome.

Then, of course, there’s the freedom and the ability to spend your time and energy on the things that are important to you—not someone else.

So yes, being the boss is hard, and messy, and you won’t be perfect—but that’s pretty much the essence of entrepreneurship. Entrepreneurs are people who care enough about the benefits and opportunities to get through all the challenges.


Hi there! This post exists to offer you (hopefully) useful information but it cannot take the place of personalized professional advice. Please consult a qualified expert if you have questions about your business. Also, Azlo doesn’t endorse any third-party sites that are linked here.


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