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Do You Really Want to Be Your Own Boss? Answer These 6 Questions First.

Do You Really Want to Be Your Own Boss? Answer These 6 Questions First.
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Starting a business is like building a boat from scratch and setting sail. Unless you build boats for a living, expect things to go wrong very quickly.

Related: The One Basic Skill Every Startup CEO Needs

To continue the metaphor: The problem with many would-be entrepreneurs is that they only have experience on the open water. They know how to sail, navigate and survive at sea. They’re sailors, but they don't have the skills to build their ship. They just have sailing skills.

I didn’t make the decision on a whim to start my company after I was fired from my last full-time job. I was already in the right industry, had learned from some of the best minds in the business and was freelancing on the side. In other words, I had a good sense of how to build a boat and captain my own ship.

If you too want to start your own business but have experience working only under a manager, you need to do some serious soul-searching and self-assessment. Ask yourself these six questions before you start:

1. 'Could I survive, financially and psychologically, poorer than I am now?'

According to the U.S. Census Bureau, more than 543,000 small businesses are started in the United States every single month. Yet, somehow, more businesses shut down than start up each month. Those aren’t exactly great odds for a newly minted entrepreneur.

Unless you’re some transcendent genius, chances are you’re going to fail at your first business. And that’s totally normal -- more than 543,000 other business owners will be in the same boat. Even if you do “succeed,” you may end up making less than you do with your current full-time job.

Countless success stories, including J.K. Rowling’s, began with a life of modest means. Can you live at a level even lower than you do now?

2. 'Could I work on something alone, and without encouragement?'

It’s certainly fun and games thinking about a great business idea -- but executing it is another story entirely. As Freelancers Union founder Sara Horowitz discovered when she created a health plan for freelancers, remote work can be very lonely. “You work with coal miners and you learn everything there is about black lung . . . You work with freelancers, and you learn about depression," Horowitz has said.

Freelancers have been found to have poorer mental health and higher stress than their full-time friends. This isn’t that surprising when you consider all the risks associated with starting your own business. Sure, you get to control your schedule and be your own boss. But you also have to work longer hours, usually in isolation, and potentially make less than your full-time friends.

One Dutch study found that freelance workers have a hard time separating work from home, and are more likely to become workaholics. Can you see yourself working that much?

Related: 8 Tech Skills Entrepreneurs Must Have to Succeed

3. 'Do I want to learn marketing, sales, accounting, etc.?'

When I started Tailored Ink, I quickly realized there were several skills I didn’t have that I would need to learn very quickly. If you’ve only done design, for example, that’s not nearly enough to run your own design agency. Instead, most business owners will agree that you need to learn the following five core business skills to be successful:

  • Sales: so you don’t starve

  • Marketing: so you can sell more

  • Management: so you won’t be alone

  • Planning: so you can scale and stay competitive

  • Adaptability: in case your plan doesn’t pan out

Of these five core skills, sales is by far the most important.

4. 'When it comes down to it, am I an overachiever?'

When I was younger, I spent a lot of time playing video games. In fact, I’m convinced mastering video games taught me soft skills essential to business success.

Most importantly, playing thousands of hours of games helped me realize that I am fundamentally an overachiever. When I have my sights set on an achievable goal, I’ll doggedly pursue it before moving on to the next goal. It’s hard for me to live in the present and just enjoy what I’ve accomplished -- I’m always thinking of where I want to be next.

I’m not saying that this is the best way to be, just that it’s part of my personality. And it’s helped me accomplish a lot within a short amount of time.

5. 'Can I comfortably delegate tasks to others?'

This is something that doesn't come very naturally to me. When I became an entrepreneur, I had had experience tutoring, teaching and managing, but when it came time to delegate tasks that affected my earnings, I was much less enthusiastic.

As an introvert, I find it very easy to be self-reliant. And, unlike extroverts, I draw energy from being alone; I’ve spent most of my life being proudly independent.

But that only works if you’re a small-scale solo freelancer -- not if you’re running a serious, growing business. At some point, you’re going to have to delegate. And that means finding, training and trusting in people whom you won’t be able to keep tabs on all the time.

5. 'Would I be a good mentor?'

You can’t delegate effectively without knowing how to manage effectively. And, despite what many business coaches would have you believe, management isn’t just knowledge-based. In the words of Admiral Grace Murray Hopper, “You manage things; you lead people.”

Even if you have an MBA and understand how to manage on a logistical level, you could be driving away top talent. It’s not enough to know how to manage, you need to want to manage, too. And that means being a mentor.

Does the very thought of managing others make you cringe, or does it excite you? Do you take the time to explain things when a colleague asks a simple question, or do you get annoyed? Do you care about your coworkers and what’s happening in their personal lives?

6. 'Do I still want to build that boat?'

When you really think about it, the first person who decided to tie together strips of wood and head out into deep water must have been a little crazy. The innovators of today, like Elon Musk, are just as crazy, in their own way. They have a healthy appetite for both risk and failure.

You don’t need to be as bold to start your own business -- there are plenty of boat-building manuals and playbooks out there that you can follow. Maybe you’re building the kind of boat that other people have built before you. That’s absolutely fine! It’s what I did, too.

Related: The One Skill That's More Important Than Selling for a Startup Founder

But you do need to be honest with yourself about the skills you have and the skills you have yet to learn. It’s best to figure all that out before you hit stormy weather.