How to Decide if Entrepreneurship is Right for You

By Sean Ogle •  Updated: 02/25/14 •  7 min read

is Entrepreneurship is Right for YouFor the last five years, I’ve spent a lot of time with entrepreneurs – perhaps, even too much.

The traditional advice is to spend time around the people that you’re striving to be like. Well, for my whole life I’ve wanted to be an entrepreneur – so it was the natural fit.

Trips, meals, parties – they’d always be about strategies, tactics, big wins, lessons learned, and generally how we could take our businesses to the next level.

When you’re surrounded by that for so long, there’s a part of you that almost begins to think that owning a business is the only way of doing things – even though it most certainly is not.

On a different level, I’ve come across quite a few people lately that have spent weeks if not months reading blogs like mine, researching make-money-online options, thinking about starting a business – but not pulling the trigger.

Is it because of the uncertainty? Is it just because they’re afraid of what might happen and don’t want to take the risk? Or is it something much more fundamental than that?

Maybe becoming an entrepreneur simply isn’t the right fit.

I was catching up with a good friend last week, and during the call I was listening to her talk about the rollercoaster of emotions she’s been going through over the past few months.

She has an unbelievable job – like the kind of job we’d all kill to have. However last time we talked, she was preparing to leave it to do something else.

Listening to the Herd Mentality

In the time since I last spoke with my friend, she’d started questioning everything about her plans. She’d started hanging around a lot of entrepreneurs and “unconventional” folk who were all telling her the same thing: “Start a business!” “Go out on your own!” “What are you waiting for?!”

When that’s the only thing in your ear, it can be difficult not to think that way.

The reality is a lot of those people have their own motivations, so you can’t base your entire life on what a very small subset of people think.

What do I mean by that?

I know a lot of people who have started relatively new businesses, and are still very unsure of themselves. They lack confidence, and are still questioning whether or not taking that path was the right decision.

These people can often be the most vocal proponents of entrepreneurship. “I have so much more freedom! It’s the best thing I ever did! Come join us!”

If you’ve found these people, maybe you’re friends with them back home, or follow their blog or social media feeds – it can be easy to be swayed by their enthusiasm.

While many advocates of entrepreneurship absolutely have successful businesses, great products, and are balanced in the way they spread their message – many are not. And if you get too caught up in the hype, you could end up making major life decisions for the wrong reasons.

Because of this, when I’m talking to people about starting a business, I like to walk them through a few questions to help them make decisions for themselves about whether or not starting a business is right for them.

How to Discover if Entrepreneurship is the Right Fit for You

Question #1: Are You Happy?

Pretty simple, right? It’s a much tricker question for most people than you might think.

The fact is, if you’re absolutely truly happy in your life – why change? That’s what this whole life thing is about anyways. Your happiness should always come first and foremost. If you’re not happy, then you won’t be able to give your best in the way of helping others – in whatever form that comes in – and that’s really what starting a business is all about, helping others in whatever capacity they need it.

So if you’re truly happy with what you’re doing now, there’s a good chance you should just keep doing that, even if it’s a 9 to 5 job that proclaimed experts think you should leave.

Question 2: Is the Pain of Staying Worse than the Pain of Leaving?

This is a similar question to number one, and it pertains to those wanting to quit their job and then start a business. “How do I know when I should quit?”

You should quit when the pain of staying is worse than the pain of leaving. Only you will know when that time is.

Question 3: What Do Your Savings Look Like?

Simply put, the more money you have saved up, the less stressful starting a business is. If you have $400 to your name, you essentially need to make money right away – and there are businesses you can start where that becomes possible, but for most people trying to do that isn’t feasible. You should have a buffer with which to invest, and not have to choose between your business or food on the table.

Question 4: What Type of Business Do You Think You Want to Start?

Are you simply trying to make $1,000 bucks a month so you can travel the world indefinitely? Do you want to get funding and go the typical startup route? Do you want to build an independent business that gives you the freedom to do what you want, when you want?

What type of business is appealing, and why? Have you even thought about it? If not, if you’ve just said “I want to start a business”, think about why that is, and if you really do – or just think you do.

Question 5: Why Do You Think You Want to Become an Entrepreneur

Quite often the response to this, is “because blogs like yours told me I should.” Fair enough, but not the best answer.

I advocate starting a business online for those who are unhappy with what they’re doing and looking for another way. I’ve seen it work for a lot of people, not the least of which is myself, but if you’re starting something just because I said it was a good idea or because you think that’s the fastest way to a billion dollars – you might want to get your priorities straight, and then about whether this is really the right choice.

Consider These Questions and Then Decide…

My guess is half the people reading this who might have been on the fence, will ask themselves these questions and if they’re honest, they’ll realize they don’t want to be an entrepreneur.

For many they simply need a different job, a different relationship, a new hobby, a change of scenery, more exercise or a good adventure. Entrepreneurship can help with all of those things, but only if it’s the right person.

After going around in circles for months, questioning the sanity of leaving her job, my friend finally decided that she really did want to become an entrepreneur and start something on her own. But it took a few months of questioning her motivations, soul searching, and eventually blocking out all of the people who said “you should do this” – to figure out for herself, what she truly wanted.

Listen to yourself, you’ll know if it’s the right fit or not.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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