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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16 comments on "How to Decide if Entrepreneurship is Right for You"

  1. Adrian says:

    Hi Sean, really important Q’s for people to think over and i couldn’t agree more.

    I joined Location Rebel because i knew i desired the freedom to work when and where i wanted to. The idea of having easy to implement business blueprints made it an easy buying decision and i am so glad i did.

    I know many of the members have been implementing the blueprints with great success and seeing more each week achieve location independence is really cool. HOWEVER I am not implementing any of them at the moment and it relates to one of your points above:

    “If you’re not happy, then you won’t be able to give your best in the way of helping others”.

    You see i am self employed mortgage broker who doesn’t enjoy doing mortgages! After spending time in LR i realised that running away from it outright was a bad idea because using many of the strategies you teach i can actually come at the business from a different angle so that (a) i can focus on the bits i ‘love’ doing; and (b) i can remove myself from the mortgage transaction (by joining a team that can do them for me) and thus allow myself to be location independent.

    As a result i will not be creating something from scratch but using my current expertise and new strategies learnt to serve both my clients and my needs. So i am currently building a blog called which will fly in the face in the industry norm and be all about adding value to the client for life not just when they get a mortgage.

    Once i have stabilized this new system, it will free up many hours per week that i can then use on ‘passion projects’ and living the life i desire – including lots more golf 🙂

    Thank you for being a BIG part of the change. Regards Adrian

  2. Jan Koch says:

    Very good points Sean!

    In fact, I struggled with this question myself. I wondered whether I was starting a business just because some people around me “infected” me with their enthusiasm or because it’s the right thing for me to do.

    What really helped me was to take a close look on my perfect lifestyle, the daily routine that I wanted to achieve – just based on my honest feelings and not about what society defines as success or must-have.

    That exercise assured me that starting a business is right for me. Doing so on the side kept pressure of my shoulders in the first months and now I’m self employed and feeling better than ever before.

    Keep it up Sean, I find your posts very inspiring 🙂


  3. Awesome post Sean, thanks. I couldn’t agree with you more. Entrepreneurship isn’t for everyone. Sure it’s sexy and there are many perks to being an entrepreneur, but there are also many disadvantages. I guess if you’re following your heart and your passion, successful or unsuccessful, it’s all worth it in the end. I always ask myself the question, if my passion made me millions of dollars or not, would I still pursue it? My answer is the same every time…. Definitely! Thanks again….. Cheers!

  4. Anyone interested in entrepreneurship should get: Personal Brand Planning for life, available on Amazon to determine their unique skill set and persona so that they can market their entrepreneurial idea(s) more effectively.

  5. Perfect timing Sean–after reading your blog for several years (even before I graduated college) I recently hit the breaking point with cubicle life and am starting to do freelance copyediting–hopefully I can build it into something that can support me and my desire to travel more full-time one day. It’s exciting to finally be taking action on something that’s been bouncing around my head for so long.

    Again, great post. It reassured me that I was going down this path for all the right reasons.

  6. Shaleen says:

    Well.. my idea is of blogging is to do justice to my writing skills plus supplement my income a bit. I mix the technical knowledge of my qualification (Chartered Accountant + MBA (Marketing) ) with fun. Its Going quite well. Just want to make grow to be quite sizable. So yes, my blog and my qualification is my business.

  7. Glenn David says:

    Hii Sean. This is the guide every person must read who starting here as an entrepreneur.
    You covered all the important points in story and it was well plotted.
    These days I see lots of people choosing blogging rather than any other.

  8. Scott Asai says:

    You’re right about fit. I’ve always dreamed about having my own business so 7 years ago I took the leap and never looked back. Money isn’t as stable, but flexibility is key. I’ll do anything NOT to work a 9-5, so that’s how I know being an entrepreneur is right for me.

  9. Robert says:

    good stuff, bookmarked !

  10. Chas says:

    This is a great post, Sean. Entrepreneurship isn’t for everyone. I like Scott Asai’s comment. I grew-up in a time when the word ‘Entrepreneur’ was hardly ever used and the idea was to get a good paying job with benefits and climb the corporate ladder. Anyone who struck out on their own was considered ‘crazy’ and not the more flattering description, as being a ‘Maverick’. Of course, we live in a time, now, where the ladder is broken and ‘entrepreneurship’ is glorified and the hard facts of starting something on your own are glossed-over. For every Facebook, or Tumblr story, there are thousands of stories about a coffee shop, or food cart that has to close the shutters, because they are losing money. It isn’t an easy path to follow, but, that doesn’t stop people from trying. The key is to listen to your own inner voice and what it is telling you.

  11. Ragnar says:

    It’s funny in a way. I like to think of the lifestyle design community in the same way I think about hipsters, they might reject the general population’s way of doing things, but in turn they are extremely influenced by a smaller group of people. Their peers and idols. Not trying to exempt myself from that, I’m the first to admit that I’m heavily influenced.

    The idea of being able to choose what skills to learn, when to work, where to work, is more important to me than the idea of building a business. If someone offered me a job that gave me the kind of flexibility I want, I wouldn’t hesitate to take it. But to get to that point I have to prove myself anyway, and once I’ve succeeded on my own, perhaps I’ll feel differently about taking a job, haha. Only time will tell.

  12. Question 2: Is the Pain of Staying Worse than the Pain of Leaving?
    how to know what the pain of leaving is like if you have not left yet.

    Great post though, sometime, it is just a need to have a new job, or a need to run away from the routine.

  13. Isabella says:

    I left my secure job 4 years ago to head off to Rome to make a new life (I’m Australian). However things didn’t pan out like I thought they would so I headed back to Australia.

    I didn’t want to go back to the 9-5 job so I decided to try an online business. Well I started with eBay selling second hand stuff. Didn’t like eBay one bit. Then I was told about “The Challenge” a brainchild idea by Internet Guru Ed Dale. For free he taught you tips and tricks to run a successful online business. He said that you need to pick a niche that is not highly competitive. He gave us the tools on how to find that niche. I picked Spirulina. I loved every minute of building the online business around it. Spirulina actually improved both my health and my mother’s.

    Then I went into the weight loss niche. But with the inconsistencies in that niche I soon lose heart in that one.

    Four months ago I realized what my true passion was.

    It wasn’t until I was instructed to write down the top 20 influencers in my life. Now I could not think of one weight loss influencer that enhanced my life. But you know what? I noticed that what sprung to my mind were names like Bob Proctor, Brian Tracy, Dr Joe Dispenza, Louise Hay, Wayne Dyer, Rhonda Byrne, Sandy Forster, Lynn Grabhorn, Richard Branson etc. etc. Names just kept coming into my mind, non-stop. That’s when I knew that the online business for me was in Personal Development – How to Create the Life of Your Dreams – How to develop self-confidence – How to improve your health naturally – How to increase your wealth using the principles of Law of Attraction plus goal setting.

    So in November 2013 I started my new online business. Now I have laser-like focus in my online business, the passion, the commitment and the love. As you teach you learn. I have learnt so much in the personal development field and it is helping me achieve my goals and increasing my self-confidence. What a business to be in 🙂

  14. kristopher ryan says:

    you are right on the money with this, sean.
    it is unfortunate that people want to be an entrepreneur, or start a start up of their own merely on the basis that they think they should because everyone else is. it is far more than this.

    you have to have passion..for something. and all of us should, as responsive human beings. for those that don’t, there is no way becoming an entrepreneur, your own boss, or a founder of a start up will ever be feasible for you simply because you lack that fundamental spark. And therefore, maybe you deserve to slave away at your 40+ desk job working for someone else. unless, of course, you’re cool with that.

    I know i certainly am not.

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