My Framework for Figuring Out if Entrepreneurship is Right For You

By Sean Ogle •  Updated: 05/21/14 •  5 min read

This started off as a post about excuses.

However, once I started writing it, I realized there was an entire blog post I needed to write before covering how to overcome your excuses.

What is that you might ask?

You need to understand why you want to start a business in the first place.

If you email me and say “I’m ready to start a business” and I ask you “why”, and you don’t have an extremely clear answer to that question, then you’re not ready.

Often the people with the most excuses are the ones who shouldn’t be building a business to begin with. So how do you figure out if entrepreneurship is the right fit for you?

Three Step Process for Figuring Out What You Want

There are a few questions I’ve learned to ask people who aren’t totally sure what they want. These 3 questions won’t be the answer to all of your problems, but I bet they can help crystalize a few things you may have been struggling with.

1) What Do You Daydream About?

When you hear the word daydream you might get visions of a sappy little 12 year old girl with her first crush. But the reality is, we all daydream from time to time, and understanding where your mind wanders during that time is key.

I could ask you “what do you want to spend your days doing” but that’s usually when people say “uh, I don’t know”.

Thinking back to your daydreams, that you may not even consciously acknowledge at the time, helps you to figure out what you really want deep down. As I’ve mentioned multiple times, I used to pretend I was running on the beach during my lunchtime runs in Portland. I’d imagine just outside my office was a beautiful ocean – it was clear to me that I wanted to travel, and that I wanted the freedom to do it on my own terms.

For others, it could be daydreaming about being able to stay at home with your kids and not having to pay for child care.

By doing this, you’re giving yourself something to work towards – a goal, a reason to make it all worth it when things get difficult (which they will).


ABOVE: This is the coconut that changed my life. I was sitting on Copacabana Beach drinking it, and that’s when I made the decision once and for all that entrepreneurship was right for me.

2) Why Do You Think You Want a Business?

If you’re thinking of starting a business because you’re struggling to make your rent every month and you need to make some fast money – then I’m sorry, but entrepreneurship may not be right for you – you have bigger, more immediate problems to address.

If you want a (lifestyle) business because you’re unhappy with your current situation, want more freedom, and are doing work that’s unfulfilling then you may just be on to something.

Also, if you’re only in it for your ego, stop now.

You might have heard the statistic that you get 90% of the satisfaction for just saying something. As an example, when I was working on my beer importing business, it made me feel really cool and accomplished to tell people I was importing craft beer into China.

Even though in the end, I never imported a single bottle of beer into the country, all I had to do was talk about it and I got a huge ego boost.

I see that all the time, and it can be difficult not to. You talk about all the things you’re going to, get the ego boost, and then never follow through. Really think hard about why you want to start a business. If it’s mostly so you can say you own a business, then you’ll get a big ego boost, but in the end you’ll be right back where you started.

3) What Type of Work Do You Like Doing?

Notice how I don’t say “what are you passionate about?” All of that follow your dreams and turn your passion into a business crap will come later. At first you need to make money.

So what do you like doing?

If you hate writing then obviously you’re not going to want to start a blogging or freelance writing business. Do you like sales and being persuasive? Are you more of a hands on tech person? You should build a business that allows you to at least do work you don’t hate. I’m not saying it’ll be the sexiest job right away, but you don’t want to dread working on your business.

Putting it All Together

Simply put, if you don’t know why, you will fail.

The goal of these questions is to help you answer that questionWhere do you want to go, understand the reason, figure out how you’ll get there –  that’s the formula, if you can do these things you’ll have a much clearer understanding of why you’re starting a business.

If you’ve gone through this exercise and decided a business is right for you, but you still haven’t pulled the trigger, stay tuned for our next post.

Still not sure? Leave a comment, and we’ll help you work through it!

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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20 comments on "My Framework for Figuring Out if Entrepreneurship is Right For You"

  1. Good stuff Sean, thanks. I thought it was great how you distinguished work we like doing versus what we’re passionate about. Definitely a difference there and an important one. I daydream often about traveling to where I want, when I want. I want a business so that I have a platform that will help me make a positive and lasting difference in the lives of others. I love writing, connecting with others, and seeing them happy and succeeding. That’s my three all put together. Thanks again for your words, always so helpful and inspiring. Cheers!

  2. Enzo says:

    Interesting read, I’ve always been day dreaming about my passion and hobby, which will hopefully help me get to my goal of being location independent! Thanks for all the help you’ve given me so far!

  3. Erika says:

    Lol I just realized I frequently daydream about growing my blog and coaching biz – I am a nerd. Sometimes I daydream about where we will travel to next – at least that is kinda cool.

  4. Christian LS says:

    Awesome post Sean.

    Really does get those who are unsure to take a step back and rethink their purpose to the underlying truths in the first place.

    For me, it’s to have that freedom of having no clouds over my head.
    Can’t wait to start traveling again unbound by nothing but my own limitations.

    PS. I’m pretty sure that coconut was drank at Ipanema, but close enough 🙂

    1. Christian LS says:

      PPS. Actually I’m positive that’s Ipanema judging from the tiling on the ground.

      Anyways, I can’t wait to get back their 🙂

  5. Scott Asai says:

    The “why” is so crucial towards being an entrepreneur. It has to drive you in the midst of uncertainty. For me, it’s always been for freedom and flexibility of schedule. Now with a child, it’s intensified even more. My wife and my daughter are my motivation for working hard. I love coaching and that’s part of what I do, but when it comes down to it, I think it’s about hustling to get paid doing different things. I’ll never stop learning, growing and re-inventing myself. It’s a challenging journey, but one I hope I’ll be on for the rest of my life!

  6. Chris says:

    Great post Sean, I’m realizing that the more I put ideas and doubts down and the more I actually take action on them and obtain results!

  7. Its really important to do this sort of thinking when it comes to going into business. Spending the time to think about what you really want and where your heart is can really save you trouble in the long run.

  8. Patrick Wong says:

    Can’t agree with you more, Sean. The stronger the “why”, the greater your chances of succeeding in the venture. You just have to keep grilling yourself with the right questions to get compelling reasons before you start. Once you have the answers, just get going.

    Thanks for this reminder.

  9. Ana says:

    Great thinking, Sean. This is something I’m finding I have to stop and think about more. As much as I wanted to go into business for myself before, because of the recent crisis which hit me hard, now it’s even more important.

    I find that doing something like starting a business just to avert future disaster is not enough of a reason to do it. I’ve wanted it all along, long before anything bad happened. I just didn’t have enough self-discipline to get to it. Now the why is paramount. I’ve answered the questions. I take great joy in finding my answers are the exact same ones I gave myself a dozen years ago. I want freedom. I want the freedom to live wherever I want and travel where I want and that means enough money and no worries about money.

    So I’ve started. Now comes the hard part — continuing.

    Thanks again, Sean!

  10. Chas says:

    I think the word ‘entrepreneur’ often gets bandied about too often these days. Many times when you get to the core of what a person really wants, it is just a simple small business doing something they love to do. The illusions of ‘being your own boss’, time-freedom, and a fat paycheck often don’t match up to reality. Often the climb is harder than it first appears.

    1. Chas says:

      Guess I said often too often, but, it’s too late to edit.

  11. Joseph Dabon says:

    Nice three-point tips. But there is lot of things to consider before becoming an entrepreneur. Natural bent for it, is one crucial factor to consider. Entrepreneurs are a bad apart from ordinary mortal.s

  12. Martin says:

    I just wanted to add: hating your job or the idea of work isn’t a good enough reason to want to be an entrepreneur. You might just need to switch jobs.

  13. Jeff says:

    Thank you for this! Great read and great points! Thanks again!

  14. Jan says:

    Sean, thanks for this great post. Makes me think and wonder if I have thought way too small about if I am capable of entrepreneurship which is my greates fear. These questions help me move forward.

  15. Steve Roy says:

    It’s been a long while since we’ve touched base!! It looks like you’re doing well. Your point about getting an ego boost really resonates with me. For me, it was my job. I was a financial advisor with a large and well respected brokerage firm and the idea of having the job was far more interesting than the actual job.

    I got a huge ego boost telling people what I was an FA and part of a $200 million business. The problem was that I fucking hated the job. In the end, I decided that I’d rather be happy in a less prestigious job and be happy. So that’s what I did!

  16. Ana says:

    Just one thing to add to the entrepreneurship debate — if it’s indeed a debate: These days, for many, becoming an entrepreneur is less of a choice and more of a necessity. “Switching jobs” is an idea with less currency now than at any time in modern history. There simply aren’t enough jobs to go around anymore, and there never will be again — certainly not for someone hitting 60.

    So my other reason, besides what I so very much want, is that I simply have to. I have no other choice.

  17. Ana says:

    I wish I HAD a choice. I am still employed but after a year and a half it’s still under temporary status and that’s nerve-wracking. I hit 60 in less than 2 weeks and this is one milestone that’s not considered positive in the employment realm. But as an entrepreneur … not bad at all! I get to parlay all my life experience into this business which actually will combine 2 types of services and some products. I’m wildly excited about it and the possibilities! Oh, I don’t expect to make a bundle straight away but I’m heading towards independence. There’s NOTHING (except friends, loved one, et al) more important than that! 🙂

    All the best to us all!

  18. Steven James says:

    Great post, you kept it simple that allows clarity. I’ve been day dreaming for a number of years, around stock market investing and starting an ecommerce business. Have tried both part time without much success, and I just need to bite the bullet and go full time and trust that it will all work out fine.

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