What would you say to a new Entrepreneur about why you chose the entrepreneur lifestyle?


Several of my friends want to become entrepreneurs and they always ask me what draws me to it. For me, it’s the freedom to create, seeing that what I do really matters and the focus on building innovative products instead of feeding the corporate bureaucracy (a la TPS reports).


asked Dec 6 '09 at 09:36
Jarie Bolander
11,421 points
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6 Answers


What makes it something I am involved in:

  • I have felt like I was stagnating at many jobs. While I love coding, I also like to get involved with customers, business development, QA, etc - all the things involved in a business. I don't want to be just a cog in a large machine.
  • I prefer to work for myself - though i realize that may mean more hours than a typical development job. I want to see the direct results of the work I do.
  • I was sometimes a bit too contrarian or critical at the places I worked - sometimes this was taken the wrong way and I was not seen as a team-player
  • "The Millionaire Next Door" is pretty clear about the studies of wealthy individuals - you do not become wealthy (typically) by working for someone else. You have a greater chance of success by starting your own business.
  • I want the freedom that being a successful founder and business owner gives (After putting in all the years of hard work) I don't want to slave away for 2 to 4 weeks of vacation until I am 60 - I want the opportunity to work when and where I choose and perhaps have a chance at retiring early - that does not happen in most typical employee scenarios.
  • I wanted to run a business my way - and do things right - not be told that my feedback was unwelcome or that policies could not be changed (For example real vacation policies - 5 or 6 weeks rather than 2 or 3, offices rather than cubicles, etc)
answered Dec 6 '09 at 15:37
Tim J
8,346 points
  • I like the variety as well. There is something about seeing the whole life cycle from concept to sale that makes you feel like you built something useful. – Jarie Bolander 14 years ago


It takes a lot to become an entrepreneur. The most important i would say is the ability to take risk! It is very easy to be a top architect or a top executive in a big company, drawing a handsome package than doing something of your own. The most important motivation of an entrepreneur is the confidence he has on him self and that gives so much satisfaction to an individual. The other important aspect is freedom. So there are so many great things that drag people to become entrepreneurs. The last and not the least is the satisfaction factor !!!. Satisfaction of believing myself and eagerness/daring to do something of my own

answered Dec 6 '09 at 15:17
88 points
  • Confidence in your own abilities is so true. If you lack that, I don't think you can successfully zig and zag when things go wrong. – Jarie Bolander 14 years ago


I think it's about being able to call your own shots and having more control over your life. No matter how nice my managers were, it still didn't feel quite right that someone else was telling me what to do, and I was working towards somebody else's goals. And that's even without getting into the incredible corporate wastefulness and inefficiency.

That said, some people prefer the sense of structure and security (which is false in my opinion) that they get from being an employee. Other people like not having too much responsibility and working a fixed number of hours.

In the end it's really a matter of what feels right for you. If can't imagine working for someone else for the rest of your life, then it's probably worth trying to strike out on your own.

answered Dec 6 '09 at 11:42
Alex Aotea Studios
665 points
  • The big company security excuse is one I hear a lot from friends. I agree that it is totally false and you are less secure being pigeon holed at a big company. – Jarie Bolander 14 years ago


Can you "become" an entrepreneur? My experience is that people are or they aren't. Some people are and are in positions that don't make give them the flexibility they need. My first job was at a 100,000 employee defense contractor but I never fit it. I was constantly trying to change the way things were done, trying to make things better. People never understood why I could not just go with the flow. The day I started at a startup I no longer felt like a square peg in a round hole.

I think people need to look at why they are dissatisfied with what they are currently doing and figure out whether starting their own business, or joining a startup, will fix it. I agree with you that the freedom to create is my driving force. For others it's the flexibility and the ability to have an impact.

They have to be honest with themselves though. I often hear people attracted to the "buzz" of being an entrepreneur but they like all the services provided by a big company and they like that they get to focus on their small specialty and don't have to do other people's jobs. Those people don't do well in startups.

answered Dec 6 '09 at 11:46
1,866 points
  • I think you can become an entrepreneur but it does take a certain attitude that some people just don't have. Being true to yourself seems like an important piece of choosing the entrepreneur lifestyle. – Jarie Bolander 14 years ago


I have had my own business as a public accountant for going on thirty years. About 13 years ago, I cut way back on my business so I could go become a programmer. I worked for a great company that had several very large clients. I learned a lot and I enjoyed the company of peers for a change. One thing about being an "entrepreneur" is that everyone else who works at your business is an employee. It's a very different relationship, whether you like it or not. It was nice having peers for a while.

After a while though, I found that I really did miss dealing with the heads of other businesses. Even if a person's business is small, it's a special thing. Some people risk a lot to fulfill their dream. As a CPA, a lot of times my job is to help them keep their feet on the ground even while their head is in the clouds.

So I'm back in public accounting again. Only this time there's a twist. I'm developing my own app that I hope to sell to other accountants and small businesses.

One thing you should keep in mind is that risk is highly overrated. The best small business people do everything they can to eliminate risk. Also, much of the business of having your own business is about doing things that are not the things you love. If I can refer you to a book, I would recommend The E-Myth or The EMyth Revisited . Personally, I liked the first one more.

answered Dec 9 '09 at 04:21
Jack Rodenhi
607 points
  • Thanks for the insights. Sometimes being an entrepreneur is a lonely thing. Good point. – Jarie Bolander 14 years ago


  1. Wealth creation
  2. An ability to deal with banging my head against the wall day in and day out. For years.
answered Dec 6 '09 at 15:21
659 points

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