5 Reasons Why and 5 More Why Not to Start Your Own Business

This post started with a conversation I overhead while walking on a sidewalk. I didn’t want to hear it, but they were very loud. I’ll spare you the details. It did get me thinking about these two lists: first why, and then why not to start your own business.

First, a note about the outcome and the impact of the outcome. You don’t know for sure, as you start the process of building your own business, how it’s going to turn out. I’m sure that all of us would rather jump into a time machine to a few years in the future, look at it then, and use that to decide. But we don’t get to.

That is why you want to plan that business before you start. Not the big formal document necessarily, but definitely the plan, with strategy, milestones, basic numbers, cash needs, and a review and revise schedule. The plan reduces the uncertainty. If the planning process turns up real problems, and stops you from starting a bad business, then it’s done you a big favor.

Beyond that obvious fog-of-war blindness about the actual future, here are five good reasons to start a business:

  1. People need or want it. Are you filling a void? Do people really want what you’re selling. How cool is it to provide something that makes people feel better, sleep better, learn better, live better, and so forth.  Look at some successful startups, and they were built around things that made life better: computers, transportation, web applications, organic food, tutoring, a whole world of new and better things and ways to do things.
  2. You’ll be better off.  This spans a wide range of situations, from making more money, to sharing home and child time, to living in a better place, having more time; this is such a fundamentally good reason that it spills over to the others to follow. And don’t forget your relationships, as in family and loved ones: don’t think you’ll be better off if they aren’t. (Or if that sounds good to you, do you and them a favor and get out of that relationship).
  3. You’ll be happier.  For me, looking back, one of my main drivers was wanting to do things my way, wanting to spend my time on tasks that interested me. I wasn’t sure I’d make more money or make my family better off, but I was pretty sure I wouldn’t make less, and they wouldn’t be worse off, while I would be doing something I liked and believed in. I’m not the only one.
  4. You’ll control your own destiny. When you build your own business, success or failure depends on you, not your boss, your company, and much less politics or being a team player. I’ve always liked that feeling myself. I’m pretty sure I’m not the only one.
  5. Change the world for the better. Build a business, employ people, give them something meaningful to do, and you make the world better off. Is it possible this is the same satisfaction that you got from building a sand castle on the beach, when you were a kid, except longer and stronger and more real? Not to be dramatic, but starting a business, if it lasts, adds something to the world. More so if the business has a purpose

And, on the other hand, once again suspending the critical point of whether or not it’s going to be successful (plan it well, please), here are five reasons not to start that business:

  1. It takes a lot of work. I’ve been dealing with entrepreneurs for more than 30 years now, and I’ve never seen even one of them who worked less while building a business than when he or she was an employee, or a student, or something else.
  2. It causes a lot of worry. It’s hard to avoid. You don’t know the future, you live in uncertainty, and, if you grow, people depend on you. You take risks like credit lines and money owed to you and money you owe. You spend money based on future projections. If you’re Zen enough, maybe you don’t worry; but most people do worry. There’s a lot of stress.
  3. Failure can cost you big time. Businesses do fail, and not always through the fault of the owner. Even good decisions have bad outcomes. There are a lot of factors you can’t control. I know people whose business failure cost them their sense of self, plus their life relationships. If you can’t deal with the possibility, don’t go there.
  4. You won’t be your own boss. It’s funny how often we equate owning your own business with being your own boss. That’s only partly true. You do get the independence I mentioned in number 4 above, controlling your own destiny. Usually you can set your time schedule, and often even your customers. But consider this: you’re not your own boss; your customers are your boss.
  5. You will make mistakes. If you can’t live with mistakes, don’t start your own business. You’re doomed. You can’t go through this forest without making some wrong turns. The good news is all businesses make mistakes, and most of them survive them. But if you can’t live with your own mistakes, keep your day job.

Conclusion: this question of whether or not to develop your own business is yet another of these questions that get answered poorly, with a lot of generalizations. It’s a matter of pattern recognition, planning, work, and knowing who you are and what you can do and what you see as a successful outcome.

It’s not for everybody. Is it for you?


  • Kirsten says:

    This is such a nice, straightforward summation. In its simplicity it fosters clarity, which is so helpful when you are starting a business and, with so many decisions to make and new info to negotiate, need things made as simple as possible! (Atl east thats the way it is for me).

  • Case Management News | Case In Point Weekly says:

    […] The Pros and Cons of Going Out On Your Own […]

  • Louis E. says:

    This article got me to think on my recently started business. During my 30 years as an employee, I always thought I could do this on my own and make more money. Don’t get me wrong, I knew they would be challenges and would not be easy. Been an armed forces veteran, failure is not an option and I sometimes fear of failure but won’t know a failure if I don’t try. However, as in the military and my former employer, I need a plan.

  • Harry Vaishnav says:


    Excellent points. Many people underestimate the amount of work needed to be their own boss and end up getting frustrated or, even worse, losing money when things don’t turn out the way they had thought.

    On the contrary their are others who are afraid of getting into independent business even though it will make them lot happier compared to corporate life.

    My advice to all those who are thinking about it is to understand the pros and cons of both sides of the coins and make an informed decision so that you won’t regret it one way or the other.

  • Trinity says:

    Excellent post. Great insight.

  • Ken says:

    I learned a long time ago that in order to be happy in life you must take risks. Risk going to college, going into the military, trade school, or working at McDonald’s. Risk getting married, having children, making a career move – or not. Buddha said “It is better to travel well than to arrive.” I believe it is better to try what will make you happy. Don’t worry about a failure or success. If you are doing what you love to do, you will be happy. Oh…and write a plan.

  • Himanshu Chanda says:

    Definitely Tim as you highlighted its more about pattern recognition. The only answer to the question whether I should start a business is – “Well, it depends”. And it depends on us more than any thing else. Once a person knows himself clearly and knows what he really wants… I guess he is ready to take the plunge!

  • MsSmallBiz says:

    Fantastic article! I think it is really important to weigh up pros and cons and this would help anyone looking at starting a small business. Well done!

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