Working For Yourself is Exciting and Scary

I was reading a pair of articles referred to me (indirectly, it was via Twitter) from a friend and colleague at Insight Council. The articles, “Should You Be An Entrepreneur?” by Daniel Isenberg, and the rebuttal “20 (More) Reality-Checking Questions for Would-Be Entrepreneurs” by Seth Kravitz, were both interesting. What I found, though, was that the list of questions to test your suitability as an entrepreneur were far too long, with many of the questions being repeats of themselves. Isenberg’s article focused almost exclusively on the positive, and failed to mention anything even remotely “negative” about the entrepreneurship experience. The Kravitz piece was basically negative, looking at all the scary things that come with running your own business. Taking both together is more useful, but again, having to ask 40 questions seems a bit much.

So, what would I change? What is my list of questions? Having been something of an entrepreneur off and on for the past 20+ years, here are the questions I would ask. I have posed some of them to friends who have considered going into business for themselves.

  1. Do you like to be in command, to be in charge, making both big and small decisions, all the time, every day?
  2. Are you always looking for a better way to do something, or are trying to solve other people’s problems?
  3. Are you multidimensional, being able to handle different disciplines (technical, administrative, sales/marketing, support), but are not necessarily an expert at all of them?
  4. Do you recognize when you are weak in an area, and have the sense to ask for help?
  5. Do you handle risk and uncertainty well?
  6. Can your family handle risk and uncertainty, or at least trust you to handle it?
  7. Are you prepared to put in long hours, handle all tasks (including the tedious ones), even when it may be inconvenient for you?
  8. Are you prepared to accept the outcome and consequences of what the business does, good and bad?
  9. Are you prepared to give up control to be able to build something bigger?

That’s it. These are the questions I have asked myself, and that I have asked others, when considering being an entrepreneur. I believe that you have to be able to answer a confident and unqualified “yes” to the first 8, and “yes” to #9 if you want a bigger payout, or want a bigger business.

Answering “yes” doesn’t necessarily mean you really can be an entrepreneur. What it means, in my mind, is that you have the potential, and that you could at least give it a try. Many of the things covered in those questions can also be apply to being an employee of someone else’s company. The difference is that you’re not necessarily the one at the very top of the org chart, or the one holding the most shares of the company. The company isn’t “yours” in both the psychological and physical sense.

Now, there are a supplementary set of questions I would also consider when looking at going into business with partners (be they family, friends or professional colleagues). The questions above are fine if you are doing something on your own. But, if you are going to start a business with a group of people, there are a few other questions that need to be answered.

  1. Can you reliably predict how your partners are going to react to any given situation?
  2. Can your partners reliably predict how you are going to react to any given situation?
  3. Can you trust any one of your partners to take charge of something, and believe they will do what’s right for the company, and not just themselves?
  4. Do your partners trust you to take charge of something, and believe you will do what’s right for the company, and not just yourself?
  5. Do all of you have the same goals (personal, professional, financial) in mind?
  6. Can you risk losing the relationship you have with your partners?

I believe that you have to be able to answer “yes” to all of these. Basically, the questions are around whether you trust your partners and know them well enough to predict what will happen in good and bad times. They also need to know you well enough. The trust doesn’t have to be unqualified and absolute. We all have our weaknesses and foibles. The point is to be able to predict what they’ll do, not that you agree with their behaviour. If you know one of your partners is going to react in a certain way to a situation, and that reaction is bad, then you do what you can to avoid that situation or know you have to somehow deal with the behaviour. While we would like to think that all partnerships should be “all for one, and one for all”, the reality is that it is “all for one, and one for all, except….”. Being able to live with the “except…” part is key, provided you can see it coming.

A partnership is also about understanding each other’s strengths and weaknesses, and being able to “fill in the gaps” as well as enjoy the overlaps (and not see it as competition). Being able to work with people you like and trust (or at least can predict) can sometimes result in something bigger and better than if you had tried to do it on your own. If your partnership is multi-disciplinary, then it also means less pressure for you in some areas. For example, if you are largely a technical person, and one of your partners is more in the sales and marketing side, that gives you the ability to focus on your strong areas. However, it also allows you to learn, first-hand, more about other areas of the business and be able to get involved in them directly. That can be hard when you work for someone else.

Being an entrepreneur is both scary and exhilarating. It isn’t for everyone. You may find that, even if you answered yes to the first set of questions, it still isn’t for you. Before anyone jumps into a new business, I think they need to think about those questions, and be honest in their answers. Owning your own business may look inviting, but it isn’t for everyone. It has some downsides, but if it is something you are truly prepared to commit to, it can be very rewarding in many different ways.