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Adii Pienaar

Now working on Receiptful. Co-Founder & ex-CEO of WooThemes. Author of Brandiing. New Dad. Ex-Rockstar.

Should You Start A Company?

Maybe.

I'll be the first to admit that I don't know the answer to the question and my best response is "maybe". Not because I'm non-committal, but because any answer to that question is much more nuanced than anyone would suggest.

Aaron Hillegas' "Don't Start a Company, Kid" touches on a whole bunch of reasons why you probably shouldn't start a company (and instead seek employment at an awesome company). For every Aaron Hillegas though, I can find at least one other, successful entrepreneur that will persuade you to instead work on your own startup and definitely not seek employment of any kind.

Both sides of that coin is valid and both would probably make sound decisions were you to make them. But saying that only admits that we're between a rock and a hard place on deciding whether we should or shouldn't start a company.


I have a slightly different take on the thought-process about whether you should or shouldn't work on your own startup. Here's a couple of my considerations:

  1. Do something for youself. Be selfish in your decision: what are your needs? And how would starting a company or taking up employment satisfy those needs? Want to be challenged to create something of your own, then work on a startup. Or you want to contribute to an effort that is already profitable, then seek employment.

  2. What's the underlying passion & motivation? This probably touches on being selfish, but you should know who you are and why you want to make a decision either way. Ultimately you have to live with whatever decision you make, so try make the decision that is the truest reflection of who you are and who you want to be.

  3. Who are you doing this for? I recently realized that I wasn't willing to work 120-hour work weeks, as that would severely compromise on the time I'm able to spend with my family & friends. The former is very specifically one of the reasons why I want to be a successful entrepreneur: I want to provide for me family. But at what cost does that decision come? And what does my family really want from me?

  4. Define what your success will look like. Before you start on anything, have a clear idea of what would or wouldn't constitute success. If the only way for you to feel successful is to sell a $1bn company to Facebook, then you're unlikely to ever feel successful being employed. Or maybe you're happy being an early employee with a 5% equity in something that eventually earns $10m a year. Whatever it is, know what will make you feel succesful and pursue that.


As much as entrepreneurship could be for everyone, it just isn't for everyone. And importantly, there's nothing wrong with that.

Nobody else can tell you whether you should or shouldn't start a company. I think this is a deeply personal and intimate conversation that you end up having with yourself about your preferences, your desires, your appetite for risk and perception of what work+life looks like. That in itself will render a very unique blend from one person to the next.

Figure out who you are and then decide whether you should start a company.


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