Should you start a side hustle?

It's an easy question, with a tough answer.

After my recent post about the dark side of starting new things, a friend asked me to write a little about starting a side hustle. As it turns out, I’ve been thinking about this a lot over the years and have a lot to say on the subject. But first, let me set the stage.

What is a side hustle?

A side hustle is generally agreed to be a way of making money “on the side” of your current work. It can be anything from freelance writing to coding to owning real estate. There has also been a TON of writing on this subject by best-selling authors and hopeful writers on “how I make $xx,xxxx a month writing blog posts” that I personally find unhelpful.

Most of the talk around a side hustle is about how you need multiple income streams to be wealthy (whatever wealthy means) and how you need to work obscene hours to get there. I love the idea of multiple streams of income and despise the idea of working insane amounts of hours, sacrificing your family, friends, and personal well-being.

I started the agency that I sold a decade later as a side hustle. And I have a couple of side hustles now, in addition to my full-time work leading marketing for a fast-growing nonprofit that does amazing work.

Questions to ask before starting a side hustle?

  1. Why do you want to start a side hustle? What’s the end goal here? You won’t know if you hit your goal if you don’t set one from the start.

  2. What kind of time are you willing to dedicate to this? A side hustle does take time. And, while I believe it can be done without overworking yourself and sacrificing family time, you will have to make some sacrifices, so what are you willing to do without?

  3. What boundaries will you set up to guard what’s important to you? Having clear boundaries of time and focus are critical so that your side hustle doesn’t consume all your life.

  4. How will you know when it’s time to turn your side hustle into your main hustle, if at all? Make sure you set up some goals and know when you will be willing to make the move to making your side hustle your main thing, or if you ever want to do that at all.

So, should you start a side hustle?

If you have the time, passion, a solid plan, and clear boundaries, I think a side hustle can be good. But bear this in mind. To do anything great, anything worth doing, requires focus. As I’ve mentioned before, focus isn’t my strong suit, but I realize more and more the role it plays in success. By definition, a side hustle removes your focus from something else. So, with that in mind, I recommend being very clear about your desired outcomes and be sure the division of your focus will be worth it in the short and long run.

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