Side Hustle Hurdles

I realize that it has been a long time since I have written about my favorite activity.  The truth is, it is hard to really define what a side hustle is anymore in my half retirement.  Hospice work, which started as a lazy side hustle, now has become my main hustle.  And blogging and podcasting, also mechanisms of collecting small incomes, feel more like my passion and purpose.  That being said, even in financial independence, there is still room to pursue some of these alternative gigs.  The barrier to entry, however, is greater in the sense that I am less likely to add a new activity unless it really brings value to my life.  In other words, there are a number of side hustle hurdles that now exist.

To engage in any new, possibly revenue generating activity, a number of criteria have to be met.  Although it is easy to say that this luxury is a result of financial independence, I think I have mostly kept to these principles throughout my career.

Hurdle 1: Joy

Put most simply, a major side hustle hurdle is the suck factor.  I don’t care how much money I can earn, if I dread putting the time in to make this hustle work than it is not worth it.  Telemedicine is a perfect example.  For about a year I had a part-time telemedicine position.  While the practice itself was not so bad, between getting my licensure settled in multiple different states and the unpredictability of schedule, I was no longer having fun.

Although not sucking is part of the equation, the other more important issue is the joy.  In almost every side hustle that I have ever done, I have always searched out the opportunity to derive pleasure from the activity.  Whether it was building an art empire or real estate, if there was no opportunity to enjoy the process, I wouldn’t start in the first place.

Hurdle 2: Upside

While being financially independent makes money less important, a major side hustle hurdle is scalability and upside.  While being an hourly employee is fine, I look for opportunities that could blow up one day.  Why?  Again, the possibility of riches is only a small part of the thought process.

I am a sucker for the idea of building something durable and elegant.  I lose all interest in a side gig if I see it as limited or unable to grow into something more grand.  There is joy in the process of thinking big and daydreaming.  Half the fun to any side business is pondering the heights that are there to climb.

Hurdle 3: Non Economic Benefits

Even if you are looking to create an important stream of revenue, I think the lack of non economic benefits should be a major side hustle hurdle.  In other words, your side gig should provide a lot more than just income.  Some of my best side jobs have brought not only a paycheck but also new relationships, knowledge, and outlooks on life.

My medical expert work introduced me to the legal world.  My art business taught me how to buy and sell online.  Writing a book introduced me to an editor and a good friend.

Sometimes it is the intangible benefits that last far longer than the money collected.

Final Thoughts

Although being financially independent changes the way I see the process of making money, I think the joy and pleasure of side hustles remains.  There are, however, side hustle hurdles that need to be overcome before I think an opportunity is worth my time.

These hurdles have always existed even before my financial footing was stable.  And for the most part, I think I overcame them in most of my activities.

How about you?  Are there any hurdles that keep you from doing a side hustle?