Nine metrics to use to evaluate if you should take on another side-hustle project

Or how to avoid dying at 40 from stress and constantly being ‘busy.’

Back in 2011, I hit at a breaking point in my life and needed to make a change. I’d took on too much across all my professional work, a fellowship studying mobile tech, co-directing the Society for News Design’s St. Louis convention, co-directing the NPPA Multimedia Immersion, working on the board of the Online News Association including several committees and as Secretary of the executive board, freelancing, plus more than two dozen speaking and teaching engagements.

My health, stress and general well-being was way out of whack and I had to start making life changes and being more selective about what I take on, saying “no” to some opportunities. It took a couple years to wind things down and become much more selective (and I still fall back to my old ways and overload myself) but I developed a checklist system for evaluating projects.

I was reminded of this list last week at the 9th annual Multimedia Immersion (yes, this is one of the few things I didn’t wind down, yet) when the amazing, humble and world-famous photographer Greg Heisler was speaking on stage during our freelance/career discussion. He said he had a handful of tests/motivation points for making decisions about when he would pick up work and relayed some stories where he took less than the money he should have received for the opportunity to work with cool people or for future gigs.

Here’s my list that I developed (in no particular order) for deciding if/when to take on extra side-hustle projects:

• Skills — To learn new skills.
  (It’s important to be constantly evolving your skills, living the kaizen way.)
• Impact — For the impact it makes on the world, to do good.
  (I’m starting to be much more critical about what real and exponential impact some work can have and trying to find bigger/harder/more impactful things to take on after reading “Bold.”)
• People — To be around and work with amazing people.
  (As many people say, ‘You are the average of your 5 best friends,’ so finding more awesome people to influence you and raise your awesome average is always good.)
• Money — For the substantial money.
  (As in $100/hr rates or as an investment that will likely have exponential returns.)
• Challenge — To be challenged, solve interesting problems.
  (This can take many forms and be a dangerous one because some challenges can consume you if you take them too far, but accomplishing difficult things can be very rewarding.)
• Pleasure — For the pleasure/calling of doing the work.
  (Some things like maintaining a garden or brewing your own beer, may not be lucrative or extremely productive uses of time, but there’s a personal pleasure you can derive from the experience.)
• Resume — For the future career opportunities that will grow from this.
  (Sometimes this is hard to gauge since it’s hard to know when a connection to make helping with a conference could lead to a job, but the line on your resume is a little easier to quantify.)
• Reputation — To build character and status.
  (Especially building a reputation of serial start-up successes, so that when people think of you they know you’ll deliver and are good to your word.)
• Appreciation — To feel appreciated.
  (Although this frequently doesn’t happen easily, openly or very clearly, so this should not be the primary motivator.)

Not everything I decide to take on has to hit all these points to get the green light, and some things might just be incredibly high value in one or two, but ideally, I try and only take on work that fulfills at least half of the items on the list.

If I work through this checklist and I’m still on the fence, I sometimes consider what a (soon to be former boss) Rob Bole, said something at a BBG staff meeting encouraging us to innovate and push the boundaries (which I have had scribbled on a Post-It note on my desk wall since): “When you have the choice between two different options, choose the most dramatic.” New adventures stretch and grow your character and experience more than doing lots of the same thing year over year over year. Choose those.

(This post originally appeared on Kaizen Will, a side-hustle project on how to live a more awesome life of constant improvement.)