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Hey Chris and other Tangentialistas,

I’ve been pondering this for a long time, but more recently it has become a persistent focus of mine in relation to my current job.

The question is: How do you know when to leave something good?

My current job is great in many ways, I get paid well, I like my team, I believe in the value of the work we’re doing, I’m excited about our company’s future, and I’m excited about our mission and core values. That being said, the daily responsibilities of my position are intellectually engaging but make me feel emotionally neutral at best, and they are frustrating or anxiety-inducing at worst. In addition, I’ve been working more than I would like and have had little time to see my friends or take the weekend trips I’ve wanted to take. I suppose this is the trade-off of a start-up job, and I understand how important the experience will be for the rest of my life, so I think I’m willing to make that trade. But this persistent feeling that it is not enough has been circling my mind for the past year. This job and the opportunity of gaining this experience is pragmatically important, but it goes against the emotional and psychological signals telling me to do something else. I came into this job with very little “professional” business experience on my resum√© so I’ve held on to the job.

But back to the question. How do you know when to leave something good?

Do you have any advice or thoughts on this? When does it become clear that a person should make the choice to leave something good based on a feeling, without any logical or rational explanation to back it up? Most of the hardest choices I’ve ever made fall into this category, but I still don’t have a good method of evaluating these decisions. I usually get tied up in knots for months just trying to reconcile the mismatch between my emotional response to a situation telling me to leave, and my rational mind telling me that I need more evidence to support the decision. I do believe in following my gut, and in this situation that may be less logical in terms of professional experience, and it may mean a more “difficult” journey forward, but maybe I just need to believe that the emotions are there for a reason and they will guide me to a better future that is more aligned with who I am.

For context, I’m a 26-year-old guy and I graduated from college two and a half years ago.

I think the secondary question here is: Should I keep the job and make the most of this unique and important opportunity to gain experience running a business, or should I leave the job so that I can prioritize taking advantage of the unique possibilities and qualities of youth?
On another note, I have a pretty good idea that I want to spend my life making art, doing design work, and building things. The idea is to gain business experience from this job and put that to use in my future design/build business, in addition to saving money from this job to fund my future design endeavors.

I appreciate any and all feedback on this. All the best to all of you.

Thanks for everything you do, Chris.