Confident decision making is one of the hardest lessons to learn. In part, I think this is because we spend so much of our lives outsourcing decisions to other people.

It’s also why the “advice industry” is so freakin’ huge – and I say that knowing that Amy and I are a part of that industry!

I wanted to share an exchange with one of our students where the best advice I had was: “Don’t take this advice.”

“Halp!” they shared in our student chat room. “I need a reminder why I’m in here. I’ve been offered a job that is really really cool, but I have fear around being an employee again after 10 years of doing my own thing the 30x500 way.”

After a few fellow students offered encouraging words, I asked how we could help, and if there was anything specific they were hoping to hear from us.

They responded: “To keep charging ahead.”

I paused to think. Here’s what I said.

I don’t want to tell you to keep charging ahead, nor do I want someone else to tell you that, because I think it would be irresponsible for you to listen to advice given with near-zero context.

“Ahead” is relative to the direction you’re pointed.

Someone can easily tell you “charge ahead” when you’re pointed in the wrong direction, and not know it.

So context matters a lot for a decision like this!

  • Is this a job you want, or a job you need?
  • What are the upsides to this potential job that would be extremely difficult or impossible to get on your own?
  • What are the downsides of this potential job, outside of taking you away from your 30x500 work?
  • Would this job force you to halt your 30x500 work completely?
  • Could you negotiate an arrangement that let you have the best of both worlds? the upsides of the job, but retain whatever parts of your 30x500 work you care about most?

There isn’t a single right answer here, or even a single meaning to “keep charging ahead.”

Instead of thinking about a job as a step backwards (which you haven’t said but your comments do imply), is there a way you could use this job as a tool or leverage…instead of feeling like it’s using you?

I’d take a step back and think “what does ‘ahead’ even look like?” Where do you want to get to, and what are your options for getting there?

Evaluate your decisions against the goal, instead of the arbitrary divide of “30x500” vs “cool job alert.”

If you decide the job is just ‘cool’ but doesn’t really add to the direction you want to go, then I’d feel great telling you to stick to your guns and stay focused on the long game of 30x500 work.

But if the job adds to your long game in some meaningful way, charging ahead can mean something totally different! You can make decisions based on downsides you’re aware of. You can minimize those downsides through negotiation. And so on.

I hope this is encouraging, as it’s intended.

The next day, they replied again: “That is such a good response… I can’t really say more than that’s what I need to do, and thank you.”

Be wary of advice that promises a single universal answer, and instead, seek advice that helps you to ask better questions.

There's more where that came from

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