Some things are supposed to be hard

the view from my old place - Fort Greene, Brooklyn

"I just want you to tell me what to do." 

I said this to Claude the other day. Outsourcing my stress, my agency, my decision-making process to an LLM — literally asking it which path to choose, as if I hadn't had much more difficult things to decide in my life:

  • whether or not to leave Brooklyn for CA

  • whether or not to stay married

  • whether or not I should leave tech and start my own business

  • whether or not I should go back to school

  • too many decisions to even count related to my kids well being, education, and daily lives 

A client also said this to me a couple of weeks ago, and it's certainly not the 1st time I've heard this from one. It's expected in coaching, and expected in our complex lives.


It comes up without fail during our pivotal moments - big transitions, and decision points in our lives - the kind where no answer feels like the right one, and you can't quite find solid ground. It comes up at work when you and your team cannot get on the same page enough to charge forward.

It's a natural reaction to uncertainty, and even more so during the era we're living through--where each day brings something new, unsettling, and destabilizing - and we're being convinced there's a faster, smarter, more efficient way to think, create, and decide…to be.

We want to skip the anxiety. Rush to the good outcome. Push through whatever we're feeling, and get to the other side. 

Sometimes we avoid the friction altogether — we procrastinate, we put it off, we avoid. Or we go the other direction: seeking quick fixes and hits of dopamine, or numbing it out.

We seek solace in whoever, or whatever, promises to make it simple, to have the answer, or to take the onus and accountability off our plate--someone who “knows”, and can predict. Someone who can lighten the load. An app, a person, an AI coach, a therapy bot, or an actual therapist or advisor.

I love efficiency. I love what AI is doing to democratize access to information, tools, capability. But there are some things that inherently require friction, and make our lives, our relationships, and our careers much more rich.

Here are some kinds of friction to keep for your growth, well-being, and a career and life well lived:

  • Existential questions about your value and purpose - or what you are doing with your life, and your career

  • A direct report you know is going to get emotional, so you avoid the converation, or put it off, or prepare a hard script

  • Making a major career decision—a pivot, whether to stay or go

  • The kind that comes from a mentor/therapist/coach/advisor or friend who pushes back and challenges you, instead of cheerleads

  • The tension between functions at work when it comes to decision making— GTM and ops. Ops and finance, engineering and product, etc.

  • Suddenly feeling out of place in your environments, and social circles

  • Friend dynamics that feel “off”, or a series of conversations landed on you badly

  • Disconnection from yourself, or from your partner

The friction in these circumstances often surface something important — a blind spot, a risk, a cultural signal, or a potential change you need to pay attention to (and maybe even do something about).

A reminder these hard parts aren't an obstacle. Get support to tackling them, yes - but don't completely outsource it -- this is where the beauty, and the growth actually happens.

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On The Career I Almost Left