I don't own much stuff. My entire closet fits into a medium duffle bag. Spending money on things isn't something I enjoy too much.

You can ask my family how annoying it is to buy me gifts. I squirm like a baby in a high chair getting force fed goop.

One thing I'm not shy to spend money on is coaching.

Over the past decade, I’ve spent close to $30k out of pocket on coaching. Some highlights:

• Computer science: the first experimental cohort of Bradfield with Oz, Myles, Salar, Alex, and the rest of the gang.

• Engineering leadership: an early iteration of Edmond Lau and Jean Hsu’s coaching program for leaders in the tech world.

• Art education: Kevin Murphy’s incredible painting program.

• Design: Erik Kennedy’s online design curriculum and community.

• Writing: David Perell’s writing workshop. Venkatesh Rao’s “thinking” workshop.

• Health: a monthly subscription to Future Fit and my trainer Manny. Meditation instruction from the Aro community. Nutrition coaching from PD Mangan.

Was this $30k worth the investment? I shall briefly examine using the following lenses:

1. Financial

2. Mindset

3. Community

1/3 Financial ROI

I paid $15k for 3 months of study with Oz & Myles at Bradfield. I paid $5k to study with Edmond & Jean in their 6-week leadership program. At my next gig as a programmer, my salary increased $75k in 12 months.

I punched way above my weight class (junior engineer with no formal computer science degree). I learned the fundamentals of computing very deeply, and so reasoning about software challenges became a matter of finding the right question to ask. I learned how to lead (not just manage) a software team and how to communicate effectively with other teams, despite being a total newb.

The arithmetic on these two works out to $20k down for a $75k “measured” return. The ROI: 3.75x in 12 months.

But this type of simplistic financial analysis bores me to tears. It’s a great starting point, but it’s not why I chose to invest in coaching.

2/3 Mindset ROI

When college students study abroad, they often come back transformed. It goes beyond a mere change in hairstyle and music preferences. Immersed in a foreign environment, they expand their concept of what is possible to become.

A similar process takes place when freshmen move into the dorms, or cadets go off to training camp, or a homebody moves to a new city.

Opportunities for these types of major shifts in mindset become less available as one gets older and progresses in career or vocation or responsibility load.

Sure, in an ideal world, we can transform ourselves simply by sitting on a cushion, going for a walk, and doing the work. But anyone who has been stuck in a rut knows it really helps to get help from someone credible who’ll hold you accountable.

Coaching creates fertile ground for mindset transformations to occur. There is a master giving you feedback along the way. If you start dogging it, they’ll notice and get you back on track. This type of direct transmission allows lessons to hit a register that reading a book may not be able to do.

Some examples:

I used to binge my work sessions until I started studying art with Kevin Murphy. Now I more often work in smaller, focused sessions.

I never used to go for long morning walks before I started training with Manny and PD Mangan. Now I try to get 8-10k steps in every day.

All of these small, subtle adjustments in mindset compound over a longer period of time. It’s hard to tell the exact ROI of mindset change, since many of these coaching sessions are still in progress and I’m still struggling to internalize many of their lessons.

So ask me in a couple years. If I’m doing something vastly more interesting than what I’m doing now, then the ROI is probably pretty strong.

3/3 Community ROI

From my experience, the financial and mindset ROI of coaching far exceeds that of having gone to college. I’m just one guy, though, and I perhaps got very lucky with timing.

College taught me how to slack efficiently, and it left me totally unprepared to fend for myself in the real world.

Coaching, meanwhile, taught me that everything is a craft that can be improved and worked upon. More compellingly, each coach imparted on me something of practical value — accomplishment. I didn’t have a credential to wave around, I had an actual body of work.

For these reasons, I strongly believe that unless a field is gatekeeped by credentialism (law, medicine, etc), there are few reasons to go back to traditional academics.

There’s only one reason why anyone should return to school methinks: Community.

I got lucky because the fields I wish to study have master-level coaches building niche communities around their craft and instruction. Thanks to many (but not all) of my coaches, I have met other folks grinding away on similar problems and questions. This additional source of inspiration keeps me motivated and unstuck.

But I am aware that some fields do not (yet) have easily discoverable coaches and communities outside of traditional higher education. Don’t hold your breath, though — that too will change in the next decade.

Hope you enjoyed this one. I’m slowly pulling together a big list of coaches and programs like the ones listed above. If you’ve got some you’d recommend, let me know!

I’m kickstarting my Twitter in the next few weeks. Give the homie a follow if you're active there.

Until next time,

Ammar