How Do You Leave Money On The Table?

A few people sent me Ali Abdaal’s most recent video and I thought it was one of the most interesting I’ve ever seen from someone in his position, with endless opportunities at his fingertips.

It’s about his internal struggle between competing interests: money or life enjoyment.

Spoiler: he’s actively embracing an approach with his business and life that chooses to leave money on the table.

I found it fascinating to watch. At many moments you see him twitch and scratch his head as if his rational brain inside him is trying to stop him from what he is doing.

I’ve consciously chosen the “leave money on the table option” over and over again and I’ve tried to do this from the beginning. My biggest reason was that I wanted to see what happened. True fuck around and find out energy.

Most of the time? It felt silly. Like I was wasting my talent, lighting the ten years of intense consulting and business school training on fire. But also over the last 6-7 years, it’s sort of worked. My days are nice. I’ve spent 98% of my days on my terms and I’ve felt better about the person I’ve become.

But if I laid out my decision to people in my shoes now it would be an active choice to give up $1M of incremental income that I easily would have earned if I had stayed on my former path. While I think I still could have turned it down, I realize its damn hard for most people.

I am lucky. I found work I like doing, writing, and want to keep doing for another 10+ years. It always seems like there are things I can improve and my curiosity never seems to fade. On top of that, I’ve slowly built solid relationships by taking advantage of not having to ask people for help.

Ali talks about being uncomfortable asking podcasters to help him promote his book even though almost everyone would likely be happy to do it. I get this. I sense the discomfort comes from the acknowledgment that we are turning a potentially meaningful relationship with another human into something that starts as a transaction. I sense this is what’s been behind my interest in leaning against the obvious financial opportunities. I don’t feel like I’m wired for a business battle. I genuinely want to hang out with people that inspire me.

I was at an event this week with some VERY successful creators and there was a part where we had to ask for help. I asked people for help getting on some BIG podcasts and while doing it my voice cracked. It’s still weird. I know my book is pretty good now and I’m a lot more confident about saying that it’s a banger but I still have some latent insecurity, work scripts, and a genuine desire not to mix work with connection that holds me back.

Over the years I’ve left money on the table in many ways:

  • Not doubling down on my StrategyU business which has much more potential because it doesn’t feel like I can do it for 20 years
  • Never tried to make money from writing for five years and even with the book didn’t see it as a money-making thing (which has made the money a delightful surprise). I tried getting into a proper publication once and then didn’t again because I didn’t feel good
  • I didn’t do a book launch or tour because I just don’t feel good thinking about it
  • I didn’t sell my book to Penguin because the conversations didn’t feel good

In the video, Ali similarly says, “I don’t want to do stuff that feels bad.” He continues, “I don’t want to do things that I don’t want to do. That probably means I’ll have a smaller business than other people.”

This must be hard for him to say.

As many of you know, I’ve gotten to know Ali over the past few years. He’s generously shared his audience with me despite me never asking. Maybe he senses that I don’t feel good asking either?

The interesting thing is that you can leave money on the table and there is an interesting opportunity to share with people about what it feels like to do that.

That’s a lot of what you all are interested in and as I’ve found out there’s been a hidden audience of people that want to hear about unconventional approaches to life.

Right now, there’s an open portal to experiment with your life and pair it with creativity. Sharing videos like Ali, or writing like me. EVERYONE knows how to google the ultimate best practices and I think this is great for some people but drives a bunch of other people crazy. We are long on tactics but short on sharing ideas around the inner game of how to carve a path that is true to your own nature. This is a great thing. We need more “experiments in living” as John Stuart Mill once wrote.

In a podcast I did with Tim Malnick, he detailed two paths: the money path and the life path. The money path is the belief that “one day when I sort this out I’ll get to do what I want.” Suffer now for a future payoff. The alternative is something he calls the “life path.” This is the idea that you can “do what you love and the more you follow it you will have your needs met with and without money.”

And the key thing here is the second path: your needs met with and without money.

And this is what I’ve experienced. I’ve left tons of money on the table but I’ve been compensated richly with time with my wife, with my family, with my daughter, space to think and grow as a person, new friends who are willing to spend time with me, and an overall psychological richness that I would never give up.

Ali shared an email he received from April Perry that’s amazing and puts it far better than me:

Hey Ali,

People always talk about leaving money not the table like it’s a terrible thing. Why don’t you sell another digital product? Why don’t you do a mastermind? What don’t you sell physical products?

But no one ever speaks of the mental and emotional costs associated with managing all of that.

I think we need to shift our perspectives. Why are you leaving peace of mind on the table? Why are you leaving family time on the table? How about mental health and being enough with what you already have and do? How’s your connection with god? What’s the quality of your marriage? Can you just sit and just sit be? Can you laugh and sing and truly relax with loved ones? Can you look at your relationships and nature and all that God has given you and sit in awe for a moment?

It doesn’t have to be either/or but all that if I have my family’s financial needs covered, the first thing I’ll leave on the table is money.

I’ve embraced a lot of this because I read many books about people’s regrets at the end of their lives or regrets after “making it” and decided to take them seriously. I thought, “What if I skip the aiming at success thing?” and tried to aim directly at what those people said mattered.

About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.