I'm touched by your vulnerability and openness. It reminds me of a client who had built a billion dollar company and wanted my help building his next one. My immediate sense was that that was not really why we were talking or why he was here. We kept going and eventually I challenged him asking whether he had really built a billion dollar fortress to never need to be vulnerable. He broke down and we went deep, uncovering some of the deepest trauma I'd seen someone go through when they were 4 years old. From there, everything shifted and things took a very different direction. It's those kinds of insights, when as you say "as my healing journey has progressed, any ambitions I held to achieve business success on par with the Airbnb founders has faded, and been eclipsed by the realisation in order to anything really well – from running businesses and leading social/political movements, to simply having successful friendships/relationships, a healthy family life and a physiologically healthy body – a healthy emotional foundation is of prime importance.", once we really get in touch with our inner world, things shift dramatically and what has meaning to us changes. That doesn't mean that we don't want to to continue having a meaningful contribution to the world, but the sense of ego-striving that is often just a mask for our wounds can gently fall away and allow us to walk through life a little more freely.

My learning has been whether you get to the billion dollar level or not, the untouched wounding eventually comes through and takes its toll if it stays unaddressed. It's stories like yours and the one I've described that make coaching the most meaningful thing I've done in my life to date.

Cheers for that.

> the untouched wounding eventually comes through and takes its toll if it stays unaddressed

This nails it, and I think a lot about this in the context of the very public cases of "unicorn" CEO falls-from-grace in recent years.

> That doesn't mean that we don't want to to continue having a meaningful contribution to the world, but the sense of ego-striving that is often just a mask for our wounds can gently fall away and allow us to walk through life a little more freely.

Very nicely put, many thanks.

Great book on this topic is I Don't want to talk about it by Terrance Real

Isn't this just essentially just a reflection of maslow’s hierarchy of needs? I mean, everybody has their demons, and the founder of the billion dollar company has the time and resources to face those demons by receiving top quality professional assistance, leading him/her closer to some kind of self-actualization. Whereas a large majority of the population (even in developed nations) are still struggling on much lower levels of the hierarchy, such as fulfilling their "safety needs" (e.g. employment, health, etc).

I would therefore argue that the "untouched wounding" remains buried for most people because they are never in a position to address it, and the "ego-striving" remains essential part of their survival toolkit. There is simply no "salvation" in this regard for most people and it's quite sad.

No. Emotional healing became my top priority when I was effectively broke and homeless. I mean, I was crashing at my parents and friends’ places, but it was a profoundly miserable (and low-Maslow) state of existence.

Founders of break-out successful companies don’t just voluntarily embark on emotional healing practices once they reach the pinnacle of business success. They generally do that when they suffer a humiliating fall from grace. E.g., Early-career Steve Jobs and Jack Dorsey.

Also, Maslow’s model isn’t really broadly accepted in mainstream psychology, certainly not in any linear sense.

There are a lot of rich people out there who have all of their Maslovian needs met but who are absolutely miserable. What happens is that they never really figured out what they wanted out of life, they just assumed that having money would allow them to get it, and they'd figure it out later. But then they get money, realize that they are still miserable (because they still don't really know what they want) and then sink into deep existential despair because if you have a billion dollars and you're still unhappy, now what the fuck do you do?

Ron's second law: the hardest part of getting what you want is figuring out what it is.

This is a prime example of survivor bias. Most homeless people don’t make it back to the top.

I tried to be clear that I wasn’t “homeless” in the sense of living on the street.

I just couldn’t make rent (ironically I had to Airbnb out my room) or easily afford food/bills, so needed to sleep at parents’/friends’ houses for a while as I worked to get back on my feet.

Plenty of people go through this, due to a business/career/relationship breakdown, and recover to a good life, and it’s very common for people to start focusing on their emotional/spiritual wellbeing when they hit rock bottom (e.g., join 12-step programs, counseling etc).

People who are chronically homeless are in a different category, but it’s widely accepted that chronic homelessness is usually linked to mental illness and/or addiction (which is a form/symptom of mental illness after all).

I’ve spent a lot of time thinking about how outcomes for chronically homeless people could be improved if they had access to the kinds of support and healing techniques I’ve used. Given the opportunity, I’d be very willing to support research into this in the future.

Invoking concepts like “survivorship bias” is unhelpful in a discussion like this; my story is obviously anecdotal, not an academic paper or claim of scientific evidence. But that aside, “survivorship bias” in this context would require the existence of a whole lot of people who attempted the same approach to emotional healing that I did but failed to improve their lives, and there’s no evidence for this.

I couldn’t disagree more. I think free healthcare, aides for rents, food, etc. when you can’t afford it should be a human right. Some people manage more than others, and we just blame this on mental illness.

> Some people manage more than others, and we just blame this on mental illness

I agree, but I don't accept that this has to be immutable, and it would be a very bleak world/future if it did.

Rather than a world in which a class of people just has to accept a disempowered existence with basic services and resources provided, I hope for a world where effectively everyone can have agency over their own life, and aspire to good health, good relationships, and a reasonable level of material wealth.

That hope is part of what keeps me determined to explore the possibilities in this field; to see what kinds of improvements I can attain in my own life, then think about how these approaches could benefit others, including those who are currently written off as "mentally ill" (which I have been at certain times in my life).

I think I understand what you mean with that and agree with it in principle. However you should keep in mind that you are a person with a "business mindset". There is plenty of people out there who may well have something valuable to contribute to this world, but have no chance of getting an economic return out of that. This can be due to a lack of economic mindset/understanding/education or also just due to the type of value one is able to provide not fitting any monetization model. I believe that a modern society can and should afford to relieve their members from existential fear related to biological needs. That is not about taking away aspiration and agency.

The combination "something valuable to contribute to this world" and "have no chance of getting an economic return out of that" sounds like a market failure, and something that could/should be fixed, both for the benefit of the individual and for society.

There are indigenous Australians in remote communities, who grew up and remain living in cultures that have little familiarity with modern commerce, but who produce artworks that sell for thousands of dollars on international markets. The proceeds are invested back into those communities for their future benefit. This happens because systems have been established to make it happen.

So I'm not convinced that there is an immutable state in which a certain class of people, while providing valuable contributions to society, cannot reap any economic benefit or improve their own lot in life.

Can you describe an example of this situation that you've observed?

... in other words: based on personal observation, I believe that the correlation of personal wealth and value contributed to society is not strong enough (which doesn't mean there's none) to justify making one's existence dependent on it - in a sophisticated society which could easily afford otherwise.

To add to this, when your ego mind drivers lead you to success giving you potentially unlimited resources - money and time, it is easier to maintain coping mechanisms of distraction - unless there's some traumatic or stressful enough event that "cracks" someone, causing an impetus and necessity to explore change.

Western philosophy starting from Ancient Greeks has offered a variety of coherent life philosophies that both help with untouched wounding and ego-striving. The books provide cheap and accessible salvation which is just not in demand by most people and it is quite sad.

Wow. Thanks for that.

When Airbnb popped up on my screen I was in Siberia having my website rewritten from scratch after 8 years of spaghetti code.

It was the same thing and Airbnb which was just designed better (in 2008).

When a couple of years later I finally realized they destroyed my business it took me some time to admit I didn't really miss a chance: I had none to begin with.

I just don't have what it takes to grow a business to those levels.

In my case it's probably not an emotional issue, but it has still a lot to do with personality.

I guess my takeaway is: not everyone can be a CEO of a unicorn and this is fine.

> I just don't have what it takes

Try not to put yourself down like that; it might just be that you were already grounded and emotionally centred enough that you didn't need to chase the riches and fame :)

I guess you are right. I think my biggest block to success was that I was just to happy! :) The very reason I had started that business in 2001 was because I wanted to travel full time.

I managed to do that and I was already in a "too good to be true" state of mind.

The happiness and fulfillment I got from those years are now my own "essential oils" for the occasional hard times. When something goes wrong I just have to go back, smell a drop of that, and I'm back on my feet in no time.

I wasn't just looking to grow the business, it was a mean to an end.

Thanks for sharing this, if you don’t mind to elaborate, what aspects of personality do you think have more weight? Have you consider partnering with someone who complements those aspects?

My anecdotal opinion - pure tech people don't usually make good founders because they are too realistic and grounded.

A company needs a visionary, someone who is at times even blinded by their optimism and vision. You pair that visionary with a strong grounded realist, and they balance each other out. There are times when both are needed - to either take a leap of faith (risk) or mitigate/avoid risks.

But this dynamic will also only work if these founders have good communication and respect towards each other, otherwise friction can turn into bitterness and resentment.

I think we should not force ourselves to become something we are not.

If you've got the Unicorn CEO personality, go for it as it would be a pity to be stopped by fear.

If you don't have it, why chase the social norm of the day? You won't make it and you'll be miserable.

Again, not everyone has to be a CEO.

You can be great at something else but you need to be blind to the social requirements of your age.

What is cool today wasn't cool 20 years ago and won't be cool in 20 years time, anyway, understand this and you are free.

Maybe we will look back at the "be big or go home" days as a skewed approach to business fuelled by VCs need for high returns.

And yes, today I look for partners who can complete me, as I have millions ideas but I only enjoy the first part, where you go from 0 to 10, growth 10 to 1000 is boring for me and I'm not good at it.

BTW, if anyone is good at it, I have great ideas in the Vacation Rentals (Airbnb) market, my contacts are in the profile.

I agree. In my case it's not ethics as I enjoy working hard, but as it gets less interesting and goes in growth phase I'm already chasing the next idea.

I was just kidding btw. The AirBnB founders just got lucky.

They knew the right people to get into Y Combinator. Their original idea for air mattress rental is a really dumb idea. It's a miracle that they got accepted into YC.

It is difficult deciding if this is inspiring or discouraging. The way you describe the Airbnb founders it feels like they had some intrinsic ability or talent. I think I have always viewed failure as not working hard enough, or smart enough, almost getting there but just not quite getting it right. Reminders that you may be failing because you might just not have ‘it’, and that no amount of work will get you there are kinda brutal.

I always think back to being 8 years old and running with my friends. Some kids were just faster, others were slower. No one was training or working at it, no one was reading up on techniques at night. Some kids were just better. Are most of us just the kids in the middle trying to be the fast ones? Is self-acceptance, tempering of expectations and emotional growth a road to happiness or the silver medal of people who were just not good enough?

I’m confident there’s a way it can become encouraging.

Learning the skills (programming, design) to build an early stage web/mobile product is not hard; many many people already have done or could do that.

Equally, plenty of people can easily identify political or social problems that just need a confident and capable leader to drive reform.

The temperament/emotional side seems more innate and immutable, but only because broadly accessible ways of transforming one’s temperament are not widely known or deeply researched.

This is one of the main reasons I’ve gone so deep on the topic; beyond just the self-motivation of improving my own life, it seems like it could be quite significant if many more people in the world were able to overcome their inner obstacles and achieve better outcomes in whatever they were seeking to do.

Temperament definitely changes with age at least, the timescale for personality shifts is just so long that it’s difficult to manufacture or steer them.

> Are most of us just the kids in the middle trying to be the fast ones? Is self-acceptance, tempering of expectations and emotional growth a road to happiness or the silver medal of people who were just not good enough?

I used to race bicycles competitively, and our coach grilled into our heads: "It's you vs. the track. The other racers are just obstacles in your way. You are not racing them, you are racing yourself." I was a mid pack racer, but that mentality, of focusing on personal growth was huge.

You define success for yourself. And by your measure, others may be more successful on your own measure, but they are not you.

I'll also add the trite: "hard work will be talent if talent doesn't work hard." My brother was a natural racer, but he hated to practice and got beat by riders who were better conditioned all the time.

He never had to beat them, he just had to beat himself.

Wasn’t that kind of op’s argument? You can focus on beating yourself all you want, if yourself isn’t the best, then you will never win the Tour de France.

If you don’t have the potential to win The Tour, then should you even be trying to? Sounds like a lot of effort, might wanna invest it somewhere else or redefine your cycling goals.

I run marathons and I don’t beat myself up about winning because I don’t have the potential to be a world class marathoner. Even if I trained twice as hard as Kipchoge. I just don’t have it.

Same with boxing. I train 4x/week because I enjoy the exercise and mental relaxation. Punching people in the face is fun. But I don’t compete because I don’t have the talent to make the pain of competing worth it.

But when it comes to writing software and running a business, you bet your ass I’m giving it all I got and want to “beat” (hard to define) everyone else. Because there I do have the potential.

What kind of bike racing was that? Because road racing is quite the opposite, the other competitors are everything while the properties of the course are just a minor influence on the all-defining question of which wheel to suck when. But those coach words are still wise and apply even there, if your goal is not to maximise winning but to maximise motivation and happiness (which would actually help winning long term, but the ratio between winners and losers is so bad in that game that you should focus on happiness nonetheless)

I agree but it’s also worth noting that you should also be able to step back and consider how much of your self worth you want to define by how fast you ride a bike. There’s good reasons to set goals and “beat yourself” but also good reasons to not worry about it too much and “accept yourself“.

I think life is incredibly unfair, more so than people care to admit. Personality, disposition, early-childhood parenting, where you grow up, physical appearance, intelligence, family, surrounding, even country you're born all are determined outside your control. Yet these factors are what more or less determine how successful you are going to be.

The way I look at it, if you're posting on HN, you've mostly likely been dealt very favorable hands in grand scheme of things. So I try to be thankful for what I have.

For all each success stories like AirBnB, there are hundreds of not-so-successful ones with equally competent and gifted team. Luck plays a huge part.

Interesting approach and I feel the burn of this quite often. Peers of mine have much greater hands dealt and I've worked quite hard to get where I'm at... I get bitter sometimes because theirs nothing I could have done to set up greater nets for myself or anything like that.

The disparity of equality and seeing the top after coming from the bottom makes you realize just how unequal things are and how it might just never change and get worse.

I had a psychotic break and almost torched my career and I had a similar epiphany that emotional stability trumps everything. My only critique is if you frame emotional stability as a foundation to achieve all these other ambitions then to some extent you’ve circled back right to where you started. The emotional stability is it’s own reward and worth infinitely more than a successful business.

By the way, since someone has already asked (and I generally get requests for more info when I write about this stuff here) people are welcome to contact me if they want to know more about techniques I’ve used for emotional healing.

I’m working on some written material to share my learnings with others who may benefit from it, so if you get in touch I can share it when it’s ready.

Email address in profile.

Thanks for sharing your story.

My own story has some similarities to yours -- I joined an elite startup accelerator straight out of university, thought I had a bunch of pretty damned good business ideas to work on (and looking back, I did -- I had a pretty good understanding of business strategy, engineering, product design, etc) -- but then ended up bouncing between jobs and quickly-aborted startup attempts, before crashing pretty hard around age 26-27. Meanwhile plenty of my peers steadily moved forwards while a few others shot off into the stratosphere.

I actually knew Leo Widrich, author of the article, back in university! Two guys had set up the "Internet Entreprneur Society" at our university in the British midlands, I was helping them run it as they were about to graduate. Leo was an Austrian business student with lots of passion and just starting to learn about tech startups. He ended up working with one of the two guys I mentioned (Joel Gascgoine) on some tweet scheduling app which is now apparently worth about $80m :) Small world!

As for myself, after several setbacks in my late 20s, I realised I had a whole bunch of psychological/emotional issues stemming from an unstable childhood. What's surprising is that with time and effort all these problems were, in fact, fixable... and through lots of reading and self-work I've managed to fix 80-90% of these issues. Like you, my desire to build a startup business empire has diminished greatly, and, nowadays, after learning all the things I've learned, I've rethought my career plans, and figured out a new direction to go down which ties together the various things I'm interested in, and which I'm very confident I can succeed at. (I'd rather not go into details in a public forum, but's it essentially a path that combines intellectual and technological projects).

(For those in a similar situation, the best books I read were: "Adult Children of Emotionally Immature Parents", "Running on Empty: Overcoming your Childhood Emotional Neglect", "Complex PTSD: From Surviving to Thriving" and "Psychology of Self-esteem". I also recommend the post "What is a central purpose in life?" (plus comments) [1] for a discussion of how to integrate one's career values).

[1] http://aristotleadventure.blogspot.com/2008/05/what-is-centr...

Fantastic, thanks for sharing.

“when you really have it together yourself, you have plenty of positive energy to share with others.”

That’s a really important point. I tend to think about is an emotional gas tank. When it’s full, it’s much easier to be generous and help others. On the other hand, if your gas tank is empty, you are busy enough to keep yourself going and have no capacity for helping others or even for compassion.

I always wonder if some place like YC could use a resident therapist/psychologist. Someone who meets with founders as needed or on a weekly basis. Might be helpful.. After watching the Showtime show "Billions", the idea seems like a pretty interesting innovation.

They had Amy who was a trained psychotherapist during both 2015 and 2017 when I went through. Anyone could schedule time to talk to her at anytime but it was generally used for resolving founder conflicts. She went off to be an executive coach but I am sure they still have someone like that.

It’s a sweet thought but there would be far too many conflicts of interest for a single therapist to operate ethically.

It didn't even operate particularly ethically in the TV show either... still, seems to have been effective

Maybe.. there's probably a way to make it work though.

2 minutes to twelve, but definitely a candidate for best comment of the year.

Tom, could you please share how you've worked on your emotional wholeness? This is an issue I recognize in myself, but do not know how to begin to heal.

>And as my healing journey has progressed, any ambitions I held to achieve business success on par with the Airbnb founders has faded, and been eclipsed by the realisation in order to do _anything_ well – from running businesses and leading social/political movements, to simply having successful friendships/relationships, a healthy family life and a physiologically healthy body – a healthy emotional foundation is of prime importance.

I feel also one has to realize that he can't have it all in life. I think its almost impossible and out of our nature to be able to achieve greatness in all fields. You might be the most successful CEO in the world and having the most money in the world but that doesn't mean that you are going to have and lead a successful family life as well.

Same way you can be successful at having a nice family and a loving partner etc but that requires time, time which you'll not be able to invest the time that being a CEO requires.

Thats my personal take from life so far - you have to decide what you want to be.

This has to be one of the best comments I've read on HN.

I've failed many times in my life on different adventures and it has always been because I couldn't see what was really going on due to frustration, emotional traumas, etc. Of course hindsight is 20/20 and I can see that a lot more clearly now that I turned 40.

Thanks for sharing that personal insight.

My career is far from the place I want it to be and I've emotionally dealt with the setbacks by changing how I interpret failure.

I used to think of failure as lead bricks I'd collect and forever lug around whenever I didn't meet a goal. An infinite burden with no purpose.

Now I think of failure as a heavy work out. Rather than bearing a burden of failure, I fill the experience rips/tears with knowledge protein. It's a semi-silly analogy, but it's really helped me. Knowledge + experience = wisdom.

PS. Adioso is great.

What really resonates when reading your excellent post here is that Marcus Aurelius was really on to something with this brand of stoicism. Reading Meditations is difficult because of the style and just translating from 2000 year old language rather different from English but it seems very relevant to the life of a founder, any leader, or really anyone.

Thanks for sharing Tom. I enjoyed your recent LI post about some of the recent successes you’ve helped create in multiple businesses - it really seemed (with all the social media caveats) that you’ve been focused and continue to create enormous value around you.

Oh thanks for that.

Funny for you to observe that I've seemed “focused”.

I've often though that to an outsider who isn't right beside me on this journey, I'd seem incredibly unfocused; since leaving my startup I've worked on almost 10 different projects or contracts.

But what I've actually been doing, mostly very privately, is undertaking a highly focused project/experiment in deeply healing my mind and body, whilst doing what I need to do to make a living along the way, and doing what I can to keep the ball moving forward towards some fuzzy long-term career outcome and/or life purpose.

And yep, it does all seem to be yielding some solid results, but if it looks like I've been focused, well I think that's a happy accident :)

Any chance you can point to the starting point for your project/experiment? Such as did you find a book that helped you to start asking a set of questions about yourself. If so, what questions seem to being making the biggest impact?

Also, just wanted to say thank you for posting about this. I realize this really private stuff and I'm trying to find my own process for something similar to this.

I guess, as a consultant, for me working on multiple projects or with different businesses is just part of life.

To actually be shipping outcomes: that takes focus.

And I’m glad to hear the ‘source’ project is also progressing strongly.

Thank you for this. It made a whole lot of difference today.

Thank you for sharing so openly! My career and business life has been at best mediocre by most common measures. The inner journey though has been immensely rich.

Very interesting that your batch recognized that the emotional strength and stability was the important part, rather than the idea.

I doubt that the whole batch had some sort of collective epiphany that made them consider "emotional stability" a key metric. The way I read the story they voted impressed by variety of seemingly unrelated things that all made them stand out in very pragmatic ways that tomhoward only much later identified as sharing a root cause in emotional stability.