This is without a doubt the scariest post I’ve ever written.

I’ve tried to make this blog as useful as possible. With the exception of the odd frivolous entry, I’ve tried to give practical advice, stuff I’ve found helpful. What’s helped me that might help you. This means talking about things only after I’ve figured them out, after I’ve learned how to best get through them.

This is not one of those entries.

I’ve been reading I thought it was just me by Brene Brown, which is about shame.

After a decade of studying it, she defines shame as “the intensely painful feeling or experience of believing that we are flawed & therefore unworthy of acceptance & belonging.

The key bits here:

  1. It’s painful
  2. It’s a perceived external judgement (ie, about how we think other people view us)
  3. It’s isolating – makes us feel we’re alone
  4. It’s about something we feel we are (as opposed to something we’ve done)
  5. It’s about wanting acceptance

There are many other emotions that swirl around this, but what differentiates shame is that it’s about external judgement, combined with being about us (not our actions).

  • We feel guilt about things we do, but shame about who we are.
  • We feel embarrassment about events that are temporary, fleeting and eventually even funny.
  • Humiliation we don’t believe we deserve (eg it’s unfair), but shame we believe we do.

Other people can cause shame in us (criticizing who we are or what we’ve done – only if we interpret that as a personal flaw), but as always, we are our own worst enemy. Most shame is self-inflicted.

This is where the isolation comes in. Nobody likes to talk about shame. Nobody likes to admit it and that silence is, I suspect, the worst part of the problem.

Notice how people will only talk about rags-to-riches stories when they’re successful again (and thus distanced from it)? That nobody talks about riches-to-rags stories, unless they’re talking about someone else? That’s shame.

See the gradual realisation that Facebook is depressing us? (“Everyone else’s life is better than mine”) That’s shame.

We only want other people to see the best parts of our lives, and it’s a lie.

  • Every family is screwed up (in some way or other).
  • Everybody struggles – with addiction, depression, trauma, physical ailments, parenthood, self-comparison, work-life-balance, at least once in their life if not constantly.
  • Nobody is perfect – and by that I don’t mean “hair is sexily ruffled at 3am” I mean “is fucked in the head about something or other”

Because nobody talks about it, we think we’re alone, which only makes it worse.

So here’s where I’m at. Here’s my life, right now.

To give some perspective, I need to scroll back a few years. A while back, maybe half a decade ago I owned several properties (let’s just say, more than three). I flitted around the world whenever the whim took me. Stayed in $1200/night hotels. Didn’t think much of making $100k decisions based on a two minute phonecall (batting average on those? About 50%). I’ve dropped 50k in half an hour, and slept soundly that night. Made as much on a single deal with zero effort and thought “that’s nice.” Financially, at least, life was pretty sweet.

On a side note, I was pretty unhappy with who I was as a person (in a few ways), which is what lead to the spiritual journey I’ve been on since then – which this blog (mostly) chronicles.

About the time I started on this journey, my finances started taking a serious downswing. So, over the last few years, I’ve gone from the above situation to about a hundred grand in debt, with zero assets (nothing of any resaleable value).

I’ve been evicted twice in the space of two years. I’ve been taken to court. Threatened with debtors prison. Been forced to sell everything I owned to pay debts (& given the rest away because I couldn’t afford a moving truck). I owe significant money to a large number of people (friends & family alike).

I’ve had two girlfriends dump me because of it. I’ve watched my friends get tired of asking “are you making any money yet?” and slowly drift away. Several of them no longer talk to me (or reply with the barest of politenesses). This isn’t a criticism of them, they’ve been beyond patient – I can barely explain the situation to myself, I don’t expect them to understand.

I’m now 41 and living at home with my parents – the only place left that I could go. I’ve been here for a year (give or take), and (externally at least) still nothing has changed.

So where’s the happily-ever-after? There isn’t one – at least, not yet. And that’s exactly the point.

I’d been hoping I would eventually pop out the other end of things, so I could write a “Here’s what I’ve learned… now my life is all wonderful & shiny again” post. It hasn’t happened.

I haven’t written about this because it’s so shameful (and embarrassing, and humiliating).

If there’s something appealing about a 41 year old guy who is so incapable of looking after himself that he’s forced to bludge off his parents, I haven’t found it yet.

Is there any of the above I’d recommend? Well, getting rid of all your stuff; it’s challenging but ultimately freeing. Other than that, I wouldn’t wish it on my worst enemy. Stressful doesn’t begin to describe it.

Is it an awful situation? Yeah, kinda. Have the last few years been awful? Yeah, pretty much.

Oddly (or perhaps not), I’m the happiest, most peaceful and most loving I’ve ever been in my life. I can thank all the healing (as I’ve been describing here) for that. That part of the journey I wouldn’t give back for anything.

So what have I been doing all this time?

Well, a ton of healing (as you know), which has been super helpful. Without that, I probably would be dead. No, correction, I definitely would be dead.

I started a company, in late 2009. That was doing ok until early 2010 when two things happened. One, Twitter had loving-but-stern words with me about the way I was doing things (which involved a complete code rewrite) and two, Paypal shut down my account – temporarily – due to one of their apparently-common “security reviews”. Short version: something I did (or didn’t do) flagged some obscure setting in their software. I wasn’t actually doing anything wrong, it was just a temporary hiccup on their end.

Still, something about the confluence of these setbacks really kicked me… somewhere, and I still haven’t managed to even start charging people for the service again, let alone be able to pay bills or start making decent money again.

The bigger story is this: I’m an entrepreneur. My first job was when I started a company at 14, selling technical drawing paper to my schoolmates. I’ve always, always had side businesses on the go, no matter what I’ve been doing elsewhere.

However, there’s been a strong underlying pattern. I write amazing code, or build amazing things, but I rarely if ever make money.

When I invest (property, stocks, whatever), I generally make out like a bandit, but businesses I’ve started (and there’s been a lot), no.

This is a pattern I want to break.

I don’t want to spend the rest of my life starting businesses, working hard, and getting nowhere. That’s stupid. It’s neither loving nor helpful to myself.

Of course, whatever is going on is just something emotional. I’ve created it, and I very definitely have the tools to break it.

I just haven’t been able to do so yet.

If I don’t, eg if I follow most of my friends’ well-meaning but misguided advice to “go get a job”, well, this issue will just continue to re-manifest for the rest of my life. I’ll keep recreating it in new and exciting ways. This is exactly what I’ve already seen happen several times, so it’s time for it to stop.

Making the time to sort this issue, even if it means abject poverty for a couple of years, is worth it for the pay-off over the next hundred.

Logically, there’s absolutely no reason why I shouldn’t be rolling in cash. I’m male, white, well educated, have a broad experience in a bunch of high value fields, hard working, skilled, motivated. All these things work in my favour. I fully realise how blessed I’ve been to be born into the situation I was. Whatever’s going on here has nothing to do with the obvious.

The thing is – I can tell myself all this. How counter-intuitive it is, how unlikely, and how necessary to sort it out.

It doesn’t make the situation any less shameful.

It’s not an accident I’ve been single for almost three years. How do you ask a girl out on a date if buying a coffee is something that will most likely take a month to budget for? What about a second date, wait another month? Awkward.

Plus, of course, shame is always accompanied by powerful feelings of “Not good enough.”

Statistically, most people work for others (as employees), whereas I’ve had a very non-standard career. This makes it difficult for most people I know to relate, let alone understand (isolating).

In Silicon Valley maybe, running a startup would be understood. Even there though, when a startup gets funding (from a VC, typically), that’s considered “success.” Until that point (or an IPO) they’re not generally considered successful. Even bootstrapped (ie, no external funding) startups are considered a bit weird, interesting, but not-as-successful.

Where my parents live is over an hour by bus from the nearest city. There are wild chickens that live closer to it than I do. It’s where I grew up and while it has its charms, this is the most provincial I’ve lived since I left home, 24 years ago. This is no accident. I thrive on the bustle of cities, and even telling people where I’m currently living is mildly embarrassing.

All these things – they’re all my perception of how other people will view me.

None of these things I’ve wanted to talk about with anyone (except my family, whom I love dearly). Even writing this is scaring the shit out of me.

To be clear. I’m not posting this because I’m looking for sympathy. Or solutions. Or even empathy (although generally that is the ideal response to someone talking about something shameful). I’m posting it because we all have things we feel shame about, and not talking is worse than the discomfort of admitting them.

Yes, I am aware that once this is on the internet, it will exist forever, and be indelibly connected to my name.

Again, shame. And again, this is exactly why this should be posted.