As previously promised – threatened? – here is the sordid story behind me not going to college. There is a lesson here.

When I was 19 and pregnant with ill-planned child number 2, I was working in a check cashing center. I had a small two bedroom apartment. I could afford the apartment or I could afford furniture, but not both. Michael – child number 1 – then age 2, slept on two crib mattresses duct-taped together. I slept on a duvet.

One day when I was at work, the father of child number 2 decided he did not want to be the father of child number 2 and left.

That night my brother came over. (Child number 2’s father had left some beer in the fridge and hell if my broke grad student brother was going to leave free beer to rot in his pregnant sister’s fridge.)

He asked me what my plans were now.

I don’t remember what my reply was, but we are safe to assume it included some dirty words.

“Like, are you going to go to university?”

I was absolutely shocked by his question. Was he completely insane?

“I can’t go to university! I’ll be TWENTY-THREE by the time I’m done!”

To my mind, finishing university at 23 was about the same as paying for your tuition with your pension money. Seriously. 23? How over the hill was THAT? How could I possibly get a decent job if I didn’t graduate until 23? Jesus. That’s an entire YEAR older than anyone else would be. Employers would scoff. I would be a laughing stock.

“You’re going to be 23 anyway. Did you have anything else planned?”

Now, with some hindsight, it’s fun to look back at a 19-year-old thinking 23 was a hundred years away, so far away that it wasn’t worth embarking on anything new.

It’s fun to look and say, “Oh, the follies of youth.”

It’s fun to say, “She didn’t even know she had so much time ahead of her.”

But at the time, it felt like the most pointless thing in the world. I was fucked, and anyone who said I wasn’t was just trying to make me feel better. It’s like the little boy diving face first into shoveling manure saying, “With this much horse crap, there’s bound to be a pony around here somewhere!”

I said as much to my brother and – God love him – he paid about as much attention to me then as he does now. (That’s a nice way of saying he ignored everything that came out of my mouth with the exception of the parts he could use to make his argument stronger.)

At some point in the conversation Michael mercifully woke up and gave me a chance to leave my brother to his ill-gotten beer.

When I came back he said something that, honest to God and I’d never say this to his face, changed my life.

“This doesn’t have to be your life, babe.”

I wrote that on a piece of paper and put it above my duvet.

I did not go on to university. A few years later I borrowed $12,000 from the government to try graphic design at community college and dropped out after three weeks. I worked in temp jobs and I worked in bars and I considered stripping but I didn’t have the boobs for it. (See: two children, above.)

When I was 26, I started IttyBiz. That worked out well, I guess. And I can credit starting it with the small part in the very far recesses of my brain that always remembered, even a tiny bit, that this didn’t have to be my life.

How to end your life.

I recently read a book called This Is How. It’s a book of essays on how to do the really, really, really hard stuff. It’s editorial, not instructional, and it’s basically designed to pull back the curtain on all the taboo stuff nobody talks about. Drug and alcohol addiction. Dealing with the death of loved ones. Recovering from childhood abuse. Cheerful stuff like that.

One of the chapters is called How To End Your Life.


The author started with a chilling description of what it’s like to try to commit suicide. He knows – he’s tried. Given the life he’d had so far, an argument could be made that he had a fairly compelling reason to kill himself, too, so he’s got some credibility with his target market.

He does a pretty good job of convincing people with part-time amateur suicidal tendencies that suicide is not really much of a solution.

And then he goes on to say this:

Ending your life could mean ending your life. But you could accomplish the same end by ending your life.

He talks about realizing that killing himself was not the answer to anything, not because of some puritanical morality, but because it would hurt too much. If you want to end the pain, and all you’ll experience to do so will be pain, you haven’t really succeeded, have you?

He talks about cutting all ties with everyone he knew, changing his name, and moving somewhere completely different.

He ended this life and started a new one.

It took a long time and it was hard and there were times when it didn’t work very well. But frankly, what was the alternative? (We’ll talk about alternatives on Wednesday, by the way.)

So he embarked on a long and difficult and painful journey, full of things that very few of us have the guts to do, and full of things that seem dramatic and counterintuitive and unpleasant and unnecessary. And at the end, he got a newer, better life.

The tweaking bias.

Over the weekend, we talked about the cultural bias towards finishing everything you start. We don’t really have that bias, actually. Not all the way. There are plenty of things we’re allowed to quit. We only have to finish things that the people around us think we should finish.

If you don’t like your salmon and your dining companion agrees with you, you’re allowed to quit that. If you don’t like your job and your spouse agrees with you, you’re allowed to quit that. If you don’t like your husband and your father agrees with you, you’re allowed to quit that.

But if your girlfriend thinks you should finish the salmon, or your husband thinks there’s nothing wrong with your job, or your father thinks your husband’s a stand-up guy, then we have to finish what we start.

That creates a little sub-bias, which is the tweaking bias.

Because we’re not allowed to give up, we have to make tweaks.

My marriage is an unmitigated disaster and my wife has been cheating for the last three years. Maybe I should do the dishes more. Or date nights!

My boss is an abusive despot. Maybe I should go out with my girlfriends more, or take some assertiveness training.

I haven’t made a dime. Maybe I should change my blog theme, or get some new headshots.

That’s a fairly intuitive strategy. It makes sense, given the culture we were born into. Never quit, keep trying, and for God’s sake, don’t do anything dramatic.

But sometimes?

Sometimes you have to break it and start over.

How do you know if that’s what you need to do?

To be fair, you can’t really know it’s time to quit and you can’t really know that the same problems won’t happen again. You can’t ever create the perfect timeline or the perfect checklist, and you can’t predict exactly how crazy everyone’s going to go. (Hint: probably fairly crazy.)

But you can ask the right questions and look at the right data points and set yourself up as well as you can.

I’d like you to think about that for a little while today.

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