3 Years After Blowing Up My Career

Hello again my friend,

Three years ago, I left my job as a director at an stellar agency with great people to pursue my own venture. I wrote about how it was a huge mistake, partly because of my negligence, and partly for factors outside of my control. Regardless, I blew up my career.

The previous post was a recap of what not to do. How not to start a business. How not to lead with ego. How not to sell something unless you’re sure you can deliver (I returned $20,000 in refunds). I made so many mistakes.

The learning came slowly. The growth came harder. But here’s what I’d tell myself now. Today, we get into it.

These are short, condensed lessons I’d give my past self, and I hope they’ll help you too.

Let’s lock in.

You are not obligated to explain yourself to anybody, or give anybody a second chance unless you want to. Them being nice to you doesn’t mean you owe favours. That’s not how it works.

I’ve had many people ask me for money over the years. It’s because they trusted me, and because I was soft. Most never paid me back. Now, I’m firm: kindness is a choice, not a debt. Set boundaries early to save your energy for what matters.

Set boundaries early to save your energy for what matters.

Talk is cheap. You’ve heard this before, and for a good reason. People talk all kinds of shit, and while it’s annoying, there’s a way around this.

How do these people spend their time and money? That’ll tell you everything you need to know. In business, and friendships.

CEOs that take 10 vacations a year are not serious. People who talk smack about others will talk the same smack about you.

How many business people say one thing in an interview and do the complete opposite behind closed doors?

Watch how people treat the people they say they love.

I’d have saved countless headaches and issues if I’d been more serious about this. Some people are great friends, and awful business partners for the same reason. Some people are brutal in dating, but great in business.

What matters is the pattern of behaviour.

There’s an imaginary line. On one end of the line, you have greatness. On the other, you have disgusting. Human beings fall somewhere on this line, and are good or bad to varying degrees. Some days they’re awesome. Other days, awful. To think of people as just “good” or just “bad” misses the point.

I’ve had people be nice to me for a few months, and then ask me for money. There’s a sob story, and they’ll tell me they’ll pay me back. Turns out they have a secret gambling problem. On the flip side, a guy I got into a fist fight with in middle school ended up becoming a good friend through high school. Still is.

People can be great in business, and awful in personal relationships, or the reverse.

Some people will be nice to you today, and still disappoint you tomorrow. Patterns matter more than peaks.

Not everything has to be a big deal. But when it is, fight hard for what you believe, and don’t take no for an answer. It was one of my proudest moments the first time I did.

Many years ago, I worked for an agency in Vancouver as my first corporate job out of school. I was in sales. I did well. Fast forward; after closing about two million dollars for this company, the owner tried to rip me off on my last cheque.

I’d resigned after some issues in the business (poor money management, layoffs, etc). I looked at the last cheque when he handed it to me, and it was short. Mind you, it wasn’t much money. It was like $5,000. But the principle bothered me so much I couldn’t let it go.

I told everyone at the office. I’d closed deals previously for his business partners, and told them too. I threatened that if I didn’t get my money I’d be going to every client I’d ever closed for all of them with a lot to say.

It didn’t matter if it was $50k, $5k, for just $5. The line was crossed.

A couple weeks later, the money was paid in full.

I’d let a lot of things go before that. Sleepless nights, doing a million things that were someone else's job. Covering for the CEO. Those were annoying, but I sucked it up. But this….was too much. To this day, I’ve never regretted it.

Not everything has to be a fight. But if you’re going to fight, fight to win.

But what about all those little things that add up? How long do you let them go before you say something? Before you stand up and say no?

It’s easy to fall into this trap. One person asks for a favour. Then another. Before you know it, you’re strung along on time-wasting nonsense. “No more Mr. (or Mrs.) nice guy” is a real thing.

It’s come up countless times.

It’s better to be nice to the person and hard on the details. You can say no. Most people should expect it when they’re acquaintances asking for favours.

If a friend is not willing to deal with a minor inconvenience for you, they’re not your friends. They are acquaintances. And that’s okay. Just treat them the same way.

In Persian culture, we have this idea of Tarof. A kind of etiquette emphasizing politeness, mutual deference, and self-lowering to elevate another person. Many cultures have something like this. I would write an entire post dedicated to this, but that’s for another time.

Tarof involves a subtle dance of words and actions where people "fight for the lower hand," which can manifest as refusing an offer you actually want or insisting on paying a bill, even when you don't want to. The goal is to show respect, foster goodwill, and manage social relations.

Many of us can’t stand it. It’s just such an old tradition that it’s invaded almost all parts of life. There’s no getting away from it in our culture. But, it should stay in our culture. Applying these principles in other parts of life, especially business, just creates confusion. Other people don’t get it, so they continue as they were, and we’re elevating others, but they’re not returning the favour.

Cutting all of this was an instant game changer.

Foster relationships, but remember that the customs in your culture may not belong in your business context.

Waiting for good things without any action leads to disaster.

I’ve had so many cases where I sit around and wait for that raise, promotion, or something else. Whatever it might be. But great things don’t work that way. You have to make these things happen. What comes from you comes back at you, and if you’re working hard and doing well, push for what you want early and often.

When first learning how to sell, there’s an expression used to go from an order taker to a closer. Ask for the sale.

Learning how to sell and negotiate was one of the best things I ever did. Asking for what you want leads to rejection, which is fine. If you make $100K and ask for $120K, the worst they’ll say is no, and you’ll still have your $100K.

I was once given a bonus cheque. I expressed great thanks because it was never negotiated. I was thankful, and I made it clear. They did a nice thing for me, what’s wrong with that, right? I looked at the cheque. It was for $1,000. I closed double my quota that month. If I’d actually negotiated a bonus, it would have been at least ten times that.

So what did I just do? I just showed these people that I’d be happy and thankful with $1,000. Imagine their surprise when it was time to negotiate my raise and they were low-balling me. You get the idea. You may deserve a lot of money, that doesn’t mean they’ll just hand it to you.

Waiting around is never the answer.

Ever had someone takes weeks to get back to you, and then feel offended if you took a few days to reply?

Have there been times when you go out with friends, yet you’re somehow paying the bill more often than the others?

I try not to keep score, and I’ve been this way for many, many years. But something interesting happened. I explained this to someone. They told me, “I only keep score with certain people.”

This struck me as odd. Why only certain people?

I realized then. If I actually kept score, a lot of people would ‘owe’ me. I’d be losing in so many situations. Keeping score is a bad habit. But ignoring how other people keep score, and play to win, is a bigger mistake.

Especially if you’re a thinker.

There’s always a reason not to ask for the raise, not to bet on yourself, not to take that shot. Do it anyway.

Now, you may lack the confidence to do it. That’s okay. I’ll break it down for you.

It may seem ironic now. But if I’ve learned anything, it’s that most advice sucks. Good advice may not always fit your context. And good advice that genuinely could work for you, it’s not your only good option.

Do what you want and bet on yourself anyway.

Thanks for reading.