What I would tell my 21-year-old self

“Robbie, I would recommend that you don’t call yourself a Junior Analyst in your email signature. You can just call yourself an Analyst.”

“OK. But when I become CEO, I’ll make sure my signature says CEO!”

This email exchange was me foolishly believing I was going to be the CEO of a multi-billion dollar company.

15 years later, the thought of running a multi-billion dollar company is not only outlandish, but I’m 110% sure I never want to have that job.

Expectations as a 21-year-old vs. reality change as you progress through your career.

Here is everything I would tell my 21-year-old self.

Your career is not a straight line. Sometimes it feels like a circle.

You’re going to wonder how in the world you got so far from your original plan.

If you follow the money, you’ll end up with more money but farther from where you want to be with your career.

If you follow your passion, you’ll end up with no money and a little bit closer to where you want to be.

If you figure out a way to merge a way to make money & do something you’re good at, your life will be better.

Start budgeting right now. No, seriously, right now.

Start writing. I know you’re not good at it. But, just do it anyway.

You’re going to become good at what you do, and others are going to ask you to join their team. They are going to ask you to make life changes to help them. Make sure that life change is part of your plan, and not just theirs.

Don’t listen to those people who tell you to say no to everything. You can only say no once you figure out what you want to do with your life. Say “YES” and see where it takes you.

You’re going to ask yourself if you should apply to a startup called “Facebook” in 2007. You’re also going to tell yourself that the company is too late stage for you to make any money. Don’t listen to that voice. Your voice is stupid.

This thing called “Bitcoin” is going to come up once in a while. You’re going to think to yourself “That sounds too complicated, I’m not going to buy bitcoin for 22 cents.”. Don’t listen to that voice. Your voice is stupid.

Your instinct about traveling is right. Do it now before it’s too late.

Money doesn’t buy happiness, but if you have just enough in your bank account at any given time, you won’t have to make decisions that make it harder to live life.

Don’t pick up the phone when you’re sleeping. It’s a phone interview at Google you hustled to get. You’re not a good at pretending you’ve been up the whole time.

Don’t nap before phone interviews.

Use an alarm clock even when you’re napping.

An interviewer is going to ask you who your worst manager was. Don’t answer that question. It’s a trap.

You can think more than a few years ahead at a time. I promise it will come faster than you think.

Sometimes it’s ok to help yourself before others.

If you take more than five deep breaths before you get to work, you need a new job.

If you check your email before work and you swear more than five times, you need a new job.

You need a new job.

Yes. You can go to your friend’s BBQ. You don’t need to work every weekend. It will be OK.

Find the cubicle that is closest to the exit so you can leave work early without anyone noticing.

Real life is going to get in the way of success. Embrace it.

“It is what it is” will go from being a meaningless quote to your life’s motto seemingly overnight.

Don’t worry when you post your writing online. Post it as soon as you finish it.

21 Year Old Robbie: Even if it’s a Friday afternoon and no one will read it?
35 Year Old Robbie: Even better.

What would you say to your 21-year-old self?

PS: Read the only resignation letter template you’ll ever need.