How to Think Like a Millennial

As far as generational differences go, most people have it wrong.

Stereotypes run rampant, information is contradictory, and thought leaders are just guessing.

To be honest, I really didn’t want to write this article for that reason. I don’t want to be lumped in with the rest of the attention-grabbing fluff.

But I keep getting this question at work:

Why are you so different?

It doesn’t come up every day, but often enough that I feel the need to address it.

I don’t think my way of thinking is confined to millennials, nor do I think it’s out of reach for anyone who wants to change his or her life.

I do, however, think it’s a series of intentional steps which may or may not come naturally to you depending on how you were raised.

So let’s get into it:

See yourself as a entrepreneur, not an employee

Try an exercise for me:

Write down every skill you have.

Your first thought will be “I’m not good at anything,” which is fine. We all start there.

Ignore that instinct and start writing: cooking, cleaning, programming, mowing the yard, training dogs. Whatever you’ve got, write it down.

Got your list? Good. Now, out to the side, write down three people who could use each skill you have. Here are a few of mine:

  • Writing: Creative people who need motivation, entrepreneurs who need copy for web pages, Medium (who needs writers to exist)
  • Graphic design: A local business owner, a mom who wants invitations for her child’s birthday party, my co-workers who want to spice up Powerpoints
  • Editing: Writers who can’t see the flaws in their work any more, speakers who need to cut down their talks, online course designers

Go as wide as possible with the amount of skills and then go as deeply as possible with the number of people who could use that skill.

The point of this exercise is not to figure out how to make money off everything you can do, but to quantify your value. Take stock of your abilities, and then find the people who need them.

Think a lot of yourself

One of the biggest differences I find in general between people my age people older than me is that the previous generation has more trouble taking credit for what they do.

The exercise in the last section was not so you could learn to grab credit, but to accept it when you deserve it.

If you’ve ever assumed you are “less than” because you are a certain weight, age, gender, or hold a certain job, please stop it.

Step up and accept the unique and random combination of atoms that is you. It won’t make you prideful. In fact, it will make you grateful — grateful for everything you do have and indifferent about what you don’t.

Do things without asking anyone

You can use a lot of words to describe my generation. “Cautious” is generally not one.

It may have been Tim Ferris when he laid out his “ask for forgiveness, not permission” premise in the 4 Hour Work Week. It may have been in bred into the media we grew up as kids. Heck, it may be natural that we started to think we could do whatever we want since every single thought we put out into the world could get immediate worldwide attention from anyone.

Try something for me. The next time you see a problem which is within your ability to fix, step forward and fix it. Afterwards, you can go and tell your boss what you’ve done.

I think people are afraid they’ll get their wrists slapped for this kind of behavior, but in my experience, the more problems you solve for people, the happier you are.

Warning: an increase in problem solving generally results in more work. Which leads me to the next step:

Do a lot of work

This isn’t particularly a millennial trait. But it’s not something that we are afraid of.

Do you know why a lot of young people try a lot of different things? It’s because we don’t know what we’re good at yet. Our actions look like ADD. In reality, they are just exploration.

If you’re not sure about your path in life, try everything. How else will you know what you like? (and what you don’t).


This is been in easier for our generation then any other. Getting away to a different state country or continent has never been simpler.

You owe it to yourself to get on Airbnb right now to see what kind of deals going on in the next date over. Often you can stay somewhere for 40 or 50 bucks a night. You’d be amazed at what a change of scenery can do for your mindset.

Ignore these excuses:

“I have a family!”

Take them with you

“I can’t take off work to travel!”

Go on a weekend

“I don’t have the money to-”

Go camping

“I can’t stay anywhere overnight!”

Take a day trip.

Here’s the thing — your brain is designed to assimilate and ignore as many things as possible. This includes surroundings. How many times have you driven all the way to work without remembering the process?

When you find yourself in a new area, you don’t have time to stress about work or family or personal crises because your mind has SO many things to process.

Step out and get away from the noise. A little headspace goes a long way.

Step Up, Step Out, Step Forward

If you’re looking for the TL;DR version of this post, here it is:

Step up — even if you don’t have to, don’t know how or don’t want to. Make the decision to rise to every challenge you cross.

Step out — of your comfort zone. A trademark of millennial’s is that we never stand still. The second you start getting bored and comfortable, see that as a red flag.

Step forward — into a life some company with a retirement plan could never give you. From this moment on, own your destiny. Don’t pass the buck to someone else.

Stay focused. Stay balanced. Learn, and most importantly:


Confession: I’ve stolen the “Step Up, Step Out, Step Forward” framework from my good friend Declan Wilson’s book — The Millennial Way.

You can find more about him right here, or hurry over to pick up a copy of the book on Amazon.