Lessons learned from a Millenial elder statesman

Willis F Jackson III
5 min readMar 1, 2016

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Posts from Talia Jane, Stefanie Williams, and the discussion surrounding these posts have inspired this piece. It is not meant to be a direct response to those posts.

I have struggled with the idea that I am a Millenial for years. Because I am older than 95% of my peers, it seems like I am always having different experiences than them. The last few weeks, I have decided to embrace that difference.

Despite the fact that I am 32, I have so much in common with the Millenial expectation for how the world should work.

Like most of you, I grew up with participation medals, the idea that I can be anything I want, and the idea that everyone is special. I learned to value teamwork, getting everyone involved, and valuing the contributions we can each make.

Unlike most of you, I also grew up with two active duty army officers as parents. I moved to a new place every 3 years and saw most of the US before I graduated high school.

What follows are the lessons I have learned while trying to find my way in the world.

The world is a brutal place

We are all special in our own ways. But the world doesn’t care about that. It doesn’t care about us. If you get lost in the woods and attacked by a bear, it won’t stop because you are special.

It’s easy to get lost in society today, and there are plenty of bear-like people that will take advantage of you.

As much as we have tried to change the world to be more accepting, more honest, and more genuine, it’s still animalistic. If you don’t look out for yourself, you will be taken advantage of.

Something is only worth what someone will pay you for it

There are only two things that impact what you get paid for something:

  • the value of the thing to the purchaser
  • the relative negotiating ability of the involved parties

If you want to get paid more, you have to develop a skill that is worth more to your employer (or whomever pays you). They won’t come give you a raise just because you got better, even though I think they should.

Establish what your work results are worth to them, and then make an argument to be compensated based on that value you are providing.

When I was a kid, my parents went to buy a new van for all of our long driving trips. We looked at one that had a TV and a Nintendo built into it. I was in love.

My parents walked out of the dealership 3 times while trying to negotiate for that van. I wanted it so bad that I was a complete emotional wreck. After my parents got the price they wanted, I asked why they kept walking out. It turns out that if you only learn one thing about negotiating, it should be this. If you are willing to walk away from a deal, you greatly improve your position in a negotiation.

I know that it sucks. There are times where I don’t want to walk away, but I know that if I don’t then I will be taking an unfair deal.

Lastly, never get jealous of people who make more. Remember, if you remove negotiating skill from the equation, everyone gets paid what they are worth.

Personal responsibility will set you free

Everything I get in life is down to me. If I am going to make progress, it’s up to me to get there. Not everything in life is under my control, but I can influence almost everything that I care about.

When things aren’t going my way, I ask myself what I can do differently? What could I do that I am not doing?

Knowing that I can always do something to make progress towards my goals has made me a much happier person. Progress, improvement, better is always possible. All I have to do is jump in.

Proactive people succeed

Proactivity has many names: hustle, initiative, self-starter, action-bias. They all get to the same core idea. The person that gets stuff done will win out more often than not.

Don’t wait for someone to give you permission to try something. Figure out what you want to do and try it.

This was a hard lesson for me to learn. I really preferred to get people involved in my ideas earlier and to try things as a team. As much as I like this way of working, it doesn’t fit in most companies.

It’s much easier to try something yourself and involve others when it starts to work well. Be a proactive individual and build teams when things start working.

Get a little bit better every day

The key to getting what I want is in making small improvements every single day. This is the process I follow:

  • Remember that failure is part of how we learn
  • Don’t give up
  • Analyze the failure
  • Stop, start, or change something
  • Try again
  • Stay focused on improving

Companies are just barely good enough

This lesson only became clear to me after starting my own company, and it changed how I viewed every experience I had working for other people.

Most companies have goals, and those goals become goals for people at various levels of the company. Building, growing, improving, and surviving as a company is extremely difficult. Generating enough revenue to account for all of the things that need to be done while still having some profit left over is a huge challenge.

Because of the level of difficulty, most companies have to try several things in order to accomplish their goals. When they figure out something that works, it’s usually barely good enough to meet the objective.

When you look at every company as barely good enough to be what it wants to be, you can see the poorly done things for what they are. It’s not intentional, it’s not ignorance, it’s just not important enough to prevent the company from being what it wants to be right now.

So what do you do when you are dealing with terrible stuff in a company? Be proactive. Try to fix it. When it starts to work, rally people to your cause. Then show the company how you are contributing value and negotiate for what you are worth.

You really can be anything you want to be

Our parents, teachers, coaches, and friends taught us that we can be anything we want to be. In lots of ways they were right, but they didn’t give us the whole story.

We can be anything we are willing to work for. Wanting to be something isn’t enough.

We can be anything we are willing to sacrifice for. Working for something isn’t enough.

We can be anything we are willing to suffer for. Sacrificing for something isn’t enough.

You are unique and you can be anything you want to be. But there are hundreds, thousands, millions of other unique people that want to be the same thing. Who is willing to work the hardest for it? Who is willing to sacrifice the most? Who is willing to suffer for success?

I encourage each of my fellow Millenials to keep fighting for what we believe in. Learn, grow, and we can make the change we want to see in the world. It won’t be easy, but it will be fulfilling.

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Willis F Jackson III

I run product. I try to be good at it. I have opinions about how it should be done.