What ~100 People Wish They’d Known at 25 About Careers

What’s around the river-bend? No idea. And there’s no way of figuring it out.

Preface: In the winter of 2015, I realized I was about to hit my mid-20s with only a few incongruent career jumps and a rapidly failing relationship to show for it. The hackneyed quarter-life crisis ensued.

I started asking interesting people what they wish they had known when they were 25 years old. Then I started blogging about it. The answers, close to 100 in total, came from all walks of life: Uber Drivers to college professors to vagabonds to millionaires. Some submitted advice through the blog website, some were formal interviews, and some were be spontaneous conversations that were never chronicled.

5 years later as I turn 26, I’m rounding up the best wisdom that came out of these conversations. This is Part II: Careers.

Take jobs based on learning opportunities, not the particulars of what you do.

Contrary to the millennial expectations with which you’ve been raised, your job right now is probably not perfect. That’s ok. The people who are amazing at anything did some shit aspects of a job, which ultimately taught them how to be better at what they do now.

One of the wealthiest people I interviewed for this blog (who will ultimately never agree to let me publish with his name) will remember a great weight of anxiety around this time. He was doing consulting work and felt as lost as he did miserable. He would end up going to grad school to justify making progress in his career (which he strongly advises against). His thought on what he wishes he knew at 25 sums this up well —

“People’s trajectory changes all the time. The next six months are not the next six years. Even then, you might spend six years doing something, but it’s not necessarily carved in stone. It’s the “zoom out” advice. As long as you’re working hard and challenging yourself it’s ok to be stressed out… The purpose of your job is not to feel comfortable. It’s to challenge yourself to be better. Go find a tough job and just stick with it.

Thus, don’t lose your head about one specific path, an arbitrary milestone or whether your friend’s job on Facebook looks fleetingly more glamourous. Look for ways to learn within your current role, even if they weren’t what you were expecting. If there’s no more chance for learning, leave. That way, no matter what unpredictable paths life takes, you’ll have the confidence, skills, and experiences to adapt to new realities.

Take an hour a day and one day a week for yourself — no matter what.

Mental health is important, and like all other areas of health it doesn’t come for free.

There’s two parts to this. The first is prioritization. Exhaustion and busyness aren’t signs of how successful you are. Cocktails are great, but you can’t fill one glass with five different kinds — You’ll just end up making a mess on the floor. Choose 2–3 things that resonate with you and matter deeply, and focus on them.

Second, figure out through experimentation what recharges you. Perhaps an entire day per week to stop checking email and self-care. Many Boulderites suggest frequent bike rides. Consider therapy, even if you don’t think you need it. Those things are important and positive and will make you more effective at work anyway.

You can figure anything out.

If you’re frequently pushing your limits, you may hit stretches where you feel uncomfortable and weak. Press into those stretches. Come out of them more confident than you were before in your ability to push your limits.

This is the time in most career articles where they drop the, “don’t be afraid to fail” bomb. It’s trite, but it’s overused for a reason — because hugely successful people follow that adage. Unfortunately, failure (despite all the hash-tagging and glamour that startups associate it with), can be devastating. You do have a financial future to think about, so maxing out your credit cards to start a company is probably a bad idea. With that in mind, perhaps an alternative could be: “Take intelligent risks: Know that failure might happen, hate that idea, accept that it’s worth the ride, but don’t put so much at stake that you can’t get back up again.”

The good news is, when we’re young there’s very little we can’t bounce back from. So take (most of) the leap(s). View challenges not as burdens but as tests. Go after things as though you already know you have a great chance of figuring it out.

Andrew Hyde, Founder of Startup Weekend and Startup Week, learned this lesson young:

“If you don’t own it, you never will. Someone told me that at my first ever job bussing tables at 16. It’s both internal and external. If you don’t truly believe that you’ll succeed at something, you only hold yourself back. You won’t push as hard. Others will see you aren’t pushing and they won’t invest in you either. If you don’t act with the pride of ownership you never will get the chance to own anything.”

When you hit a road block, experiment or ask someone for help. As Krista Morgan, CEO of P2Binvestor said

“I just had to get to a certain place where I don’t question that I’m the best CEO for P2Bi. That doesn’t mean I have all the answers. As long as I’m listening and learning and questioning and moving forward we’ll get there. That feels less 100% on my shoulders. I feel less like our success depends on me knowing everything. And that’s a big change from my 20s to 30s.”

Yes, we are young and inexperienced and flawed and to think otherwise is based in arrogance. On the other hand, you will never know everything. You are not perfect. You never will be. No one is. But if you’re willing to listen and like the thrill of a challenge, you can figure almost anything out one step at a time.