What ~100 People Wish They’d Known at 25 About the Pursuit of Happiness

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 III: Pursuit of Happiness.


Stop spending your money on stupid shit and start putting some away. Some suggest a generous 50%, some say to max out your 401k, but make it at least 15%. Understand finance. It’s easy to justify adventures and spending as, “you’re only young once!” but the longer your money is in the market, the greater the effect of compounding. There will be a day when you can’t work anymore or just want the freedom not to.

Janet, a former global CMO approaching the late stages of her career, says:

“I think it’s about deciding what freedom means to you, and what that implies from a financial perspective. I have respectable assets, I’m going to sit down with my financial planner and figure out how life could be if I just live on what I have. ​But I should have thought younger about what it’s going to take for me to be happy and what does that translate to from a financial picture. It’s that combo of marrying your personal goals and passions with the kind of lifestyle you’re going to have…
I’m mentoring another young woman about your age. Graduated Barnard, very smart, very sensitive and capable person. She is working right now at an animal shelter. Because animals are her passion. She’s so smart and talented and she’s making $12/hour. I’d like her to think a little more ahead to what she needs in 10 years.”

Somewhere along my journey, I was bike touring in the Eastern Sierra and ended up crashing with a mysterious man in Lake Tahoe named Dave. He told me the story of starting his own business. He worked every day for years to get things going. Something to do with math tutoring. The business venture didn’t seem to justify the woodsy castle in Tahoe where he now dwells. Dave explained,

“Make sure that when you’re done, you can just be done. I saved all the money and was building this place up on the weekends. I mean it was a shit-hole when I bought it. But then when I left my business, I came up here and had it all."

As his reward for saving, Dave now gets to chill in his Tahoe mansion and raise rare breeds of ducks. Why rare breeds of ducks? Why not chickens? Why not pure-bred kittens? None of your business — and it wouldn’t matter to Dave if it were. He has enough money to need neither your business nor your approval.

Move West.

Or south or east. The actual direction doesn’t matter. What matters is that if you’re ever going to move, now’s the time to do it.

If your current community means more to you than anything else, then stay. But be intentional about it. Consciously or not, you’re building your future every day. You’re going to date and perhaps marry different kinds of people depending on where you settle. If you produce offspring, they will likely stay in the area they were created. If you want to start a company or work in sales, it’s easier in a place you’ve been for a long time. Don’t waste any more time in a place where you don’t see yourself in 10 years.

Find your sense of belonging.

Several of the people who answer my “what do you wish you’d known at 25” question talked about seeking something or filling the “hole in the soul.” They turned to to alcohol, drugs or aimless wanderings along the journey.

All of them named a different ‘answer’ to the void. Some people found religious texts (literally) and divine grace, some people found a group or community to be a part of, some people built their own communities. The common theme I’ve draw out of it is sense of belonging.

As Mark from Fresno shared:

“Take the time to develop rituals in your life. When our oldest kid moved out, [my wife] Connie was worried she’d be lonely and unhappy. So she started this ritual where every third Thursday, she makes a giant pot of soup and invites all our neighbors and friends over to share the soup. It’s a low-cost thing. It’s low commitment. Our neighbors know they can come late, or not stay very long. And it’s great every time.”

Shortly after starting this blog, I moved suddenly and unexpectedly to Colorado. I knew no one. I copied Mark and Connie’s idea and started a monthly “soup night,” inviting over my meager number of friends and acquaintances and fed them. Eventually the number of attendees grew. Soup Night served as an excuse to move someone from the “we talked once” category to the “mild friend” category. I started feeling deeply fulfilled — happier than I ever had before. This is largely inexplicable as not much changed in my career. One day it clicked: I finally found a group of people who ‘get’ me. That’s made all the difference.