What 100 Coffee Chats Taught Me About How To Live My Life In My Early 20s

4 motivational takeaways

Photo by Sam Lion: https://www.pexels.com/photo/positive-asian-women-chatting-and-enjoying-hot-drinks-on-street-5709253/

At 22 years old, I worked in Washington DC for the federal government under the Obama administration, and nothing made me feel more powerful.

Surrounded by smart, dedicated people full of career-related purpose, I felt empowered to live out my dreams.

Anything was possible.

Sadly, I worked on a short-term contract, so I’d have to land something quickly lest I risk unemployment.

I was laser-focused to get my foot in the door to any place in my field that would have me. And if there’s one thing I learned in college, it’s that my next opportunity could be one coffee chat, one contact, one networking call away.

So my mission became to meet two new people each week to ask them questions that would help me narrow down a mutual fit for my next move.

How did you get to where you are now?

What do you do and what do you like or dislike about it?

What is one thing you’re glad you did in your 20s so I could do it too?

I was, and still am, incredibly grateful for every single conversation.

In total, I spoke with 135 people within 6–8 months. I documented each contact and takeaway in a detailed (and protected) Excel spreadsheet, including their name, title, and institution, down to which people had the kindness to buy me a coffee, despite how I was the one who asked for their time so that I could return the favor one day.

Many years later, I’m finally sharing the takeaways that resonated with me the most.

Here’s what I learned from over 100 coffee chats when I was 22 years old.

From a disillusioned middle-aged man

If you’re not careful, you can “fall into” a career. You can go with the flow for long enough until one day, you wake up and realize that what you’re doing now is no longer what you want to be doing. You’ll wonder how you got here, and you can get stuck if you’re not mindful.

I was a bit shaken, to be honest. Despite it being almost inevitable, human even, his rut struck me as something to avoid or prevent by being intentional with my choices.

At 22, I hadn’t considered how people could still be figuring it out well into middle age.

At 22, I felt like you could do and be anything you wanted, and to some extent, that still holds true.

Until you have kids and depending on who you marry, your decisions on work and career become more calculated. Less risky.


What you do now matters. Because, well, in more cases than not, it can influence what you’re doing 5, 10, or even 20 years from now, and if you’re not careful, you can get stuck.

What can you do about it?

Define and align with your values. Those can shift over time, and that’s okay.

From a recent grad not much older than me

If you hate trading stocks in Chicago, you can quit, even in the first 6 months.

You can pack your bags and move to Silicon Valley, learn to code, land a job in software. Join a startup. Build your skills. Jump to a bigger tech company, and wash, rinse, repeat.


You don’t have to chip away at anything you don’t want to. You can pursue alternate life paths through drastic changes like my friend here or through slow and consistent changes.


Get and stay focused. Above all else, minimize regrets and don’t feel like you have to sacrifice anything you can’t get back.

From a financial services leader

At the time of this conversation, I considered the big consulting firms that recruited on campus to lure in eager, analytical, and perhaps some naive minds.

She encouraged me to sit in the front row, be front and center, raise my hand, and get after it.

The competition gets overwhelming when you feel like a lemming doing what other lemmings do. While I ultimately excused myself from that route, the advice still resonated.


Be fearless, assertive, and unapologetic in your pursuits. Whatever it is you want, grab it without holding back.

Side note.

Nothing will prepare you for the stress of being responsible for calling the shots in an ambiguous, risky, fast-paced environment with high stakes involved, like millions of real dollars and people’s jobs.

Even the pressure that molded you at one of the top, most rigorous universities in the country won’t prepare you.

From a private sector turned public sector mom

Everything has a season.

At the start of your career, aim for brand name companies that attract top talent. Grind it out and pay your dues. Build your network, credibility, and reputation.

Nothing says “smart” and “qualified” like a household name, am I right?

Doors will open down the line.

Once you start a family, find options that support the working parent lifestyle.


Practical, grounded advice rooted in reality. 

My nature to go against the grain had a hard time reconciling with this tried-and-true formula.

Did I still follow it? Somewhat, not really. 

Do I regret it? No.

Closing Thoughts

After 100+ coffee chats, I can confirm one thing we all know to be true.

Everyone has a story to tell. Everyone wants to feel heard. Everyone wants to feel important in some way.

If I could make someone feel like their work and insights matter, even for 20 minutes over a stale government coffee, I feel good knowing I ever asked at all.

And to all those who gave me their time to share their experience, thank you. I see you, I remember, and I am forever grateful.

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