If I Had to Start Over at 21 (In the Age of AI)

Fair warning: this entire post could be obsolete in six months with how fast things are changing.

But that's kind of the point.

If I could go back to 21-year-old me, standing in my tiny apartment in Toronto with big dreams and no clear path, what would I tell her?

I made a lot of good calls and a lot of bad ones. Starting again, I'd leave less up to chance, and I'd factor in something that didn't exist when I was 21: AI is fundamentally reshaping how we work.

Yes, everything is changing. And there is no doubt that the playbook that worked for millennials or even older Gen Z won't work now.

Matt Shumer, an AI startup founder, recently wrote a piece called "Something Big Is Happening" that's been making the rounds. He describes realizing he could describe what he wanted built in plain English, walk away for four hours, and come back to the finished product.

Worth reading, but I think the "every job is disappearing" framing is too extreme. On one end, Goldman Sachs estimates AI could affect 300 million jobs globally, and Anthropic's CEO Dario Amodei has warned that half of entry-level white-collar jobs could vanish within five years. On the other end, Elon Musk is telling people at Davos that AI will create "an explosion in the global economy beyond all precedent", a world of such abundance that saving for retirement won't even matter.

The answer is somewhere in the middle. Not every job is going away, but jobs are being rewritten.

Case in point: IBM just announced it's tripling entry-level hiring in 2026. Their CHRO put it bluntly: "The entry-level jobs that you had two to three years ago, AI can do most of them. You have to rewrite every job." Their junior developers now spend less time coding and more time with customers, building new products, and overseeing AI outputs. Dropbox is expanding its internship and new grad programs by 25% because younger workers are more comfortable with AI than their older colleagues.

It's not "AI replaces you." It's "AI changes what's valuable about you."

When I became a lobbyist for Silicon Valley tech companies, working with politicians and CEOs required me to grapple with my imposter syndrome immediately.

I remember standing at a podium, speaking to a group of important people, and tripping up on a few words. Into the microphone, I uttered "oops, I messed up already."

After my speech, my husband said: "You know, if you hadn't said anything, no one would have noticed."

I thought I needed to "make it" first. But nobody needs another highlight reel. They need the messy middle. I was forced to show up every day and make myself 1% better, 1% more credible every time I spoke.

When AI can generate polished content in seconds, your authentic voice and real experience become even more valuable. I wish I had built in public like the younger Gen Z founders are from the beginning. It's a big benefit they have and everyone should take advantage of it. And here's something worth remembering: when the cost of technology drops to zero, it is distribution that will be queen. The people who build audiences now will have the ultimate advantage later. Climb Cringe Mountain, and trust the process.

If I were 21 today, I would spend one hour a day experimenting with AI tools, not reading about them, but using them for real work.

As Shumer writes, the person who walks into a meeting and says "I used AI to do this analysis in an hour instead of three days" is the most valuable person in the room.

But here's where I disagree with the doomsday crowd: AI still doesn't have discernment. It doesn't have taste. It can't walk into a room, read the energy, and know which idea to kill and which to double down on. That's human judgment, and it's what separates good work from great work. The combination of your expertise and AI fluency is what makes you powerful.

That's why IBM is hiring more entry-level people because AI still needs human judgment, customer empathy, and creative problem-solving to work in the real world. Dropbox is expanding its internship program by 25% for the same reason.

The future isn't human vs. AI. It's humans who use AI vs. humans who don't.

When my husband and I got married in our early 20s, we were both in debt. I had school debt and he had credit card debt.

My nerdy husband (God bless him) became obsessed with tracking every penny on a spreadsheet. He said it was satisfying to watch the debt shrink. Then it became satisfying to watch our savings grow. Then investing became an addiction.

No one told us it takes a decade for compound returns to become meaningful. The money you invest in your 20s does the heavy lifting in your 30s and 40s.

We're not alone. According to JPMorgan Chase Institute data, the share of 26-year-olds investing jumped from 8% in 2015 to 40% in 2025. Gen Z is increasingly choosing stocks over homes because the math often works out in their favor.

It's not about the money, it's about freedom. Investing in our 20s is the reason my husband and I are both home with our child today. For most Americans, paid parental leave isn't an option. If you want the freedom to take time off for the things that matter most, like having kids, starting a business, or navigating a career transition, you have to build that safety net yourself.

Live below your means. Aggressively save the rest.

Spending money on yourself is worth it if you do it the right way.

I'm not talking about cars, clothes, or spa days. In 2026, I'm not even talking about a college education.

Coaches. Courses. Books. Masterminds. Learn how businesses work. Take a course on corporate finance. Learn how to use AI tools. The best tutor in the world is now $20 a month, infinitely patient and available 24/7.

Nobody gets to become an expert and coast. The biggest mistake you can make early on is assuming you know enough.

And invest in where you live. Being in a dynamic city like San Francisco, New York, or Los Angeles puts you in rooms you'd never find in a smaller market. The conversations at dinners, events, and coffee shops in these cities shape how you think, raise your ambition, and introduce you to mentors you didn't know you were looking for. You can build a network from anywhere, but there's no substitute for being physically surrounded by people building at the highest level.

If you put yourself out there, mentorship will come your way. When I first started lobbying for Silicon Valley, I had the opportunity to learn from the father of angel investing, Ron Conway.

I learned from Ron by watching how he worked, how he interacted with people, and how he closed deals. It was never formal, but having exposure to how someone operates goes a long way in your 20s.

Not all mentors are people we look up to (has anyone seen Whiplash?). My husband's greatest mentors included people he didn't like. He'd tell me, "Now I know what kind of man I don't want to be."

Learning deeply from a handful of people will help you grow much more than 500 casual connections on LinkedIn. And give back generously to the people who help you. Share your own network, make introductions, find ways to add value to their world too. Make everything a win-win.

To this day, I still reach out to people in my network and ask to meet so I can learn from them. My tip? I always offer to pay for the call. It makes people feel valued and they know you're serious about their time. And 99% of the time, they're happy to do the call for free.

This is the most important career advice I can give right now, especially in the age of AI.

AI is the ultimate generalist: decent copy, passable analysis, serviceable code, reasonable first drafts of almost anything. If you're competing with AI on breadth, you will lose. But AI cannot go deep. It doesn't have the years of context, the hard-won pattern recognition, or the relationships that come from being embedded in a specific world.

Find something you enjoy and become the go-to expert in a subset of that field. You enjoy marketing? What kind? Creator marketing? Master the specific skillset that helps businesses create stellar content when they partner with creators.

When you specialize, people and businesses with a specific need will only find a few experts, and you'll be one of them. You can charge more, you develop real taste and discernment, and you become the person who knows how to apply AI within that niche better than anyone.

AI can give you a decent first draft. Specialists know why the first draft is wrong.

As you specialize, keep an eye on macro trends. What's happening in tech? Where are companies struggling? What's popping up that people are scrambling to figure out?

The smartest people I know aren't fighting uphill, they're riding tailwinds.

If I was 21 today, I'd ask which markets are at the beginning of explosive growth. AI? Climate? Creator economy? Then I'd go there early, learn everything, and build relationships before everyone else showed up.

Pay attention to where big companies are investing. IBM tripling entry-level hiring while redesigning those roles around AI tells us the future belongs to people who work with these tools, not against them.

If I was 21 and starting over, here’s what I’d do right now:

→ Start the thing today, ship before you feel ready.
→ Pick what genuinely interests you over what sounds impressive on a resume.
→ Go deep in one niche instead of being decent at five things.
→ Move to where the action is, even if it's uncomfortable.
→ Build 5–10 real relationships instead of collecting 500 shallow ones.
→ Spend one hour a day using AI tools on real work, not just reading about them .
→ Invest early and aggressively, your future freedom depends on it.
→ Treat AI as your career accelerator, not your replacement.

The path won't be linear, and it shouldn't be. My path from small-town Canada to Silicon Valley to raising a fund to building a media company doesn't make sense on paper. The zigzags are what created my unique combination of skills: the weird opportunities I said yes to, the pivots that made no sense at the time.

We're living through one of the biggest shifts in how work gets done. Shumer compares this moment to the early days of COVID, and I think he's right about the magnitude. Where I push back is on the idea that this is purely something to fear. Companies like IBM and Dropbox are showing us that AI creates new roles and new paths. The people who will thrive are the specialists who bring real taste, judgment, and depth to work that AI can only approximate

If I could go back, I'd take the same big swings, just smarter, faster, and bolder. And I'd make sure I was the best in the world at one thing, not pretty good at ten.

What would you do differently if you were starting over at 21? Hit reply and tell me. I read every response.

P.S. Know someone in their 20s trying to figure out the path forward? Send this to them.

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