Looking back at forty-something, I can see two distinct groups among my peers.
There are those still chasing their tails, wondering why success keeps slipping through their fingers. Then there are those who seem to have it figured out – not because they were born lucky or particularly gifted, but because they made specific investments in their twenties that are paying dividends now.
The difference? It comes down to what they chose to invest in during those crucial early years.
I spent most of my twenties and early thirties in corporate, watching both types up close. The patterns became impossible to ignore. Those who achieved meaningful success by forty weren’t necessarily the smartest or hardest working. They were the ones who understood that certain investments compound over time.
1. They invested in skills that compound
Most twenty-somethings chase the highest salary. The successful ones chase transferable skills instead.
I watched colleagues jump ship for an extra five grand while others stayed put to master skills like public speaking, writing, or data analysis. Guess who’s running companies now versus still job-hopping for incremental raises?
The book “Range” by David Epstein really drove this home for me. He argues that generalists often outperform specialists in complex environments. Those who invested their twenties building a diverse skill stack rather than just climbing one narrow ladder have more options and adaptability now.
Think about it: technical skills might get outdated, but the ability to communicate complex ideas simply pays dividends forever.
Learning how to learn is priceless. Building emotional intelligence when everyone else is focused on technical prowess is what separates leaders from individual contributors.
2. They invested in their health before they needed to
Here’s what nobody tells you: the health habits you build in your twenties determine your energy levels in your forties.
I started taking fitness seriously in my mid-thirties when years of sitting and stress were catching up with me. The climb back was brutal. Meanwhile, friends who established workout routines and healthy eating patterns in their twenties? They’re still running circles around everyone else.
Research published in JAMA Network shows that fitness levels in your twenties and thirties directly predict cardiovascular health decades later. But it’s not just about avoiding disease. It’s about having the energy to capitalize on opportunities when they arrive.
The most successful people I know treat their bodies like high-performance vehicles from day one, not waiting until the check engine light comes on.
3. They invested in relationships, not just networks
Everyone talks about networking, but the real winners invested in genuine relationships.
There’s a difference between collecting business cards and building trust. I’ve seen people with thousands of LinkedIn connections struggle while those with fifty deep relationships thrive.
Why? Because when push comes to shove, people do business with those they trust, not those they’ve met once at a conference.
One friend spent her twenties organizing small dinners for interesting people, no agenda attached. Just good food and conversation. Fifteen years later, those dinner guests have become her advisory board, investors, and closest collaborators.
Robert Putnam’s research on social capital shows that relationship quality, not quantity, predicts both career success and life satisfaction. The relationships you nurture in your twenties become your support system, opportunity pipeline, and sanity check in your forties.
4. They invested in financial literacy early
While everyone else was living paycheck to paycheck, the successful ones were learning about compound interest.
Growing up working-class outside Manchester, money wasn’t something we talked about beyond making ends meet. But those who broke through understood that financial literacy isn’t about being rich – it’s about understanding how money works.
They weren’t necessarily earning more in their twenties. They just understood concepts like emergency funds, index investing, and the true cost of debt. A colleague who started investing just £200 monthly at 25 has over £100,000 now, while another who waited until 35 to start needs to invest triple that amount to catch up.
Real wealth isn’t built through windfalls but through consistent, boring financial habits started early.
5. They invested in experiences over things
The successful forty-somethings I know have incredible stories, not impressive garages.
In their twenties, while others were financing cars they couldn’t afford, these folks were backpacking through Southeast Asia, taking challenging assignments abroad, or saying yes to projects outside their comfort zone.
Research by psychologist Thomas Gilovich confirms that experiences provide more lasting happiness than material possessions. But there’s more to it. Those experiences built resilience, cultural intelligence, and problem-solving abilities that no MBA program could teach.
When I finally left corporate, terrified but determined to build something on my own terms, it was the challenging experiences from my past that gave me confidence, not the safety net of savings alone.
6. They invested in mentorship and coaching
Here’s something I’ve mentioned before but it bears repeating: successful people don’t figure it out alone.
In their twenties, while others were trying to prove they knew everything, the now-successful were actively seeking mentors. They swallowed their pride, asked for help, and learned from others’ mistakes instead of making all their own.
Some paid for coaching when they could barely afford it. Others volunteered for successful people just to be in the room. They understood that learning from someone ten years ahead could save them five years of trial and error.
7. They invested in self-awareness
This might sound soft, but the most successful people I know invested serious time understanding themselves in their twenties.
They took personality assessments seriously, sought feedback actively, and weren’t afraid of therapy. While everyone else was projecting confidence, they were building genuine self-understanding.
Daniel Kahneman’s work on cognitive biases shows how little we understand our own thinking patterns. Those who invested in self-awareness early learned to recognize their blind spots, play to their strengths, and build teams that complement their weaknesses.
By forty, they’re not still figuring out who they are. They’re leveraging that knowledge to maximum effect.
8. They invested time in deep work
In an age of constant distraction, those who learned to focus deeply in their twenties have an almost unfair advantage now.
Cal Newport’s concept of “deep work” – the ability to focus without distraction on cognitively demanding tasks – wasn’t just about productivity. It was about building the mental muscles for sustained concentration.
While others spent their twenties multitasking and responding to every notification, the successful ones were building the ability to think deeply about complex problems. That skill becomes exponentially more valuable as you climb higher and problems become more complex.
The bottom line
Success by forty isn’t about making one right choice. It’s about making consistent investments that compound over time.
The tragedy is that most people treat their twenties as a dress rehearsal, thinking real life starts at thirty. But those who achieve real success understand that the seeds you plant at 25 determine what you harvest at 40.
Don’t worry, even if you’re past your twenties, these investments still pay dividends. The best time to plant a tree was twenty years ago. The second best time is now.
What strikes me most, looking at these patterns, is that none of these investments required special talent or circumstances. Being first in my family to go to university, I thought successful people had some secret formula. Turns out, they just started investing in the right things earlier.
The question isn’t whether you have what it takes. It’s whether you’re willing to make the investments today that your future self will thank you for.