Lessons from the Ladder

Not long ago, I asked hundreds of professionals a simple question: If you could change one thing about your career, what would it be? Their responses came from across industries, generations, and geographies—but the wisdom that surfaced was universal. It wasn’t about money, titles, or corner offices. It was about something deeper: meaning, growth, and courage.

1. The Courage to Move Sooner

Many respondents said they stayed too long in roles where they weren’t valued. One wrote, “I would have changed jobs earlier when it was clear my manager didn’t value me.” Another added, “Believing that your employer will recognize your value and reward it commensurately is the biggest mistake.”

Their advice was clear—don’t confuse loyalty with inertia. Growth rarely happens inside comfort zones. The best careers evolve through motion, not maintenance.

2. Take More Risks—Especially Early

Again and again, people said, “I wish I had taken more risks early in my career.” Whether it was starting a business, working abroad, or changing industries, many admitted they let fear masquerade as prudence. One respondent captured it beautifully: “I’d have navigated it with more of a plan.”

Aristotle once said that courage is the first of the virtues because it makes all others possible. Risk, properly managed, is not recklessness—it’s a declaration of belief in your own potential.

3. Seek Mentorship and Networks

A consistent theme was the importance of mentors—those who see your strengths before you fully do. “I would like to have a mentor who followed the same career path as me,” said one. Another shared, “I should have been more active in replacing my sponsors as others retired.”
Alongside mentorship came networking: “Develop your network as soon as possible.” “Learn to build relationships with leaders.” It turns out that the most successful people aren’t necessarily the smartest - they’re the most connected. Opportunity travels fastest through relationships.

4. Broaden Your Base

Several professionals wished they had built a wider set of experiences—more breadth across roles, industries, and geographies. “I would have gotten into operational roles to broaden my base,” one said. Another reflected, “I’m too early in my career to know, but I want to get diverse experiences.”
The lesson? Careers are portfolios, not pipelines. Depth matters—but so does range. In an age where industries shift overnight, adaptability is the new currency.

5. Focus on the Human Side

Beyond strategy and skill, many respondents spoke about the “people side” of leadership. One noted, “I wish I had more training in human psychology early in my career.” Another wrote, “I’d focus more on people development.”
Technical mastery may open doors, but emotional intelligence keeps them open. Leadership is not simply managing projects—it’s understanding people.

6. Invest in Yourself First

A quiet but powerful insight came from those who said they’d “prioritized self-development earlier.” Several mentioned learning negotiation skills sooner—not to win more arguments, but to “be empathetic and help others.”
The most fulfilled professionals realize that self-investment compounds. Books, courses, reflection, and coaching are not luxuries; they are fuel. When you grow, everything around you grows.

7. Don’t Lose Sight of Connection

In a post-pandemic world, people reflected deeply on the isolation of remote work. One wrote, “It’s hard to meet new folks when we’re all remote.” Another longed for “more team engagement” and “a hybrid environment to reconnect.”
Human connection remains the heartbeat of work. The best moments in our careers are not metrics—they’re memories. Laughter in the breakroom. A shared win. A mentor’s encouragement.

8. Anchor to Purpose

Perhaps the most striking answers came from those who simply said, “Nothing—I wouldn’t change a thing.” These were people whose careers aligned with their values, who found meaning in contribution, not position.
They remind us that fulfillment is not found in what we do, but in why we do it. The happiest professionals see their work as an extension of who they are, not a trade-off for who they wish to be.

Final Thoughts

If there’s one thread running through all this advice, it’s agency.
Careers are not linear—they are lived. The best professionals don’t wait for someone else to shape their path; they draw their own map.

So whether you’re at the beginning, middle, or twilight of your career, the message is timeless:
Move when it’s time.
Risk when it matters.
Seek those who lift you.
Invest in yourself.
Stay connected to people—and to purpose.

In the end, the best career isn’t the one others admire.
It’s the one you’re proud to have lived.

Check out my website for FREE resources and more at www.therivercoach.org
**NEW BOOK**  “Things We Desire” coming out 3 November 2025. Preorder at Amazon or any major book retailer.