Each year around this time, as college graduation season rolls around, I’m reminded of one of the questions I ask most often on the Outside Insights podcast: “What advice would you give your 21-year-old self?”
That early post-college chapter, full of odd jobs, uncertainty, and big questions, felt like a turning point in my own life. It marked the start of what I hoped would be my first “real” career move.
In the spirit of that question, I’ve been reflecting on the themes I hear again and again from my guests: people who’ve faced adversity, bridged the gap between where they were and where and where they wanted to be, and made a lasting impact through leadership, business, or service.
Here’s what I (and many of my guests) wish we knew earlier:
1. Practice Grace, with yourself and with others:
Don’t be so uptight. Life doesn’t go according to plan, and that’s okay. The moments you think are make or break are often just small stepping stones along your path. Give yourself permission to grow, to learn, and yes, to fail.
“Be patient toward all that is unsolved in your heart and try to love the questions themselves.” – Rainer Maria Rilke
2. Stop comparing paths:
Everyone’s journey looks different. Many leaders regret not charting their own course earlier, often held back by expectations from family or society. You don’t have to be a lawyer or a doctor to be successful. You can define what success means for you. If your dream is to open a coffee shop – open the coffee shop! Your path is yours alone to walk – and the people that really matter will stick around to walk it with you.
3. Appreciate the process:
Your early career choices, where you live, who you work for, who you choose to spend time with, shape you more than you’ll realize at the time. Try to enjoy the process instead of rushing through it.
As Pink Floyd famously put it:
“And you are young and life is long, and there is time to kill today… And then one day you find ten years have got behind you.”
4. Just start:
Perfection is a myth. Life is messy. Jobs won’t always be fulfilling. Relationships won’t always make sense. But every moment teaches you something valuable. Start now and sort it out along the way.
5. Know yourself:
I wish I had spent more time understanding my values, instead of adopting other people’s vision and goals. I was following someone else’s version of success, and I didn’t even realize it until many years had passed.
A mentor once helped me ask the right questions: Who am I? What matters to me? What kind of life do I want to build? Those questions changed everything.
6. Take the risk before life piles on:
Travel. Try a hobby. Walk the PCT. Start the business. Say yes before “real life” fills your calendar. If you wait for the perfect moment, it may never come.
Ready to Reflect? Block out 30 minutes and ask yourself: What advice would I give my younger self?
You might be surprised at what comes up. It’s a powerful exercise that can clarify who you are today, and who you still want to become.
If you’re ready to take the next step, here are three ways to dig even deeper:
- Join the Life Plan Review group – A 10-week experience helping people build their earned life with structure, support, and accountability.
- Download the free Life Tree Activity Journal – A guided tool to help you close the gap between where you are and where you want to be.
- Subscribe to Outside Insights on Substack – Weekly reflections on leadership, life, and building a meaningful career.
And if this message resonated with you, forward it to a friend or colleague who could use it, too.
Let’s keep learning, at every stage of the journey.
Until next time, friends,
Chris