What I Wish I'd Known at 20 (That Nobody Bothered to Tell Me)

If I could go back and have a conversation with my 20-year-old self, it would be a short conversation. Not because there isn't much to say, but because he wouldn't listen to most of it.

At 20, I thought I knew how life worked. I thought success came from following the rules, working hard, and waiting for opportunities to find me. I thought the smartest people made the fewest mistakes.

I was wrong about everything.

Twenty-five years, multiple businesses, countless failures and a few successes later, here's what I wish someone had told me. Not the motivational stuff—the practical, uncomfortable truths that would have saved me years of trial and error.

Lesson 1: Your Biggest Strengths Will Become Your Biggest Weaknesses

At 20, I was proud of my ability to analyze situations thoroughly before making decisions. This trait helped me excel in school and early jobs. It made me feel smart and prepared.

By 30, this same strength had become my greatest weakness. I was so good at finding potential problems that I talked myself out of taking risks that could have changed my life. My thoroughness became paralysis.

Every strength taken too far becomes a liability. Your attention to detail can become perfectionism. Your caution can become cowardice. Your independence can become isolation. Watch for this pattern in yourself, and if you're already seeing it, read about overcoming analysis paralysis before it costs you opportunities.

Lesson 2: Nobody Knows What They're Doing (Including Successful People)

I spent my twenties waiting to feel ready before pursuing bigger opportunities. I assumed successful people had figured something out that I hadn't yet learned.

Then I started working with millionaires and executives and discovered something shocking: they're all making it up as they go along. The difference isn't that they know more—it's that they're comfortable acting despite not knowing everything.

The CEO who hired me for a million-dollar project admitted halfway through: "I have no idea if this strategy will work, but it's the best option we can see right now." The entrepreneur who sold his company for $50 million told me: "Most of our success came from lucky accidents we hadn't planned for."

Stop waiting to feel competent before taking action. Competence comes from acting despite feeling incompetent. If you need help taking action while feeling unprepared, start with small actions that build confidence.

Lesson 3: Your Timeline Is Completely Wrong

At 20, I had my entire life mapped out: graduate by 22, promoted by 25, management by 30, wealthy by 40. I thought success was a linear progression that happened on a predictable timeline.

Real life doesn't work that way. The most important opportunities come at unexpected times. The biggest breakthroughs happen after what feels like years of going nowhere. Success comes in waves, not steady increments.

I made my first million at 35, lost it at 38, made it back at 42. Nothing happened when I thought it would. Everything took longer than expected, except the parts that happened faster than I could process.

Stop holding yourself to arbitrary timelines. Focus on consistent action and let the results come when they come. Impatience will make you quit right before the breakthrough happens.

Lesson 4: Your Network Matters More Than Your Knowledge

I spent my twenties accumulating credentials and skills, thinking that competence alone would create opportunities. I was wrong. The opportunities came from relationships, not résumés.

Every significant business opportunity I've had came through someone I knew, not something I applied for. Every major contract came from a referral, not a cold pitch. Every meaningful partnership started with a conversation, not a proposal.

But here's the part they don't tell you about networking: it's not about collecting contacts—it's about providing value before you need anything. The people who helped me most were people I had helped first, usually without expecting anything in return.

Lesson 5: Most Advice Is Wrong for You

Business books, success podcasts, motivational speakers—I consumed it all. I thought if I learned enough strategies and frameworks, success would be inevitable.

What I discovered is that most advice is autobiographical. It worked for the person giving it because it matched their personality, their circumstances, their strengths, and their market timing. That doesn't mean it will work for you.

The most expensive mistakes I made came from following advice that was perfectly good for someone else but completely wrong for my situation. I tried to force myself into other people's success formulas instead of developing my own.

Learn principles, not tactics. Understand why something works, not just how it works. Then adapt it to your unique situation. If you're tired of following advice that doesn't fit your reality, read about why most entrepreneur advice comes from the wrong people.

Lesson 6: Failure Is the Best Education Money Can't Buy

I was terrified of making mistakes because I thought they reflected poorly on my intelligence. I avoided risks that could make me look foolish or unprepared.

This turned out to be incredibly expensive. Every opportunity I avoided to preserve my image was an opportunity someone else took to gain experience. While I was protecting my reputation, they were building their capabilities.

The business breakthroughs I eventually had didn't come from avoiding failure—they came from failing faster and learning from it more systematically than my competitors. This is why failing actually increases your chance of success.

Lesson 7: Action Beats Intelligence Every Time

In school, being smart meant having the right answers. In business, being smart means taking action with incomplete information and adapting as you learn.

I watched "less intelligent" people build successful businesses while "smarter" people got stuck in planning phases that never ended. The difference wasn't IQ—it was willingness to act before feeling ready.

Your intelligence is an asset, but only if you combine it with action. Smart people who don't act stay smart people who don't achieve much. Average people who act consistently often outperform genius-level people who only act when they feel certain. Learn how to turn small actions into big results.

Lesson 8: Money Follows Value, Not Effort

I thought working harder automatically meant earning more. I believed that effort always translated to results. I was wrong about both.

Money doesn't follow effort—it follows value creation. You can work 80 hours a week on something nobody wants and earn nothing. Or you can spend 10 hours a week solving a problem people desperately need solved and earn more than you ever imagined.

Focus on understanding what people actually need, not on working harder to give them what you think they should want.

What I'd Tell My 20-Year-Old Self (And What I'm Telling You)

If I could have that conversation with my younger self, here's what I'd say:

Start before you feel ready. Take risks while you're young enough to recover from them quickly. Build your failure tolerance while the stakes are still relatively low.

Your strengths will become weaknesses if you don't manage them consciously. Your perfectionism will become paralysis. Your caution will become cowardice. Your independence will become isolation.

Nobody knows what they're doing, including the people who look like they have it all figured out. This is liberating—you don't need to wait until you know everything to start something meaningful.

Success doesn't happen on your timeline. It happens when it happens. Focus on consistent action and let the results surprise you.

Most importantly: your worth isn't determined by your achievements. You're valuable whether your first business succeeds or fails, whether you make your first million at 25 or 45, whether you follow conventional paths or create your own.

Your Life Lessons Action Plan

Today: Identify one area where your biggest strength might be becoming a weakness. Are you analyzing when you should be acting?

This week: Take one action you've been avoiding because you don't feel ready. Prove to yourself that you can handle acting despite uncertainty.

This month: Stop following advice that doesn't match your situation. Start experimenting to discover what actually works for you.

The biggest lesson I learned is that life doesn't wait for you to feel ready. Opportunities don't pause while you get comfortable. Success doesn't happen on your preferred timeline.

If you're tired of waiting for the perfect moment and ready to start building proof that you can handle uncertainty, the First Step Entrepreneur program gives you structured practice taking action despite fear. You'll learn these lessons through experience instead of having to wait 25 years like I did.

Remember, the lessons that matter most can't be taught—they have to be experienced. But you can choose to experience them through small, manageable risks instead of waiting for life to force bigger lessons on you. If you're dealing with career change anxiety about making these changes, you're not alone.

I can't give you back the years I spent waiting to feel ready. But I can give you permission to start before you feel prepared, to act despite uncertainty, and to build the business and life you want instead of waiting for perfect conditions.

Your 20-year-old self made the best decisions they could with the information they had. Your current self can make better decisions with better information. Start now.