At 25, I had a plan. Engineering degree completed. Consulting career launched. Five-year trajectory mapped on a spreadsheet that I reviewed every quarter. The plan was clean, logical, and entirely wrong about what the next eighteen years would actually look like.
I’m not writing this to argue against planning. Plans are useful. But the things that actually built my career — the accidental programme managership, the hotel room card tricks, the pandemic pivot, the kitchen-table product company — weren’t on any plan. They were the result of skills, habits, and perspectives that I wish someone had told me to develop at 25 instead of at 35.
Here’s what I wish I’d known.
Skills Compound. Titles Don’t.
At 25, I was focused on the next title. Junior consultant. Consultant. Senior consultant. The title conveyed status, and status felt like progress.
Eighteen years later, nobody cares what my title was in 2008. What they care about — what has actually produced career value — is what I can do. The skills compound because each one builds on the previous ones. Strategy analysis enables systems thinking. Systems thinking enables product development. Product development enables entrepreneurship. Each skill layer makes the next layer accessible.
Titles reset when you change companies, industries, or career paths. Skills transfer everywhere. The consulting skills I built in my twenties transferred directly to building Vulpine. The product development skills from Vulpine transferred to writing and teaching. The teaching skills are transferring to whatever comes next.
Invest in skills. Let the titles take care of themselves.
Learn to Sell Before You Need To
I was allergic to sales at 25. By 40, I’d realized that selling is the multiplier for every other skill. Technical excellence without sales ability is a tree falling in an empty forest.
The earlier you develop comfort with selling — not manipulation, but the ability to communicate value and ask for commitment — the more productive every other skill becomes. An engineer who can sell is more valuable than an engineer who can’t. A writer who can sell is more published than a writer who can’t. A founder who can sell survives longer than a founder who can’t.
Don’t wait until you start a business to learn sales. Learn it in your current job. Sell your ideas to colleagues. Sell your proposals to management. Sell your expertise to clients. Every professional interaction is practice.
Build Your Network Through Usefulness, Not Events
At 25, I thought networking meant attending events and collecting business cards. By 35, I’d learned that the only connections that matter are the ones built through genuine usefulness.
Be the person who makes the introduction. Share the resource. Answer the question. Help the colleague. Each act of usefulness creates a connection that is qualitatively different from a handshake at a mixer. The useful connections produce opportunities. The event connections produce LinkedIn notifications.
Start being useful now. The network you build through usefulness at 25 will produce more career value by 35 than any credential.
Your Body Is Infrastructure
At 25, my body was an afterthought. I could skip sleep, eat garbage, and skip exercise without visible consequences. The consequences weren’t visible — they were deferred.
By 40, the deferred consequences arrived: lower energy, slower recovery, diminished cognitive performance, and the realization that your body is the infrastructure your entire career runs on.
Build the habits at 25. Sleep seven hours. Walk daily. Eat real food. These habits, formed when forming them is easy, become the infrastructure that supports everything you build at 35 and 40.
Start Building Something Before You Feel Ready
At 25, I had ideas. At 40, I had a business. The fifteen-year gap between ideas and execution is the most expensive period of my career — not in money lost, but in learning deferred.
Every year you spend planning instead of building is a year of compounding experience you won’t get back. The product you launch today and fail with tomorrow teaches more than the plan you refine for a year and never execute.
You have permission to start small. One product. One customer. One transaction. The compound clock starts when you start, not when you’re ready.
Find a Mentor Who Tells You the Truth
At 25, I surrounded myself with people who agreed with me. It felt supportive. It was comfortable. It was also an echo chamber that reinforced my assumptions instead of testing them.
The mentor who told me I was wrong changed my career more than any supporter ever did. His blunt feedback prevented financial mistakes and strategic errors that would have cost years to recover from.
Find someone who has built what you want to build and ask them for honest feedback. Not encouragement. Feedback. The discomfort of hearing the truth is a small price compared to the cost of acting on comfortable lies.
The 5-Year Perspective
Most of what stressed me at 25 is invisible at 43. The project deadline that felt catastrophic. The client who seemed unreasonable. The promotion I didn’t get. The competitor who seemed unstoppable.
Five years from now, most of what stresses you today won’t matter. The things that will matter — your skills, your relationships, your health, your character — are the things that compound slowly and invisibly. Invest in them, even when the urgent things are louder.
Embrace Being Wrong
At 25, being wrong felt like failure. I defended positions past the point of reason because admitting I was wrong meant admitting I didn’t have it figured out, and having it figured out was my identity.
At 43, being wrong is data. The mentor who told me I was wrong prevented a catastrophic strategic error. The five business failures each produced a framework more valuable than the money they cost. The product that shipped too late because I was wrong about timing produced the Ship It Ugly principle that now anchors everything I teach.
Being wrong quickly is cheaper than being wrong slowly. The founder who launches a product and discovers the market doesn’t want it loses weeks. The founder who researches for a year and then discovers the market doesn’t want it loses a year. Both were wrong. One was wrong faster.
Develop the habit of saying “I was wrong about this. Here’s what I learned.” Say it to your team. Say it to your partner. Say it to yourself. The habit strips the ego from the process and converts every mistake into information. Information compounds. Ego doesn’t.
The Thing Nobody Tells You About Success
At 25, I thought success was a destination — the point at which the work pays off and the struggle ends. At 43, I know that success creates its own problems: identity fusion, lifestyle inflation, the pressure of expectations, and the disorientation that follows achieving the thing you’ve been working toward.
Every level of success introduces a new set of challenges that the previous level didn’t prepare you for. The founder who struggles to get ten customers faces different problems than the founder who has 10,000 customers. The problems evolve. The work evolves. The person has to evolve too.
Build the infrastructure for handling success before you need it. The weekly review. The accountability partner. The physical habits. The relationships that tell you the truth. These aren’t just tools for the hard times. They’re the systems that keep you grounded when the good times arrive and try to pull you off course.
The Winding Road
My career didn’t follow the spreadsheet. It followed a winding path through consulting, engineering, innovation labs, accelerators, product companies, four countries, a company exit, and a reinvention at 40.
Each turn made sense only in retrospect. At the time, each felt like a deviation from the plan. The deviation was the career.
If I could tell my 25-year-old self one thing, it wouldn’t be a specific piece of advice. It would be this: the plan is a starting point, not a destination. The skills, the relationships, the health, the willingness to build before you’re ready — these are the constants. Everything else is a variable.
Build the constants. Let the variables surprise you. The winding road is the career.
