Where Do You See Yourself in 10 Years?

Piggybacking off my “What Is a Mentor, Really?” column, I ran into one of my biggest mentors at the post office recently. When we first met, I was fresh out of college in my first “real” job — marketing for a health system. He was the CEO. Fifteen years later, he’s still one of the most influential mentors in my life.

We hadn’t talked in years, but I’ve always gone back to the lessons he taught me in that first job. When we caught up, I shared how our business has grown and asked if he’d be willing to help me think through what’s next. He agreed. And the very first thing he asked me, the first time we’d sat down in over a decade, has been echoing in my head ever since:

“Where do you want to be in 10 years?”

Simple question, right? I don’t think so. Most days, I’m just trying to make it to tomorrow. Ten years can feel like a lifetime away.

Then, this past weekend, perspective hit hard. My grandfather, another huge mentor in my life, entered hospice. As I sat with him, watching him sleep, I thought about the life he’s lived and the impact he’s had. He doesn’t have 10 years to set goals and reverse-engineer them. He has days. My prayer is that he feels at peace with the life he built.

None of us knows how much time we have. But while we’re here, it’s on us to define our end goal. That’s the first step to building a life and business we actually want.

If you’re trying to answer the “10-year” question, here’s the thought process I’m using. Maybe it will help you, too.

Define Your Version of Success

What does success look like to you? Is it financial freedom? The number of people you help? The size or longevity of the business? What you can pass down to your family?

It’s easy to get swept up in social media and start chasing someone else’s finish line. That’s their journey, not yours. Be honest: do you actually want that, or do you feel like you’re supposed to want it? Live your truth. Name what would genuinely make you feel successful.

Get Real About Today

Every business needs a visionary. Visionaries dream big and sometimes lose touch with the starting line. Take a clear-eyed look at your current reality so you can build a realistic ten-year strategy.

• Financials: Where are your margins, pricing, and cash flow today? If you’re at $1M in revenue now and want to be at $100M in 10 years, that’s not a casual “we’ll see.” It will take aggressive growth, capital, leadership, and discipline.
• People: Do you have, or can you develop, the leaders who will carry this with you: operations, finance, sales, service?
• Systems: Are your processes documented? Do you run the business by numbers, or by feel?
• Self: Are you doing the work to become the person who can lead at the next level?

Decide Who You’re Becoming

Life isn’t just P&Ls and truck counts. Who do you want to be 10 years from now?

Do you imagine more freedom with your time? Beach trips with a drink in your hand? Front row at every PTA meeting? Becoming a stronger leader? Building a massive company? Your personal picture drives your business plan more than you think.

When my mentor asked me the question, the first image in my mind wasn’t a revenue target or a multi-branch map. It was my daughter: her growth and me being present for it. That surprised me. I’ve always been very career-focused. My career still matters deeply, but the very first thing I saw was her, not a spreadsheet. That told me a lot about what my next 10 years should look like.

So, ask yourself: What’s the first thing that comes to mind when you picture your life 10 years from now? Pay attention to that.

Reverse-Engineer It and Keep Refining

Now put it on paper.

• Write the vision. Describe your 10 year life and business in clear language;
• Build milestones backward. If this is Year 10, what must be true by Year 7? Year 5? Year 3? Year 1?
• Talk to your people. Share the vision with your family and your core team. Ask for their support and input;
• Create guardrails. Set a simple scorecard and a monthly cadence to review progress, adjust, and keep moving; and
• Be flexible. Life changes. Markets change. You’re allowed to tweak the destination and the route.

You’ll be amazed how your perspective shifts when the path is visible and shared.

Here’s my encouragement to you: you will wake up in 10 years no matter what. The question is whether you’ll wake up in a life and business you meant to build or one you built by accident.

Start with the end. Define success for you. Get clear about where you are today. Decide who you’re becoming. Then reverse engineer your way back to this week, this month, this year.

That’s how we move from “just trying to make it to tomorrow” to building the tomorrow we actually want.