Careers Aren't Linear: Lessons from Real Estate Developer Gregg Sandreuter

One of the biggest questions college students face is also one of the hardest to answer.

What do you want to do with your life?

For many students, the honest answer is simple: "I'm not sure yet."

That uncertainty was the focus of my recent conversation with Gregg Sandreuter, a commercial real estate developer and investor who has spent more than three decades building projects across the Raleigh-Durham area. Gregg is the Managing Partner of HM Partners and previously helped grow one of the region's leading development firms, Beacon Partners.

Despite a long and successful career, Gregg's story doesn't begin with a perfectly mapped-out plan. In fact, his path was anything but predictable.

Our conversation revealed several important lessons for anyone trying to figure out their next step.

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Most Careers Start Without a Clear Plan

Many students feel pressure to know exactly what they want to do early in life.

Gregg believes that expectation is unrealistic.

When he graduated from college, he didn't know he would end up in commercial real estate. He started his career in banking, went through a training program, and eventually realized that a large corporate environment wasn't the right fit for him.

That realization didn't happen overnight.

Instead, it came through experience.

Gregg described his career as a "bumpy path", which is actually how most careers unfold. Instead of a straight ladder, careers often look more like a series of stepping stones.

As he put it, sometimes you jump onto the first lily pad, then the next one, and eventually you find your direction.

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Hard Work Builds More Than Income

Long before he entered real estate, Gregg was already learning how business worked.

As a kid, he found creative ways to earn money. He delivered newspapers, cut grass, washed cars, and even sat in long gas lines during the 1970s fuel crisis so neighbors could buy gasoline.

Later, during college, Gregg started a painting business. He knocked on doors, hired friends, bought equipment, and worked long summer days painting houses.

The business paid his way through college.

But the biggest lesson wasn't the money.

It was the satisfaction that came from building something, delivering a service people valued, and developing a reputation for doing good work.

That early experience shaped how he approached business later in life.

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A Simple Decision Tool That Changed His Career

When Gregg was in business school, he still wasn't sure what industry he wanted to enter.

So he tried something unusual.

He used what he called the Ben Franklin method.

The exercise is simple:

1. Take a blank piece of paper.
2. Write the decision you are trying to make at the top.
3. Draw a line down the middle.
4. List the pros on one side and the cons on the other.

But Gregg took the exercise a step further. Instead of asking what job he wanted, he asked a different question:

What kind of life and work experience do I want?

On one side he listed things he wanted:

• Meeting lots of different people
• Being out in the world instead of stuck at a desk
• Creating something that would last beyond his lifetime
• Having the opportunity to build wealth
• Having independence in how he spent his time

On the other side he listed what he wanted to avoid:

• Being controlled inside a large bureaucracy
• Doing highly specialized work without broader exposure
• Being limited to a salary with no ownership
• Losing control of his career inside a large organization

When he looked at the list, one industry stood out.

Real estate.

It offered independence, entrepreneurship, and the ability to create physical projects that shape communities.

Soon after, Gregg accepted an opportunity to move to Raleigh and work in commercial real estate on a commission basis.

He is still here more than 30 years later.

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The Advice Gregg Gives Young People

When I asked Gregg what advice he would give college students who feel uncertain about their future, his answer was reassuring.

First, he said it's normal not to know.

In fact, it's expected.

Young people simply haven't had enough exposure yet to know what they enjoy doing.

Instead of worrying about having the perfect plan, Gregg encourages students to focus on three things.

1. Keep Improving Yourself

Develop skills.

Learn about the world.

Become the best version of yourself you can be.

This includes professional skills like technology and finance, but also personal qualities like kindness, integrity, and character.

2. Meet As Many People As Possible

Networking is one of the most powerful forces in a career.

According to Gregg, most opportunities come through people you know and relationships you build.

That means introducing yourself to alumni, asking questions, and being curious about other people's careers.

Sometimes a simple conversation can lead to an unexpected opportunity.

3. Be Willing to Work Hard

Gregg emphasized something that often gets overlooked today.

Simple habits matter.

• Show up on time.
• Stay late when necessary.
• Be willing to do whatever work needs to be done.

Even if it means sweeping the floor.

Those small actions build trust and reputation over time.

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Why Young People Should Worry Less

Perhaps the most comforting message Gregg shared was this:

Things tend to work out.

That doesn't mean life will be perfect or without setbacks. Everyone experiences failures and difficult moments.

But if you work hard, treat people well, and keep moving forward, opportunities tend to appear.

The future is not a single path.

It is a series of possibilities.

And often, the next opportunity comes from simply starting somewhere.

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Final Thought

At the end of our conversation, Gregg shared one more piece of advice for anyone who feels stuck or uncertain.

Start talking to people.

Ask them about their careers.

Ask what they learned.

Ask what they would do differently.

Those conversations might not give you all the answers immediately, but they can open doors you didn't know existed.

Sometimes the first step toward your future is simply a conversation.

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If you enjoyed this conversation and want to hear more insights from experienced leaders, you can listen to the full episode with Gregg Sandreuter on The Long Game podcast.