Why 35 Is the Golden Age for Blossoming into an Entrepreneur

5 Advantages You Have Over Twenty-Somethings

Something happens to a man at 35. I know because it happened to me, and it is still happening to men at that age. As an angel investor for almost 25 years, I continue to observe it. (I’m not sure about women. I can only speak as a man. If you’re a woman, I’d especially love to hear your thoughts on this.)

The Restlessness Begins

He knows there is something greater to be accomplished. What he is doing now isn’t enough. Sure, the money is good and so is the title. But there is this feeling in his gut.

There is more, a lot more. Now is the time. He is ready to do something significant. It is time to step out and start something or join a startup.

My most successful investments were first time entrepreneurs between the ages of 35 and 38. This wasn’t part of my investor profile when I got started, but it is now.

My Unrest Begins

I was making great money as the COO of a UK-based public professional services company. I ran their US operation. They were a great company. They liked me and what I was doing. They gave me lots of freedom and provided a lot of upside opportunity. But I was unhappy.

One Saturday morning, my then five-year-old son and I went for a haircut. While he was sitting in the barber chair, I decided to take a walk around the strip center.

Right next door to the barber shop was a knick-knack shop. I’m not the ideal customer profile for one of those shops, but hey, I was killing time.

Sign from a Knick-Knack Shop

I walked in, and I saw this sign. It was white with blue script. It said, “Bloom where you are planted.” I read it, and it stopped me for a moment. I eventually walked on and looked at the rest of the stuff on display. But I came back to the sign and eventually bought it.

The sign contained the message I didn’t want to hear but needed badly. I knew I was sitting on a fat opportunity, but I wanted out. I also knew thinking this way was nuts. I was thirty-five years old. Married to Kathy for twelve years. We had three kids, all under twelve. As the provider of our family, I faced cars, house, and tuition.

Stay, You Idiot!

“Stay where you are!” my inner voice kept screaming to me. But my heart was elsewhere. I did hang the sign on the wall directly opposite my desk chair. Every time I looked up or had a meeting with someone, I would look past them and see the advice, “Bloom where you are planted.”

The sign helped for three years…not really. The truth is, the sign was really a reminder to move on. There it was, “Bloom where you are planted…not.” I just didn’t have the courage to move on. But my boss did.

I’m Outta Here!

He said to me over breakfast, “If you don’t enjoy doing what you are doing, leave and do something else.” I agreed right there over bacon and eggs. I’m out of here! That was the beginning of a scary but exciting journey. I was off to find my next new thing. Back to the Atlanta startup community I went. Who knew I would become an angel investor?

That’s my story at 35 years old. I continue to hear the same story from would-be entrepreneurs in very similar situations. They don’t tell me about the sign. But they do have the “Bloom where you are planted” message playing in their head. And their heart is screaming, “No. There really is something bigger and better and more fulfilling out there for you.”

Let Your Heart Lead

My advice is: Follow your heart. If you don’t, it will eventually die. Don’t be that guy.

Consider this. You have five assets twenty-somethings don’t have:

  1. You are an expert at something. You can prove it because you made a living at it. Enough to support your family.
  2. You have experience. You’ve been there and done that, including leadership and management.
  3. You are settled and dependable. A family makes for a very committed entrepreneur.
  4. You have wisdom. Wisdom comes from experience. And experience comes from lack of wisdom.
  5. You have network. Your network includes fellow employees, your clients, and your vendors. You know a lot of people, and they are all impressed with you.

Think of what you can do. Look up. The opportunities are right in front of you. Replant, then bloom again. Just bloom!

Please note: I reserve the right to delete comments that are offensive or off-topic.

4 thoughts on “Why 35 Is the Golden Age for Blossoming into an Entrepreneur

  1. Turning 35 on 14 Sept.

    This is pretty scary for how spot on this is for me…
    Ironically, I see billboards, t-shirts, ‘social media’, & other signs that say the opposite of the one you saw, in that they dare me to make that jump.

    *I just keep going back to the mortgage, tuition (daycare) and family that needs steady income.


    • Ritchie this entrepreneuring is not for everyone. The timing, finances, idea and passion must all align. If not, bloom where you are planted!

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