How to Go Confidently into Entrepreneurship in Midlife

First, a little rant: Have you ever tried to find an image of a ‘confident entrepreneur’?

I just did, and I got a bunch of twenty-somethings with six-pack abs stepping out of Lamborghinis, carrying shopping bags, and wearing very red lipstick.

I can’t relate.

So I changed my search to ‘middle-aged’ entrepreneur, and I got thirty-somethings with six-pack abs stepping out of Lamborghinis, carrying shopping bags, and wearing very red lipstick.

Who are these people?

If you just stepped out of a Lamborghini with your arms full of shopping bags, this post is not for you.

Rant over. Here we go:

After 20 years of bouncing business ideas around in my head, I became an entrepreneur at age 46.

I was a single mom of two with a solid government job and the potential for a pension if I could last another 19 years in my office.

I had a corner office with two windows. The work was relatively easy, and my boss was nice.

But I was bored out of my mind.

So, I hatched a plan to escape, and here’s how it unfolded:

Step One: I Saved Up a Financial Cushion

I’ve always been a saver, so by the time I decided to leap, I already had most of what I needed saved up. I wanted enough money in short-term savings to cover at least a year’s expenses, just in case.

A year would give me enough time to determine whether or not my business would make it, and to find new employment if my plan failed. With two kids depending on me, I couldn’t afford not to have money saved up before I switched to self-employment.

A financial cushion gave me the confidence to weather ups and downs in my business without worrying about my bank balance every day.

Step Two: I Started Before I Stopped

I started working on my new business on the side months before I resigned from my full-time job. Even though the long hours were tiring, I was energized by the idea of change.

I worked from sunup to well past sundown almost every day for almost two years before I let go of my full-time job. At that point, I felt confident I had enough business to make a go of it.

Anyone who tells you that building a business is easy is either incredibly lucky or lying to you. It’s work.

Building the base of my business before I left my job gave me the confidence to move forward without stepping off into a void.

Step Three: I Used My Network

I went out on my own in the same field I had been working in for years, so I had lots of experience to draw from. And I had a network of people who wanted to help me grow my business.

But they weren’t even aware that I had started a business, and they couldn’t help me grow unless I asked.

I used my network and my experience to my advantage.

I talked about my new venture with everybody I knew.

Step Four: I Learned Continually

New trends, technologies, and best practices emerge all the time. I can’t make the mistake of resting on my laurels just because my business exists.

A caveat: there is such a thing as too much learning. Some people take course after course after course before they take action. That’s not what I’m talking about.

I’m talking about seeking out specific skills you know you need, learning those skills, and implementing them immediately.

The most successful people have very little gap between the time they learn something new and the time they implement that new learning.

Step Five: I Followed the Signals

We’ve all heard the phrase, “Lean in,” meaning we shouldn’t let fear hold us back. We should learn from our mistakes and use them to make us stronger. I think that’s true.

But I think “Follow the Signals” is better advice.

Follow the Signals means to follow your success and double down on it.

For example, I opened my business as a private practice dietitian. I rented an office and credentialed with insurance companies. Everything was great!

And within a couple of months, the pandemic broke out.

We didn’t know whether insurance would cover telehealth services, and people were scared to come to the office.

I had to pivot, so I started writing for healthcare companies. Pretty soon, my writing income exceeded my nutrition counseling income.

So, I followed the signals and doubled down on the writing. Today, I’m still writing for healthcare companies. Plus, I’ve self-published an Amazon best-seller, and I coach newer writers to start and scale their writing businesses.

That never would have happened if I hadn’t followed the signal of writing success.

It’s Now or Never

If you’re like me and you get to mid-life and haven’t done the thing you’ve always wanted to do, there’s a sense that time is running out.

I didn’t want to look back and wonder, “What if?”

And the truth is, it’s been harder than I ever thought it might be. And it’s been so much fun at the same time.

I’m not stepping out of a Lambo with my arms full of shopping bags. Yet.

But I wake up at 4:30 a.m. every day with my business on my mind because I’m excited about what I want to do. And I wouldn’t trade that feeling for anything.