During my first year of self-employment I earned $13,000. I lived on ramen noodles and peanut butter and turned down social outings because I couldn’t afford a glass of wine. It was one of the best years of my life.

Thirteen years later, my agency employs 31 people who assist baby boomers with their Medicare insurance decisions in 47 states. I often look back fondly at that first year, reminiscing about how it felt to be scared and broke and hopeful all at the same time.

And I wonder… why didn’t I try it sooner?

Mostly, it was fear of failure. I thought I’d be good in insurance sales, but what if I was wrong? So, for years I waited and dreamed about leaving my career in temporary staffing, where I was overpaid but also overworked.

Finally, after watching a friend leave her job and strike out on her own, it dawned on me that I was wasting time. I thought to myself, “I think I can do this, so I will.”

How about you? Have you been dreaming of working for yourself for ages?

Well, you can. Even in your 60s or 70s.

My career as a Medicare insurance broker has given me some interesting insight into the financials of baby boomers. Many continue working for an employer well past 65 not because they want to, but because putting kids through college didn’t leave much for their own retirement.

However, working for someone else isn’t their only option anymore.

Forbes reported that 18% of workers over 65 are self-employed, making this one of the fastest growing groups of business owners. So, if you aren’t quite ready to hang up your work spurs, now might be your chance to transition into working for yourself.

Here are some of my tips for making the leap from employee to employer so you can live the retirement of your dreams:

Ditch the Self-Doubt

Self-doubt is often the biggest hurdle standing in our way. We sabotage ourselves with thoughts that no one will want what we have to offer, or that too many other people are already doing what we want to do.

Remind yourself that you are the only person who can share your specific knowledge, wisdom, art or life experiences. You might be surprised at how interested the world is in what you have to offer.

Start with Something You Love (Even if Others Don’t)

In childhood, not many people think that they want to be an insurance agent when they grow up. Unless their family is in the business, it’s not a career that seems even remotely glamorous. Yet oddly enough, I love what I do, and I knew back in 2004 that I would.

Working for yourself is sometimes less about the industry and more about the challenge: the challenge of making your own way; the challenge of building something good; the challenge of making life easier for someone else.

It’s about finding that warm, fuzzy, ‘here’s why I do this’ reason that gets you up out of bed every day. Choose something you enjoy that will also challenge you. This will carry you a long way, and the rest will often fall into place.

Vanquish the Vague

Defining your niche is critical. For example, if you go into real estate and sell every type of property on the planet, your skill and knowledge can get diluted and spread too thin. Choose one and put 1000% of your effort into owning that niche.

In the entrepreneurial world, we call this ‘niching down.’ You’ve heard the expression “the jack of all trades is the master of none.” When it comes to business, it’s true.

You Don’t Have to Know Everything Up Front

Perfectionism is the enemy of new business owners. You don’t have to be the Bill Gates of whatever industry you decide to go into. It’s more important that you are committed to the process and willing to learn as you go.

Consider Starting with Your Old Employer

When I left my staffing job, I negotiated a part-time contract with my former employer. We struck a deal that would give me enough income that I wouldn’t starve on my first-year insurance earnings, and it helped my former employer because I stuck around long enough to train my replacement.

Is there something you can offer your employer in exchange for part-time hours while you build your business?

Stop Focusing on Your Age

Many baby boomers perceive age to be a negative factor when it comes to business. I beg to differ. I employ several women in their 60s, and they are some of the best employees we’ve ever had. There are industries out there who are in a downright panic over losing their boomer workforce.

Besides, by working for yourself, you’ll never have to worry that an employer won’t hire you over a few gray hairs.

The insurance industry is a great example of an ageless opportunity. Real estate is another. There are scores of uber-successful female agents in their 60s who have zero plans of slowing down anytime soon.

Helping Others Is Its Own Reward

Many people like the idea of starting a business but aren’t sure exactly what they would enjoy doing. When all else fails, choose something where you can help others.

Things that come to mind are teaching, writing, pet-sitting, virtual assisting, coaching, cooking or tutoring. Any service that helps our fellow humans is sure to be fulfilling, and having a full heart is what all of us are really after in the end.

Have you got an idea for a great business, or have you already started working for yourself? How did you decide on it? What do you love about it? We’d love to hear your thoughts in the comments below.

Let's Have a Conversation!