Advice To Seniorpreneurs Seeking To Start A Retirement Side Hustle


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You’re either about to retire, just recently retired, or have been retired for some time when it strikes you out of the blue. It could be prompted by any number of factors. You could be worried about inflation eating away at your hard-earned savings. It could be you’re bored. Or it could be you miss the action, the challenge, and the lively banter with other people.

You’d like to get back into the business world, but you don’t want a boss. You want to work on your own terms, set your own hours and, in general, avoid the stress that you retired from. You want to start your own business, a small side hustle you can dabble in when you need a break from your leisure activities.

Believe it or not, doing this can do more than make you happy, it might just keep you healthy.

“Doctors say that people can age ten years in the first two years of retirement if they don’t have a purpose in their life,” says Victoria Tomlinson, Chief Executive at Next-Up in Harrogate, UK. “Starting a business means learning massively, mixing with younger people, getting into technology, and challenging yourself every day. In other words, you’ll have a purpose in abundance. And the feeling of satisfaction when you start seeing your idea take off—it’s like having children and the delights of watching them grow. I can’t think of anything better to do at this stage of life if you want to stay young and engaged.”

If you’re looking to start a “seniorpreneur” side hustle, you’re in luck. There’s no better time than today to find an easy way to supplement your retirement income.

“The growth of the gig economy and growing opportunities to work remotely have popularized having a so-called side hustle among Millennials and GenZs,” says Denis Litvinov, Co-Founder of FunCorp and CEO at Yepp, based in Limassol, Cyprus. “Retirees, however, can take advantage of the simple digital tools that are out there to earn extra income as well. The most low-risk opportunities are the ones that do not require any upfront investment.”

How can a beginner start a business?

Ah, but there’s one thing holding you back. You’ve never started a business. Doing so means taking a step into the unknown. And that can be scary.

But don’t let that hold you back. Others have done it countless times and in worse times.

“I started my business in 2008, during the housing crisis and subsequent recession,” says Julie Bee, President and Founder of BeeSmart Social Media and Lead From Anywhere in Charlotte, North Carolina. “I had lost my job, couldn’t get another one, and so I decided to take the risk and start a business. It was a rough few years, but once I focused in on the niche of social media, things took off.”

If you consider where you’ve been in your career, you’ll find nuggets you can use to help launch you into the perfect side hustle. Your own history shows you you’re less of a beginner than you think.

“Having T-shaped skills (where you have deep knowledge in one area but broad scope in others) in regards to corporate management gave me the confidence I needed to believe I could venture on my own as a solo founder,” says Kelly McDonald, CEO/Founder of Kyndoo in San Francisco. “In previous executive roles, at some point, I’ve managed all parts of a business that really span an entire corporation. My deep knowledge is in sales and revenue, so I was confident I could sell the product, and I’ve led operations, HR, and product teams in different organizations over the years. So, I felt that while it would be tough to go it alone, I at least had some idea of how the day-to-day roles worked and how I would move between them.”

Not only does the breadth of your experience give you a leg up, it also gives you insights you can only begin to imagine.

“As with most entrepreneurs, I saw a problem that needed a solution,” says Thyme Sullivan, Co-Founder & CEO of TOP the organic project in Duxbury, Massachusetts. “I had been an Executive in consumer products for 20+ years for PepsiCoPEP
, Coca-Cola and Nestle USA. I had seen consumer trends change over the years. Customers began to look for organic, non-GMO, gluten-free and sustainably sourced foods. The same happened with cleaning products, and then one day, my daughter started asking for organic lip gloss. Why wasn’t anyone talking about period products? When I went looking for period products for my daughter, I saw a category that had no transparency, little innovation and had been largely ignored; and the idea for TOP the organic project was born.”

What business should you start as a beginner?

Once you get over the idea that being a beginner won’t hold you back, it’s only a matter of determining which side hustle works best for you.

“There are a number of post-retirement entrepreneurial endeavors that have proven to be successful,” says Inez Stanway, CEO of Live Laugh Create in Atlanta. “For example, many retirees have found success as consultants, providing their expertise to businesses in need. Others have launched successful online businesses, selling products or services through web-based platforms. And still others have started brick-and-mortar businesses, using their experience and business acumen to tap into local markets. Whatever the approach, post-retirement entrepreneurship can be a great way for retirees to stay active and engaged in the workforce.”

What works for you? You’ll know it when you see it.

“If your idea consumes you, keeps you up at night, and all of your friends and family are sick of hearing about it, you’re probably at a good starting spot,” says Sam Harper, Co-Founder of Hippy Feet in Minneapolis. “From there, it’s not losing sight of what gave you that drive. It’s the grit to push through the failures and the self-honesty to recognize why they happened in the first place.”

Here’s an idea of some retirement side hustles you might consider.

How can you start a business with no money?

If the purpose of your side hustle is to give you a little extra spending cash, you probably don’t want to start a business that requires significant capital. In fact, you’d probably prefer to start a business that doesn’t cost any money. Or at least something you can set up before you officially retire. Mind you, don’t expect to earn a lot right off the bat.

“I started a website while working full time at my day job,” says Kristin Larsen, Founder of Believe In A Budget in Franklin, Tennessee. “I immediately treated it like a part-time job. Although I wasn’t making any income initially, I put in a lot of ‘sweat equity.’ After four months of working on my website in my spare time, it finally paid off, and I made my first $60. From there, everything started to snowball upward, and new doors started to open for me. My income grew, and I was able to leave my full-time job ten months after starting my website.”

How do you start a business from home?

Obviously, if you want to start a low-cost side hustle, you don’t want to rent an office. If anything, you want your office to be one of the spare rooms in your home. Thanks to the internet, this is extremely easy. Again, you can look at many examples of people doing this, regardless of their age.

“In my college dorm room, I wondered what would help me stand out in my application to Harvard Law School,” says Brian Robben, CEO of Robben Media in Cincinnati. “So I decided to start a blog. I grabbed the domain, bought a cheap WordPress theme, and started publishing three posts per week. Then I wanted people to see my blogs, so I dove deep into researching SEO and applying it to my site. The rest is history as my blog went on to receive millions of page views, and I used my skills to start a digital marketing agency.”

The best part about finding an internet delivery vehicle is that you can take a hobby of yours and find a way to make money with it.

“I started with a $400 Craigslist camera and my laptop from college,” says Casi Yost, Owner of Casi Yost Photography in Portland, Oregon. “I hustled and asked all of my friends and family if I could photograph them. They would refer me to other people and slowly, I started to build relationships, asked to shadow other photographers and built my website and business one step at a time. It has taken three years to finally have a workflow and system to track everything, but my business operates efficiently, and I don’t have to worry about leads coming in.”

Probably the best advice you can take if you’re interested in starting a retirement side hustle is to not overthink it and just do it.

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