Retirees Must Have These Four Key Components To Make A Winning Side Hustle

Congratulations, you’ve made the decision to start your own business. Well, maybe “business” sounds a little too formal. Perhaps it’s only a small retirement side hustle. This, in itself, can benefit you in more ways than you think.

“Beyond financial rewards, there is a psychological benefit to having a venture to focus energy on,” says Charles Catania, Principal of Branding with Chuck in Vernon, Connecticut. “Whether it is in a consultancy capacity or beginning a woodworking business, for example, being able to create value is something in which many retirees see tremendous value. It is a great way to ease out of the workforce.”

Retirees from all walks of life have done this.

“Elizabeth Jackson was chief exec of Directorbank and now grows flowers for sustainable weddings (no air miles),” says Victoria Tomlinson, Chief Executive at Next-Up in Harrogate, UK. “Flowers from the Garden is brilliant, and Elizabeth says it keeps her fit. She loves gardening with her husband (he does the digging), and she gets enormous pleasure from happy brides.”

With these moderately sized gigs, it’s easier to keep them going when adversity strikes. In fact, given the modest expectations, retirees have an advantage when it comes to hard times.

“Turan Turan was a fireman and loved artisan foods,” says Tomlinson. “He started a cold-smoking cookery school and loved it. When Covid hit, he took it all online and continued to do well. He is passionate about what he does.”

You needn’t look at success as a roll of the dice or being in the right place at the right time. In fact, you can control your entrepreneurial destiny. All you need are these four fundamental “must haves” to make your side hustle a winning business.

Key Component #1: You need to be organized

Know where everything is.

This applies both to your thinking and to your management skills as well as to the system under which you operate your new business.

“With tremendous organization, determination, and the ability to keep the important thing the important thing, you can get pretty far on your own,” says Kelly McDonald, CEO/Founder of Kyndoo in San Francisco.

You can picture this as both the physical structure and your operating structure. Everything from pens, pencils, and ink toner has a specific place. If you work alone, your physical organization doesn’t have to be understood by others. Only you need to know where everything is.

From an execution standpoint, on the other hand, it’s best to have a written procedural manual. This way, when things get busy, you don’t have to remember how your business works. For the same reason, you want to make sure your implementation plan is well thought out and organized.

“Talk with advisors and colleagues who have started businesses before, and talk through what you’ll do next,” says Jeremy Babener, Founder of Structured Consulting in Portland, Oregon. “Then, implement for a month or two and revisit. If you’re organized, everything will go better. Today, many of the project management programs out there are incredibly useful on this front (e.g., Asana, ClickUp, JIRA). They allow you to make your plan, review it as a team, and then implement.”

Key Component #2: You need to have guts

Have no fear.

You’ve got to be brave enough to go against the current and to stand up against all those critics who complain about your going against the current. This requires a certain amount of intestinal fortitude.

“Every successful business comes from guts,” says Brian Coughlin, Founder & CEO of Hear It, LLC in Evanston, Illinois. “Starting a business is a risk, but you can mitigate that risk by doing your homework and preparing, so you have the best chance to succeed. You shouldn’t take blind risks, but you can’t play it safe either.”

People say entrepreneurs need the luck to succeed. That’s wrong. Without guts, that “luck” would not have been there.

“Entrepreneurs are survivors,” says Brian Robben, CEO of Robben Media in Cincinnati. “In my own community, we’ve seen restaurants and retailers who were hesitant to build websites and e-commerce stores before the Covid shutdown. During it, they became fearless in pursuing a digital transformation of their business by adding online components to generate cash flow that they most likely didn’t fully understand. Their willingness to serve customers and provide food for their employees and family was remarkable, even during a crisis where it would be forgiven if they became selfish.”

Key Component #3: You need to be persistent

Never give up, never surrender.

Since when does everything always go as planned? Spoiler Alert: It never does. There’s even a saying for this: “Into each life, a little rain must fall.”

And when those rain clouds do appear, what do successful entrepreneurs do? They don’t pack up their gear and head for shelter. No, they plant their feet firmly into the (muddy) ground and start selling umbrellas.

“When you study success and read extensively about entrepreneurs, you realize that successful people come from a variety of backgrounds and circumstances, but they have one thing in common—they consistently do the work,” says Case Lane, Founder of Ready Entrepreneur in Los Angeles. “The only talent needed is knowing you can make that commitment to keep working to ensure business success.”

Entrepreneurs don’t fear change (see above); they see it as an opportunity.

“I knew how to solve a problem that many people were experiencing, and I knew I could help those people,” says Chane Steiner, CEO of Crediful in Scottsdale, Arizona. “I certainly believed I could take that offer and turn it into a business, but mostly I figured out the rest as I went along. Identifying existing problems is a big skill to develop, and finding solutions is largely a matter of never giving up.”

Do you wonder if you have what it takes to “never give up”? Don’t worry. No one does until they face that challenge in real time.

“Nobody knows whether they ‘have it’ to succeed before starting out, and success is not driven primarily by talent,” says Florian Bohn, CEO and Founder of GuRu, Pasadena, California. “Success is the result of persistence. Persistence means keeping ‘at it’ even in the face of unlucky turns—over time, we will have “undeserved” bad luck, but also, let’s be honest, undeserved good luck. Over time, the element of luck or chance (to use a more accurate and neutral term) disappears, and what is left is one’s persistence.”

Key Component #4: You need discipline

Keep your head, stay rational—“Stay calm and pass the ammunition.”

It’s one thing to say you’re organized, to show you have guts and to demonstrate a little persistence, but it’s another thing to do it. Discipline comes into play because you’ve got to demonstrate these three characteristics 24/7. This plays out in the mind and in the heart, and you’ll be wise to get help from any source you can muster.

“I needed spiritual focus number one,” says Sabriya Dobbins, Founder of Project Passport LLC in Raleigh, North Carolina. “I read many books on spiritually led entrepreneurship, understanding how to leave the scarcity mindset, and getting stuff done. I needed some money, of course, too, but having a bit saved up was what I needed as I created a model with as little overhead as possible. I needed the guts to shut up and do it. I was a very insecure girl with severe anxiety; therefore, in that dirty, old apartment in Belize, I had to choose. What girl was I now, and who did I want to be? I chose to work towards the future self.”

People who don’t appreciate what this means will complain of “the daily grind,” “being in a rut,” or mindlessly doing the same things repeatedly. It may sound cliché, but a successful business is like a well-oiled machine. It faithfully performs the same tasks ad infinitum in a reliable and predictable fashion.

“I am an old football player in college and high school,” says Darrell Andrews, Workforce Development Consultant/Career-Life Coach at Darrell Andrews Enterprises in Bear, Delaware. “On the field, you have to be confident, a risk-taker, intelligent, ward off your opponent, and knowledgeable of a playbook. As a business owner, it is no different. I possess all of these traits not because of sports but because I like to succeed at what I am committed to.”

Across all businesses and industries, including people of all types of backgrounds, these four fundamental factors describe what it takes to create a successful business.

The good news? You can train yourself to learn and practice all of them.