In 2006, Congress established National Entrepreneurship Week. It is celebrated roughly the third week of February. You might think of “entrepreneurship” in terms of new business start-ups with the intention of having them blossom into Wall Street winners. Well, there’s a new kind of entrepreneur rising from the ranks of not just Main Street but that little subdivision well off of Main Street.


Spurred partly by inflation-induced need and partly by just wanting something to do (especially in retirement), America is fast becoming a nation of side hustlers. According to McKinsey and Company, the number of full-time employees operating side businesses has grown from 27% in 2016 to 36% in 2022.

And those figures don’t include retirees who have turned their hobbies into for-profit enterprises.

These people, and many more who are exploring the idea of starting a side hustle, represent the new face of the American entrepreneur. Gone is the image of the stoic, rugged individualist. The eager, optimistic opportunist has replaced it. And that’s not a bad thing.

But while that former pioneering spirit might have matter-of-factly endured the trials of tribulations of the trails they blazed, the new wide-eyed enthusiasm tends to lead to a roller coaster of emotions.

“It is stressful,” says Ryan Walicki, Co-Founder of Relish, in Beachwood, Ohio. “There are days we think, ‘Wow! We are on it! We are going to be the next Apple!’ Then, there are days when the question is, ‘What the hell are we doing?’ Stress management is in the macro belief that we are solving well-known business problems and we have the team to execute. The key to managing stress is maintaining the long view forward, appreciating what you have done by reflecting on accomplishments and ensuring your compass is pointing in the right direction.”

What are the cons of starting a side hustle?

One of the biggest concerns when starting a side hustle—and one you may not expect—is the stress associated with it. This worry is typical when venturing into any unknown.

“Starting a business can be very stressful, both mentally and physically,” says Charles Qi, Founder and CEO of StockPick in Toronto, Ontario. “Mentally, startup founders operate in unstructured and uncertain environments, which can be very stressful. Physically, founders need to wear multiple hats, which means multiple times the normal workload. However, founders can overcome all these if they truly believe in their vision and enjoy their work.”

Uncertainty breeds anxiety. Even if your side hustle started as a hobby, transitioning towards a revenue-generating model contains new and different tasks. The more moving parts, the bigger the chance one of the spinning wheels will break.

“It can be incredibly stressful to start a business, even when you’re confident in its success,” says Jeremy Babener, Founder of Structured Consulting in Portland, Oregon. “Something can always go wrong, and if you’re honest with yourself and acknowledge that, you’ll also consider your backup options. Good planning means less stress.”

Therein lies the solution to this problem. There are ways of dealing with stress that can help mitigate it.

“Stress is part of the journey for someone like me, who considers business to be a hobby,” says Ryan Neu, CEO, Co-Founder of Vendr in Boston. “Business stress is similar to a penalty kick in a tie game with five seconds left. If you make it, you’re a hero. If you miss, you’re going to be down for a while. Either way, that moment is electric. If you can find moments of enjoyment during stressful periods, you’ll increase your tolerance for stress.”

Is having a side hustle worth it?

Focusing on the upside potential, therefore, may house the secret to overcoming stress. Three yards and a cloud of dust may frustrate you. One step backward for every three steps forward can confound you. If you keep your eyes on the prize, however, all that interim irritation melts away.

“Everything worth pursuing is stressful and tough, but it depends on your tolerance,” says Kumesh Aroomoogan, Co-founder and CEO at Accern in New York City. “Starting a business is a marathon, and you’ll slowly build up resilience over a long period of time. This includes things such as: making payroll, raising funds to scale & grow, hiring & terminating employees, closing sales, improving your business metrics, building a scalable product, and much more.”

When you run a side hustle, you don’t have to worry about the stress associated with operating larger businesses. Still, you’re not immune from the fundamental stress experienced by all entrepreneurs. And, like them, the way out is very similar.

“It’s very stressful to start a business, but there should be some comfort in understanding that the hardest part is in the beginning,” says Nima Olumi, CEO of Lightyear Strategies in Boston. “Getting the early adopters and first paying customers to jump on your bandwagon and provide feedback so that you can build a more scalable long-term model is stressful, but it’s also rewarding in the experience it gives you.”

It helps to remember how you got to your side hustle. You didn’t just happen upon it. It came to you. It excited you. It embraced you. Feed on that feeling.

“You must have a passion for the business you are building, the customers you are serving and the problems you are solving,” says Jay Levy, Managing Partner at Zelkova Ventures in Miami. “If you love what your business is doing, this won’t eliminate the stress, but it will help push you through the challenging times.”

What is the easiest side hustle to start?

The easiest side hustle for you to start is the side hustle that most invigorates you from the very beginning.

Rafe Gomez, based in Montclair, New Jersey, is co-owner of VC Inc. Marketing (day job), but he also has a side hustle called Danceteria REWIND. He sees this from both a full-time business owner as well as a part-time side hustle operator. He says, “The most successful side hustle keeps your brain active and helps stimulate areas of your intellect that aren’t engaged by your ‘day job.’ It should be something that you can’t wait to dive into, and that—regardless of your mental/physical energy level—delivers pure happiness and excitement.”

How many hours should you put into a side hustle?

There’s a final aspect of stress you must address. This is not the stress of the situation or of the environment. It’s a stress that attacks you when you drop your defenses. What prompts this? The demands on your time during the initial start-up phase.

“There will be no one to rely on except yourself, and you will need to motivate yourself every single day to work hard,” says Michael Nova, Director of Nova Custom Printing in New York City. “You will need to network to meet the right people, and you will need to put yourself out there on a daily basis. You will need to spend more than eight hours a day working on your business. In a way, it’s like becoming a parent. The business will be your baby, and you will need to take care of it 24 hours a day. Are you up to the challenge?”

You won’t be reading this far if you aren’t up to the challenge. Specifically, the challenge is not to fight stress but to make it to your advantage.

“Everyone handles stress differently,” says Alex Adelman, Chief Executive Officer and Co-Founder of Lolli in Brooklyn. “It takes a certain type of person to start a business. Founders that do well are typically ones that can handle stress well. Stress is a natural survival mechanism. If channeled properly, stress can be a powerful tool that fuels you. Now more than eleven years in, almost nothing phases me at this point in my founder journey. I simply seek to understand each problem that arises, address said problem with logic and reason, and move forward. Zen and the art of building.”

Side hustles need not be philosophical undertakings. They should be fun and profitable. If you have butterflies, don’t worry. That’s a good sign. It means you care what happens.

And caring is the first step to succeeding.

Link to Forbes