Why Ignoring Side Hustles Because You’re Not Gen Z Could Be the Biggest Financial Mistake You Make This Year
Every day, it seems like there’s yet another young entrepreneur striking gold with their side hustle — and why not? In 2024, over a third of Americans are juggling side gigs to padded their wallets. Gen Z’s leading the pack, with nearly half diving into these ventures, while about a third of millennials chip in for that extra cash flow. But here’s the kicker — are side hustles really just a “young person’s game”? What about the baby boomers who’ve got decades of experience and possibly even less runway ahead than behind? I’ve been down this road too — back when side hustles were just called freelancing, I turned mine into a solid business that’s nearly hitting its 40th year. Trust me, a side hustle and a full-blown business couldn’t be more different beasts. The hustle? Usually a part-time, low-investment gig. The business? A demanding, complex machine that guzzles time, energy, and serious capital. But is there a blueprint for those seasoned entrepreneurs ready to pivot or ponder what’s next — whether it’s retirement, a new venture, or something in between? Let’s dig into the side hustle’s role beyond just the young guns and explore how it can be a powerful tool for reinvention at any age. LEARN MORE
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It seems that every day, there is another story about a young person who started a side hustle and hit it big. In 2024, over one-third of Americans had a side hustle to supplement their income. Side hustles are particularly appealing to Gen Z, with about half of them reporting having one. Millennials are a little less active, with about one-third of them stepping up to get that extra income that a hustle provides. Are side hustles just for those in the early stages of their career? Is there a huge opportunity for baby boomers as well?
Several years ago, I wrote an article and shared how I turned my “side hustle,” which at the time we called freelancing, into a business. At the time, I shared that turning a side hustle into a business does not always work. However, if you can go the distance, build a team and get the cash you need to launch and sustain the business you, like me, can have a great run. In 2027, Cynthia Kay and Co. will be 40 years old.
There are some dramatic differences between a side hustle and a mature business. To begin, a side hustle is generally a part-time endeavor to make some additional money and does not require a lot of investment. A business is more structured and complex. Believe me, it takes a significant amount of time, attention and cash to be successful in the long haul.
Most of the time, the side hustle stories are about an endeavor that grows and becomes a viable business. I would like to propose something to entrepreneurs who are at a different stage in their careers, where the runway in front of them is shorter than behind them.
There comes a time when entrepreneurs must decide to continue running their company or move on. Some entrepreneurs love the thrill of a new venture and cannot even think about leaving the business. Others get bored when managing the day-to-day operation and are ready to start a new venture. Finally, there are those who are ready to sell but struggle with the idea of retirement. I know I do. There are options.
Side hustle as a transition
A side hustle can be the perfect transition for entrepreneurs who are seeking a new adventure. If you have sold a business but are too young to sit on a beach, it might be a way to earn some cash while you consider the possibilities. A side hustle offers a flexible schedule, and you don’t have to make a significant investment. You can test out a big idea or new product and have the time to refine it. If it shows promise, it becomes your next entrepreneurial venture. If it fails, you still made some money and probably learned a lot.
Side hustle while working full-time
For years, people have been asking me when I am going to retire. Honestly, it is getting annoying. It started in my early 60s, and it continues to this day. I know many entrepreneurs who never plan to retire. That does not mean they will continue to work day-to-day in their operation. I have been working for years on a “side hustle” that gives me the best of both worlds.
While running my company, I built a communications consulting practice. I love to teach seminars, write books and speak to audiences, both big and small. I was intentional about building this side hustle because I know I cannot fathom retirement. Truthfully, like most entrepreneurs, there are some things I no longer enjoy doing at work. There are projects that do not require my advanced skills. I needed to step out of the way so that others at the company could step up.
Several years ago, working with my accounting team, I began to create a “business within a business.” All the activities that I was doing solo were line-itemed and separated out on the balance sheet. That way, we could account for all the income and expenses. More recently, I formed a new business entity where all that work now resides.
It is important to note that building a side hustle while working full-time running a company is quite different than doing it as a transition. I have made my established business the priority because there simply is not enough time to do both well. There are opportunities I have turned down. However, when I finally do sell the business, my side hustle is established and is ready to be supercharged.
Related: 10 Side Hustles for Retirees: Making Extra Cash on Your Terms (And Enjoying the Ride!)
Side hustle as an alternative to retirement
Entrepreneurs looking to work well into retirement should look at their existing business and determine if activities or services can become the foundation of a side hustle. In my case, there is no conflict of interest between my side hustle and my business. That may not be the same for others. In fact, if you sell, there may be strict non-compete clauses. Look for specific expertise that you have that no one else does. You may be able to carve out working with clients who will not stay with the company if you leave. There may also be short-term engagement projects that are a perfect fit.
Of course, a retirement side hustle can be completely different than the entrepreneur’s life’s work. It could be a passion. My father was a business owner, a dry cleaner who had a passion for duplicate bridge. Over the years, he became a life master. His side hustle in retirement was directing bridge games. It was great pin money, kept his mind active and he loved it. Others have hobbies that become businesses. It is easier than ever to set up ecommerce sites and sell anything and everything. Not creative? I know a retired teacher who has become a paid tester of products.
A side hustle is no longer just for Gen Z or millennials looking to build a career. It is for entrepreneurs of “a certain age” to stay engaged, make a little extra cash or a big haul and work as long as they want. To those who keep asking when I will retire, the answer is not anytime soon.
It seems that every day, there is another story about a young person who started a side hustle and hit it big. In 2024, over one-third of Americans had a side hustle to supplement their income. Side hustles are particularly appealing to Gen Z, with about half of them reporting having one. Millennials are a little less active, with about one-third of them stepping up to get that extra income that a hustle provides. Are side hustles just for those in the early stages of their career? Is there a huge opportunity for baby boomers as well?
Several years ago, I wrote an article and shared how I turned my “side hustle,” which at the time we called freelancing, into a business. At the time, I shared that turning a side hustle into a business does not always work. However, if you can go the distance, build a team and get the cash you need to launch and sustain the business you, like me, can have a great run. In 2027, Cynthia Kay and Co. will be 40 years old.
There are some dramatic differences between a side hustle and a mature business. To begin, a side hustle is generally a part-time endeavor to make some additional money and does not require a lot of investment. A business is more structured and complex. Believe me, it takes a significant amount of time, attention and cash to be successful in the long haul.
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