8 Tips for Starting a Successful Side Hustle at Any Stage of Life

We spoke to women who started businesses later in life (and are now Katie’s Shop brands!).

If you’re the type of person who has lots of hobbies, or even just one hobby you’re particularly passionate about, we have a question for you: How many hours have you spent fantasizing about turning your true passion into your full-time job? Hours when you were supposed to be focused on your “real” job or when you were creating something you love only to give it away to a neighbor for free. Perhaps, you’re thinking about how you can put your baking skills to great use or share your eye for fashion with the masses. 

Maybe it’s time to give that fantasy a whirl in the real world. We’re not suggesting you just up and quit your job right now; many people start businesses in their spare time, gradually building a brand in small increments. Given today’s economic climate, we wouldn’t blame you for going that route before giving up your steady income for it.  

However you do it, starting a business can feel like a daunting task — zooming in on just the right product, finding the courage to get started, finding the money (and then managing it), learning how to properly market your brand, dealing with clients, ensuring product quality — we’re already breaking a sweat just thinking about it. It’s not easy, but it’s also not impossible.

If you think it’s too late for you to start a business you’re wrong — and we have the proof. We spoke to women who launched their own companies later in life after moving on from their previous careers and women who nurtured a passion project in their spare time. What do they all have in common? They all now have burgeoning brands that started as side hustles. 

After surviving leukemia, Lynne Fletcher O’Brien started Line in the Sand at age 57, a protective and active waterwear line, so that people like her who are concerned about sun exposure could have swimwear they feel comfortable in and focus on enjoying the water. Meanwhile, sisters Hala Yassine and Farrah Haidar, who immigrated to the United States as young girls, tapped into their ability to bake delectable sweet treats to start Seven Sisters Scones as a side hustle. When they started, Yassine was 50 and Haidar was 40, and they were both juggling full-time jobs. Beauty experts Lorrie King and Celeste Lee decided they would focus their energy on finding skincare solutions for older women based on hormonal changes in the body, setting up Caire Beauty. Back then, they were in their late 40s and were well-versed in the challenges facing women in their later years. 

They have advice for the rest of us on what we should keep in mind if we want to turn a hobby into a side hustle. 

Get ready for a serious commitment

“Get ready to put your heart and soul into something,” says Yassine. “Because if you’re not, it’s not worth it; you are going to be idea poor, money poor, time poor. But anything you put love into will grow.” 

When Yassine started Seven Sisters, she was working from home on program management for a company, meeting some clients as a therapist (yup, she also has a Ph.D. in clinical psychology), and taking care of her two children. It was never going to be easy. But she was committed. In the beginning, she worked 17-18 hour days, compromised many nights of sleep, and turned her home kitchen into a scone-baking arena.. 

While building Line in the Sand, O’Brien spent many nights with her new best friend, Google, searching for the right material for the swimwear, learning new skills, and developing the connections she needed to start her business.

Anticipate evolution 

Yassine says building a business is “kind of like having a baby — you have all these hopes and dreams and then the baby grows up and you realize this is not what you had imagined.” She believes it takes a life of its own. “If you’re open to understanding it [the business] and loving it for what it is, it’ll be fantastic,” she says.

So, once you pour your love into starting something, you have to be open to learning, growing, and iterating. You can’t be attached to your idea of what the business was supposed to be. Instead, you have to accept it for the life it takes on. 

Seek out mentors and connections

We know it can be hard to approach strangers, especially in this post-pandemic world. But, sometimes, that one cold email to a stranger can be a game-changer for your business. O’Brien says she realized that “people just want to help.” 

She recommends using LinkedIn to reach out to people who could guide and help you in your journey. Look for like-minded individuals who are further into the process, whether they launched a small business successfully or work in a major corporation in the same industry, or reach out to people you look up to. Don’t wait for a mentor to fall into your lap — as O’Brien puts it, you have to “create mentors for yourself.

Know your resources

Caire Beauty founders King and Lee relied on outside resources to learn how to start and grow a business. Many of these resources are free, such as Y Combinator’s Startup School, and there’s no reason you shouldn’t use them. 

And the resources look different for everyone — it doesn’t have to be a fancy accelerator or startup school. For O’Brien, her resource was a children’s book, What Do You Do With an Idea? It gave her motivation and energy right from the start. 

You can also get tips from successful entrepreneurs at Mixergy or join the conversation in a forum like Quora’s page for Startup Founders and Entrepreneurs.

Go out there and find the resource that works for you. 

Decide how best you can fund your venture 

Putting down the money can be scary — all the up-front expenses, raw material costs, staff salaries. Ah, that sounds like a big jumble of frightening numbers. 

Hold on though, it doesn’t have to be so frightening. It’s important to realize that everyone has a different path when it comes to funding their venture.  O’Brien was fortunate enough to be able to use her savings to kickstart Line in the Sand.

Yassine and Haidar did the same. “We invested in ourselves,” Yassine says. The sisters decided how much they were willing to part with, and invested exactly that.. With that initial investment, they gave themselves a chance to make Seven Sisters Scones work. They also took a loan as a precaution to help with expansion, but they never ended up using it. They spent years reinvesting what they were earning to expand and get the equipment they needed. In four years, the business started funding itself and turned profitable. 

But, that’s not the only way. Lee and King entered a series of start-up competitions to fundraise for their venture. They entered a number of funding and pitch competitions — they won some and lost some. Eventually, they were able to take Caire into the Entrepreneurs Roundtable Accelerator, and it changed everything for them. 

All of this to say that there isn’t one journey that’s right for everyone — different founders find different ways to kickstart their initiatives. Start by identifying what’s right for you; it could be venture competitions, loans, crowdfunding, or any combination of these and other funding options. 

Be prepared to do it all 

As a small business owner, Yassine does everything — you can find her baking, cleaning, sweeping, answering phones, managing clients, or preparing orders for shipping. Even a few years in, with a team to support her, she stays grounded in what it means to run a business: You have to be ready to do it all. 

So, when you start something, be ready to take on whatever task the work demands. In fact, according to Yassine, doing it all gives her an opportunity to figure out all the different aspects of the business. 

King and Lee agree — they believe it’s important to “get in the weeds yourself.” In this very digital world, it’s easy to hire consultants to manage and help you grow your business. But a great deal of learning comes from jumping head-first into the waters of entrepreneurship.

Reach out for support when you need it

Yassine and Haidar will never forget the time they were featured on QVC — it was a huge deal. They knew this meant they would see orders skyrocket over the next few days, and they would need all the help they could get to keep up. As Yassine put it, “We were small potatoes at the time. In any given week, we were baking and selling about 2000 scones. QVC hit and we had to go from 2000 to 25,000 in four days.” 

So, they had to rework everything and figure out the operations to make this possible. They turned to their family and friends for help, who then helped the sisters deliver thousands of scones. 
So, sometimes you’ve just got to lean on the pillars you have. Simply put, don’t be afraid to reach out for the support you need. 

Remember why you’re doing this

We know starting a business is hard, especially when you have so much going on — kids, work, life. Is there any time to sleep in there? O’Brien faced countless hiccups when launching her brand: There was a pandemic that led to shipping issues, one of her factories was looted, her thread was stuck in Japan, and her fabric was stuck in Italy. 

Despite obstacles, focusing on the small victories kept her going. “I get a few emails at least every week that really rock me to the core and remind me why I’m doing this.” For her, that means she gets emails from women who tell her they haven’t been at the beach for 10 years, but are now able to because they feel comfortable in her swimwear line. It means messages from women who believe Line in the Sand waterwear is freeing and feels like a second skin. Most importantly, it’s the messages from cancer survivors who can now be back in the water without worrying about skin exposure. 

Similarly, for King and Lee, it’s all about their mission. They wanted to build a “pro-aging” skincare company that focuses on giving women effective, affordable products, with benefits backed by scientific research on hormonal changes in women’s bodies. For them, it always comes back to their purpose — it’s what keeps them going. 

So, when you begin, ask yourself whose life you want to impact. And when the going gets tough, remember why you started this journey, and think about each person you’re impacting.