What to Do When Your Side Hustle Overtakes Your Day Job—Tips from 5 Side-Hustlers-Turned Entrepreneurs

What to do when your side hustle overtakes your day job

‘Side hustle’ has become a ubiquitous term—almost 50% of millennials have one. There is boundless information dedicated towards what side hustle you could start, how to balance your day job with it and how to grow your fledgling business. But what happens when your side hustle is so successful that it’s encroaching on your day job?

What to do when your side hustle overtakes your day job

Organizational effectiveness consultant Penny Castle has some insight for those whose side hustles are becoming unmanageable.

“Firstly, consider whether your current employers could be secured as a client. There’s also the option to use flexible working practices to your advantage, such as negotiating fewer working days or hours.”

Castle also suggests applying Martha Beck’s 5B technique: 

  1. Better It: Try to make what you are doing more efficient.
  2. Barter It: Barter service or product offerings with other businesses.
  3. Buy It: Buy a service, like a virtual assistant.
  4. Batch It: Batch time-consuming business elements together, such as invoicing.
  5. Bin It: Toss activities you’re spending time on that don’t move the needle. 

So what does this look like in practice? We spoke to five entrepreneurs whose booming businesses began as side hustles. Although each of them eventually went full-time with their side hustle, each applied various coping mechanisms, including those outlined above, to tide them over until the time was right.

What to do when your side hustle overtakes your day job

Simon Alexander Ong was working in the financial industry just before the global financial crisis of 2008. His side hustle was his coaching practice. The company he worked for, Lehman Brothers, collapsed just 14 months after he joined as a graduate. Momentum was building due to coaching multiple clients and speaking at more events. Simon loved connecting with like-minded people, and got excited at the prospect of going full-time.

“My energy was being drawn more to the development of my side hustle than my corporate career,” he says. However, it took several years before he exited, and it was more a result of circumstance than choosing a perfect moment. “If I had won one more client, it would have disrupted the balance I had between the two,” he explains.

In his coaching capacity, his advice for those considering moving full-time with their side hustle is visualization, where you imagine that the last five years have been the most memorable and magnificent years of your life. “What would you be telling me has happened in every area of your life for the past five years? More importantly, how has that side hustle of yours evolved and what does that tell you?”

What to do when your side hustle overtakes your day job

Anna Cargan was a family law solicitor who started a side hustle in the form of Buildabundle, a second-hand children’s clothing shop, and swiftly experienced the stress of an exploding side hustle. “It quickly became too much to manage on my own with a demanding job and three very young kids. There weren’t enough hours in the day, and I was becoming burnt out,” Anna says.

For Anna, help arrived in the form of partnership. “My best friend came on board, and we became equal partners.” She also expanded her side hustle by hiring staff to take care of business during the day, while she and her partner took over in the evenings.

Anna also felt paralyzed by indecision, which made her reluctant to leave. “I’d worked really hard to qualify as a solicitor, and I did enjoy my job.” She tried reducing her hours, but ultimately, needing a work-life balance became important. “I needed to get my evenings back and spend more time with my husband and the children, so I handed in my notice,” Anna says.

What to do when your side hustle overtakes your day job

Maddy Alexander-Grout was a change-management executive when she started her side hustle My VIP Rewards, designed to help parents save money wherever possible. Her boss allowed her to reduce her day job to three days per week, but her decision to go full-time with her side-hustle was forced on her when she was made redundant.

Her advice is to make sure you are financially stable and can pay yourself before you quit. “I had no choice but to make it grow, and there were some stressful times, but it was totally worth it.”

What to do when your side hustle overtakes your day job

Nick Hems, a personal brand stylist, used to be a marketing director for an insurance brokerage company. He saw a gap in the market for targeting men’s style in relation to their brands and capitalized on this opportunity by reducing his work hours to three days a week. “I also made the decision to politely drop a couple of clients as my styling work was now taking over 50% of my time,” Nick says.

His wife supported him with marketing and administration while on maternity leave after the birth of their son, and he recently expanded his team. “There were still opportunities I knew I was missing out on but didn’t have enough time to take advantage of. These stylists have similar vision and values, so they can help me grow the business.” Nick is a big believer in the power of making a business plan and placing it somewhere you will see it frequently. “Don’t just work in your business, but on it too,” Nick says.

What to do when your side hustle overtakes your day job

Amber Leach was working full-time as a digital marketing officer and side hustling as a wedding photographer. “I realized I didn’t want my daughter to be in childcare every day for the rest of her life. I’d been taking photos for friends’ weddings, so I set up Liberty Pearl Photography,” Amber says.

To cope with the growing photography side hustle, she reduced her hours to part-time but eventually handed in her notice.  “I would never have grown as quickly as I did without the team around me,” she says. And grown she has, having captured over 300 weddings with a team of five photographers.  

She has also made use of outsourcing tasks such as editing and administration in order to save precious time. “I wish I’d worked for myself sooner,” Amber says. “If I’d started this at 20, I could have put all that overtime into my own business.”

While most booming side hustles will eventually beckon their creators to a full-time position, there are no two that are quite alike. Your side hustle may benefit from you reducing hours in your main job, hiring staff, entering a partnership or outsourcing administration—but only you know what will work best for your business. 

But while you consider how best to juggle the growth of your side hustle with your day job, remember to take a moment to appreciate how far you have come to be in the position to make these decisions. It’s a moment of pride and achievement, so take some time to appreciate your development before you make your next big move.

Photos courtesy of Penny Castle, Simon Alexander Ong, Buildabundle, My VIP Threads, Nick Hems, and Liberty Pearl Photography

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Tayla Blaire is a South African freelance journalist and copy/content writer for lifestyle brands. She has written for both print and digital publications such as Refinery 29, Insider, Huffpost, Stylist, Glamour, Buzzfeed, EQ and more.  As of 2022, writing remains her side hustle while she works full time as a high school English teacher. She is passionate about helping others grow their side hustles, especially when they start out as passion projects. You can find her on Twitter or at www.taylablaire.com

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