How do you know when you’re ready to make the leap from side-hustle to replacing your day job?
by Kate Lindsay
In my life, I can remember three major “now what?” moments: When my parents dropped me off at college, when I moved into my first apartment in New York, and a few months ago, when I decided to go full-time as a freelance writer.
Career-wise, my trajectory has been pretty traditional, going from an internship to a series of full-time jobs. There have been bumps along the way, of course. I juggled my internship alongside a retail job to the detriment of my weekends, and two out of my three full-time roles have ended in being laid off. After the first layoff, I got back on the horse. However, when I was laid off earlier this year, I wondered: Is this horse even worth getting back on?
Rather than frantically applying to full-time writing roles, I decided instead to see if I could hack it as a freelancer. I was so burned out from working staff jobs throughout the pandemic and realized that making my own schedule and being my own boss could be just the change of scenery that I needed—even if I didn’t have the faintest idea how to do it.
Content creators often face a similar crossroads. What begins as a side-hustle can become lucrative or fulfilling enough to replace your day job. However, it can be hard to know when you’re ready to make the leap.
“For me, the ‘right’ time turned out to be on the verge of a pandemic, right after I said goodbye to grad/med school and moved halfway across the world,” Brianna Leegan, a marketing and business alignment coach, says over email. While her decision to take her business full-time occurred during an uncertain moment, she knew her heart was telling her to take the plunge. “My advice would be to stop waiting for the ‘right’ time and follow your inner knowing, that voice within you that says it’s time.”
Even if you are able to successfully listen to your inner voice, then comes your “now what?” moment. We spoke to some experts who broke down the best ways to prepare yourself for full-time content creator life, and shared their tips for how to stay confident once you’ve made the leap.
Gather experience: This may seem obvious, but it needs to be said: Don’t quit your day job to become an influencer if you haven’t built up a following or ever worked with brands. Specifically, Johanna Adriaansen, an online educator and coach specializing in personal branding and business, says aspiring full-time content creators should make sure they’ve done paid work with brands before leaving their other jobs, not just received gifted products.
“This will give you exposure to the actual path of getting paid as a content creator,” she says. “Having experience with the negotiation and contract phase is very valuable!”
Think of the switch from day job to full-time-freelance as less black-and-white, and more a gradual transition as you build up your content creation and wind down the day job you’re looking to leave.
Give yourself a financial buffer: No matter what your inner voice may be saying, you definitely don’t want to quit your day job without any other income saved up.
“If you quit your job now and without any other income [and] you know you aren’t able to pay next month’s bill, then you’re probably not ready,” Adriaansen says. “But if you know what your income goal is and you are already making half or three-quarters of that then it’s time to take the leap.”
Leegan agrees that for full-time content creation to become sustainable, you have to start with a financial cushion, rather than “rushing yourself to create enough revenue from your brand new full-time business just to keep yourself afloat.”
Be proactive and confident: That first day as a full-time creator may feel like a dream come true—or it may have you worrying you made a huge mistake. Having the whole wide world of influencing before you can be intimidating, which is why Adriaansen says it’s important to remind yourself of your brand and purpose.
“If you aren’t sure where you’re going or what you want that to look like then you can end up treading water and desperately looking for someone to tell you what to do,” she says. “We need to treat our brands like a business which means knowing how we serve and why we do what we do.”
Specifically, that means having a clear, up-to-date content calendar for yourself, and actively researching and pitching the brands you want to work with to increase exposure. Adriaansen also recommends collaborations with podcasts and fellow creators as other methods of getting your name out there.
Inevitably, though, with all this outreach and experimentation, not everything will work out the first time. In fact, so much of freelance life is being met with “nos.” Keep pushing.
“Running a business full time is not a walk in the park,” Leegan says. “To be successful, you have to be able to get back up each time you fall.”
Don’t forget to rest—and celebrate: When you’re working for yourself, you may think that means it’s easier to do less work, instead of more. However, I personally find that’s rarely the case. Too often I’m pushing myself to complete “just one more” task at 7 p.m., instead of enforcing a hard 5 p.m. exit to relax and recharge.
“The passion and a lack of work-life boundaries can mean eight-plus hour days,” Leegan says. “However, eight-plus hour days can result in burnout and a lack of creativity. And a lack of creativity can make it very hard for creatives to create their best work.”
Working hard is important, but playing hard is, too, especially if that means celebrating the very thing this whole article is about: You’re becoming a full time content creator! Adriaansen reminds creators to stay positive and encouraging.
“Heck ya babe. You’ve already come so far,” she cheers. “Trust you know what you’re doing. Keep being intentional with your brand, continue to strengthen your craft, and stay true to you. You got this.”
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