If you were asked to draw a visual of your career path, what would it look like? Maybe it’s a straight line from graduate to coordinator to manager to director. Or perhaps there was a step back to get an M.B.A., an amorphous shape for that much-needed sabbatical between jobs, maybe a parallel path where you picked up a freelance hustle in addition to your full-time gig.
You almost certainly wouldn’t see what Kelly Vaughn does when she takes a look at all the twists and turns of her career journey, or assesses all the hyphens she could add to her job title: Director of Engineering at Spot AI, former founder and co-founder, consultant, advisor, educator, and author. It’s not a line, it’s not even a diagram – it’s her own bonafide masterpiece of accomplishments, challenges, passion projects, and paychecks along the way.
It’s not the traditional progression that matters most to Kelly, but rather the growth and joy experienced in doing a little bit of everything. After eight years of full-time entrepreneurship, Kelly recently made the transition back to full-time employment with her current role at Spot AI, a decision she’s incredibly pleased with. “As someone who has always owned the entire problem and has not had the opportunity to share it with somebody else, it’s nice to have a shared burden.”
The shift from founder to full-time employee doesn’t mean Kelly’s dropped her self-described “founder’s brain.” Instead, she’s learned how to harness those entrepreneurial superpowers at her current role and all of her passion projects along the way – starting with finding joy in what she’s working on.
Joy as a compass
Kelly got her first job at the age of 14, having taught herself how to code when she was just 11 years-old. The gig was right up her alley: coding an online catalog in exchange for a t-shirt that she still has to this day. More than the job itself, that first window into the working world spurred an entrepreneurial mindset that set Kelly on a trajectory to grow her career and eventually her consulting business. While she’s never fit into the traditional mold of a “day job” until recent years, she’s adopted the idea of leaning into joy as a guiding principle for how she approaches her side hustles.
“I think what's most important to remember when it comes to Polywork, [is] it's not necessarily actual work that you're putting in the time to get paid a certain amount of money,” Kelly explains. “It's also what do you enjoy doing on the side? What really brings you that joy?”
For Kelly, that joy was ready to be uncovered in the process of writing a book. Becoming an author was something she had set a goal for, and in 2020 she did just that. Kelly self-published “Start Freelancing Today,” which boasts a five-star rating on Amazon and offers tips, tricks, and Kelly’s own story as a guide to help readers navigate the world of freelancing, from finding clients to drafting contracts, and mediating challenges as they arise.
“I think what's most important to remember when it comes to Polywork, [is] it's not necessarily actual work that you're putting in the time to get paid a certain amount of money. It's also what do you enjoy doing on the side? What really brings you that joy?”
The first draft of the book was written in just one month, and she had such a great time doing it, she’s considering drafting another – this time focused on start-up failures and all the lessons learned during the process of building and scaling.
Timebox and time manage
Writing a book in one month is no easy feat, and would simply be impossible without absolute deference to rigid time management. When Kelly set out to write “Start Freelancing Today,” she set one simple rule: write the first draft in one month. While a 30-day timebox on such a lofty goal can seem daunting to many, it also helped make the goal feel achievable – and lo and behold, she did it. In just a month, a first draft was on its way for a friend to edit, before opening up pre-sales and self-publishing.
Kelly’s astute management of her own time isn’t limited to creative pursuits like book publishing; rather it’s a skill she’s developed by necessity. As she balances full-time work with a steady stream of freelancing opportunities and creative pursuits, Kelly assesses her calendar regularly and itemizes her time. Whether she chooses to take on a project becomes a matter of what time she can afford, which can be informed by any number of factors including how much time her current full-time workload is consuming, where she is in the world (if she’s working remotely, she may want more unstructured time), and what other projects she currently has in the mix. It’s this fundamental mastery over her calendar that empowers her to work to her fullest potential.