In 2012, two years into a job at international advertising, marketing, and public relations giant Ogilvy, Grant Tudor got a call from a friend he had met while studying in Nairobi. The friend was looking to brainstorm ideas for an organization she was running in Kenya that used mobile communications as a violence prevention and intervention tool. “How do we methodically increase our subscription rates?” she asked. And “How do we craft messages that more dependably influence behaviors?” Grant immediately envisioned himself back in Kenya, putting his marketer skills to work in a radically different context. In that moment, the genesis of Populist—Grant’s side gig—was born.
As with many Millennials who have ambitions of doing more with their career than simply climbing the corporate ladder, Grant faced the agonizing dilemma of choosing between a job he very much needed and a passion project he wanted to pursue. Or did he? Is it really that clear cut—the job you need to pay your bills or the opportunity to make a difference?
Wisely, Grant chose a direction that has enabled him to both keep his job and launch Populist. Rather than quitting his job and rushing to catch the next flight to Nairobi, Grant prepared a presentation on the pros and career upside for Ogilvy of giving him time off—and a few weeks later, with Ogilvy’s support, he was in Kenya, cross-applying his marketing strategy skills in an entirely new terrain. It was the career catalyzing moment Grant dreamed it would be and he knew it wouldn’t be work-as- usual when he returned to his office in New York City.
Holding down a day job while hustling the passion project can be done—if you can check your ego and apply yourself to completing both jobs at hand. A side hustle involves going the extra mile for your current employer and banking the trust of managers and workplace colleagues, an irreplaceable asset that you’ll need when you finally decide your side gig is the full-time passion project.
Working through building how to build her brand and business—while employed—has been one of the most challenging, yet professionally rewarding things Tiffany Tibbott has accomplished. Tiffany was a merchandiser at Juicy Couture and then a vendor manager at Beyond the Rack before she launched The B. Side, her innovative swimwear company, in 2015. Tiffany worked her corporate roles to their fullest to be able to make the leap from corporate:
“I was always using the resources around me to learn how I could grow my idea into a business. I extended my outreach and networked tremendously, befriending anyone I thought could help me take my idea to the next step. From suppliers, vendors, technical designers, advisors, and other experts I used my corporate contacts to pick the brains of the best and brightest! It wasn’t until I had a final prototype in my hand of my first B. suit that I decided I needed to leave corporate. It wasn’t an easy decision, but I knew it was best for The B. Side and my former employers.”
Trust played a huge role in Grant’s ability to move Populist forward. First, he gained the trust of peers inside of Ogilvy who believed in his vision and were prepared to dedicate after-hours free time to working on projects for Populist. Second, he won the trust of senior leadership who would be instrumental in removing internal corporate policy roadblocks, so Populist could officially launch. Had Grant not earned that trust, Populist would have been permanently relegated to a side project.
Dreaming about moving your own side project from the back-of-the-desk-drawer to front-and-career-center? Here are some suggestions:
1. Keep Hustling Your Day Job
While your heart and soul may be longing to work exclusively on the side gig, put all your efforts into your job when you’re on the clock.
2. Build Support Networks
An idea without a network is simply an idea. For Grant and Populist, the agency network of support has been everything. He adds: “Relationships with people who like you enough to give you their time, and like your idea enough to associate themselves with it, has probably been the single most important ingredient so far.”
3. Remember There Is Power in a Paycheck
When you’re not worrying about how to pay the rent, you can focus your extra time strategically. As Grant found with Populist, his ‘real’ job made it easier to make thoughtful, healthy decisions and to say no to clients who weren’t a good fit—something he probably wouldn’t have done if he had bills or payroll looming over his head.
4. Be Resourceful and Egoless
If you want to make something happen badly enough, don’t let your ego get in the way. Since leaping from a paycheck, Tiffany has taken jobs babysitting, consulting, bartending, and even working at a fitness studio to help fund The B. Side and to continue to live in New York City.
5. Talk About Your Idea
The default at work when we fear repercussions is to not say a thing. Silence shields us when we fear our ideas will be mocked or worse, crushed by colleagues. However, there is tremendous value in seeking feedback and guidance from those you work with on a daily basis. It shows those outside the workplace you can effectively sell your idea—and yes, it builds that all essential trust.
Finally, be prepared for some unexpected upsides from all your hustle. Sure, having a full-time job while juggling a side project and a personal life is a challenge no matter how skilled you are at time management. The upside is, you may just become better at devoting your time to all three of these priorities. According to Grant, he feels he has more time now as he wastes very little of it. He adds “I’ve become so much more conscious of time. And when you begin putting a real premium on time, I think you’re able to more thoughtfully parse it out.”
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