When the topic of side hustles was broached in an editorial pitch meeting, two things came to mind: First, this calls for a killer promo image prominently featuring bell-bottoms (see above). Second, I have so many notes. As a freelancer juggling multiple jobs, I survived by trial and error. I had major coups and successes, and plenty of hurdles. From learning to bid a project to chasing down invoices, the whole experience was new to me. Keep scrolling to hear my inside tips on how to get it all done.
I know. The word transparency is bandied about today’s corporate environment with such frequency that it’s beginning to sound banal. However, as cliché as this may sound, transparency is essential. If you have a full-time gig and are spreading your wings beyond your day job duties, you need to loop in your employer. Review your contract meticulously. Do you need to negotiate a carve-out to legally take on extra work? Clearly communicate your goals and outside commitments to both your direct supervisor and HR. Once everyone is looped in, get it in writing. I would personally advocate hiring an attorney or business manager to batten down the hatches. Once you start juggling extra work, you’ll need to effectively communicate your schedule and availability to all parties, including new and existing clients. Set up weekly or biweekly check-ins to ensure you’re keeping pace and all the trains are running on time.
Get up close and personal with stats and analytics. Research your industry. If you’re starting a side business that’s based on creative work, for example, the pay scale can be all over the map; there are countless considerations and multiple metrics for measuring worth. And while it is scientifically documented that men are more apt to talk about their salaries than women are, you should get over any shyness you have around asking others in your industry what they charge. Ask around. Ask what people charge. Ask what people pay. If you can’t broach the subject, google it. There exist a host of websites that can quote you the average and median salary for any job, based on location. You want to throw out a number that’s reasonable, and it may be a sliding scale. Creative work is like seafood—it’s always market price.
Especially if you have a full-time gig, budgeting your time and resources is the biggest hurdle of getting any side project off the ground, so you will need to consistently evaluate where your shortcomings and time-sucks exist. The 80/20 rule is real; expect 80% of your payoffs to come from 20% of your efforts. Creating a business is a series of advances and retreats, and you should always be thinking how to build a better mousetrap. Detach from the ego of failure and missteps and view everything as an opportunity to improve. Anyone successful has consistently reworked the plan. Love your starting point. Execute your plan. Evaluate it. Then move on to Plan 2.0. Be ruthless and impersonal with your results. Odds are your side business is a passion project, which offers the perfect opportunity to get über-self-critical and personally attached. But remember: It’s not personal. It’s business.
If your second gig requires you to do your own invoicing, it can be a substantial and consistent chunk out of the workweek. The best way to combat the inevitable malaise and frustration of having to take valuable time away from your schedule to handle billing is to have a standing appointment. Do it every Sunday at 3 p.m. Pick a time and stick to it. Include your payment schedule at the bottom of the invoice: e.g., "payment due within 30 days of receipt." In the event the payment is late, have a structure in place. Include late-fee terms. You want everything in writing and upfront. Always send your invoices on the same day of every week, month, etc. Your clients will love you for it.
When I started out, 100% of my business began through internal referrals and word of mouth. It’s human nature. Everyone loves a vouch, so a personal relationship will often give you a leg up on the competition. And let’s be real: The business world is cutthroat and competitive, so any advantage to minimize risk is a huge asset. Trust and reputation are your highest currency. If your full-time employer is supportive of you pursuing your budding interior decorating business on the weekends, ask her if she knows anyone in nesting mode. Never burn a bridge, and always operate out of integrity, which is more than just ethics; it’s honoring your word. The adage “under-promise, over-deliver” is a golden oldie, but what’s most important is to deliver.
Build your personal relationships and maximize your network. Cruise your LinkedIn connections. Ask for an introduction to someone who can help you. You’d be surprised how many people will take a lunch. If you want an in with a company or tastemaker, figure out if the two of you have a mutual connection. If you absolutely have zero degrees of separation (in today’s modern world of overly documented connectivity, I’d say this is unlikely,) cold-email someone at the company. Have I heard stories of people joining exclusive dating app services purely to meet employees at Google? Yes, yes, I have. Is this out of integrity? I’d argue yes; however, it is what you’re up against. Start dating your career.
This is a simple one, but it’s astounding to me how many people underestimate the power of the calling card. Invest in your cards with a Patrick Bateman level of scrutiny. Go ahead and hem and haw over the typeface and exact shade of ecru. Get it right. It’s going to be passed around, and yes, aesthetics matter. That’s not to say you need to go overboard. Sleek and understated can slay. The key is to be deliberate and avoid a template.
Never attend a social function without a business card. Work events you attend for your full-time gig could prove to be great opportunities to acquire new clients for your side gig and vice versa. Promote both businesses wherever you go, and everyone will be happy. If you’re going to a dinner, keep a fresh stack on tap. You never know who you’re going to meet. Mingling in the wild is a far better environment for selling yourself than any boardroom is. Don’t leave home without something tangible for a perspective client to take away. Also, honestly, you just look more legit.
Don’t take any wooden nickels when you sell your soul. The Eels said that. I think it works.
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Have a tip for keeping a side project afloat? Tell us in the comments below.