July: Side Gigs and Side hustles
Elizabeth Coopersmith, Rising Tide Society Board of Directors
Dawn Smith is the owner of Whole Life Solutions, where she offers career transition coaching and relationship coaching services. She is a motivational speaker who has spoken at numerous conferences and organizations, and on the 2024 TEDx stage. She’s a wedding officiant, which is how I first met her when she joined my chapter, Rising Tide Pasadena. And she also runs a local youth center. In other words, she’s the perfect person to discuss multi-gig management with.
The first thing Dawn said to me after she read my questions was that she has a tough time with terms like “side gigs” and “side hustles,” that whenever she talks about money-making ventures, that’s just another career path or pursuit. That’s where we started.
EC: A lot of the work you’re doing right now is wonderfully diverse, from running a youth center to officiating weddings to career coaching. How do you balance these multiple career pursuits without losing focus?
One of the biggest things that I try to, I don’t know if “dismantle” is the right word, but I think many of us were brought up to believe that you’re supposed to have “a” career, right? And everything else is a hobby, a side gig, or whatever – not as meaningful. And I think that whole concept is a myth. I’ve never not had more than one career path going on at a time; I can’t think of the last time. For me, everything I do has one through line, which is supporting people at really pivotal moments in their lives. So, even though everything is wildly different, from marrying people to helping support a hip-hop center, to career transition coaching, it is all about helping people find their places of belonging and alignment. That’s how I maintain my focus.
The nitty-gritty day-to-day comes down to setting a big-picture goal: what are you trying to measurably achieve in each pursuit? Then, you work backwards in these tiny steps, making sure to touch on everything regularly, and have daily and weekly rituals where you regroup and check in with yourself on what the next goal is for each path.
EC: So, when you’re figuring out how to successfully balance multiple career paths simultaneously, what adjustments—day-to-day scheduling, mindset, or anything else—are the most important if you want to sustainably scale them?
Most of my clients have ADHD or are very creative problem solvers and thinkers. They have multiple ideas that can feel daunting and overwhelming. I help them discern, ‘Am I trying to build in multiple things because I’m scared?’ Or am I taking on new pursuits because I’m equally passionate about all of them and feel like there’s actually an interplay between them all? There’s a huge difference between keeping a lot of things afloat because you’re worried none of them are going to pan out, versus being a multi-passionate person creating different money-making paths.
The next most important step is being very intentional about who your audience is for each of your career pursuits.
There’s a tendency, when you become an entrepreneur, to cast a wide net because we feel like, “I’m new, I need to make money, so I need to bring any clients on.”
I’ve attended networking events where I might meet a dozen photographers. And I ask, “Hey, who do you primarily work with, or what’s your style?” When people are just starting out, they’ll often say something like, ‘ Oh, whoever needs a photographer for their wedding.” I don’t know who I can refer them to. But if they say, “I do black and white photojournalism,” or “I only work with really bold, edgy couples”, or “I have a very colorful style”, and then I do know who to send them to. Knowing exactly who your absolute ideal fit is and where they are looking for support is crucial to growing and scaling any business.
EC: What if the financial fear is legitimate? If you really do need to make more money?
Oh, that’s absolutely valid. If you’re not acting out of fear, you want to pursue a new path that you’re passionate about, but you’re legitimately worried about how pursuing this will affect your finances? Gather enough information, create a budget, so you can make an educated guess about the potential income from your new venture. Create a realistic financial plan to understand the ramp-up period for the latest business and how long it will take to become sustainable. You can still hold on to the current job or a temporary job as a stepping stone to pay the bills until you get the new things going. And it could be better if it’s a job you don’t love, that’s not close to your passion, so it won’t drain or dilute your energy. You’ve done the research, and you have a plan to stay financially stable in the meantime.
EC: As someone with ADHD and anxiety yourself, how have you structured your routines or habits to manage your multiple careers?
It comes down to being extremely mindful of what the most important things to get done are each day. I take micro actions very seriously. I use a “shutdown ritual” to do this. – I do a five-minute brain dump, writing down everything that my ADHD anxiety spaghetti brain feels needs to get done.. Personal things: I’m a single mom to two sons, we’re in the middle of moving. I create art, I work on various projects, follow up with clients, and other tasks related to my active career paths that need attention now or soon. There will probably be 10, 20, or 30 things on this list. I rank them and pull out the ten most crucial, and focus on those for that day. Just pull a handful of things that are so vital that as long as they get done, you’ll feel like you had a productive day and are on top of things. Everything else can wait.
That’s been most helpful for me, because it’s so easy to get into analysis paralysis. I need to set out each day with a list of tasks and actions that are very small and very concrete, and that will hit notes in all the different areas of my life.
I also start the day with a morning ritual. I was talking to a new friend and told him, “So I roll out of bed and I go outside and I do this thing,” and he said, “Every morning?” I said, ‘Yeah,’ and then I go work out, and he’s like, ‘Every morning?’ I said, yeah, there’s no way I would manage my ADHD and anxiety without this structure. And you’d think, ‘Okay, you’ve got three jobs, do art, help run a youth center, have two kids, you must work 10, 15, 20 hours a day, right? ‘ I don’t, and this is why. Again, it depends on the day, but I usually work around five hours each day.
EC: What criteria do you use to help overwhelmed professionals decide which career paths are worth pursuing?
Start by choosing the paths that truly capture your attention, especially if they share a common thread. Again, I’m being biased towards people with ADHD, because boredom is our kryptonite. It is! Therefore, having only one focus is often less sustainable because it’s harder to stay engaged.
EC: What practical strategies can anyone use to avoid burnout when they’re juggling multiple career paths and other responsibilities?
Work out, even if it’s just five minutes at home! Build physical activity into your day. It is statistically the single best thing you can do, other than medication, that has a significant impact on anxiety and depression.
Another practical strategy is the 52-17 rule. Studies have found that the ideal time bracket for work is 52 minutes, followed by a 17-minute break. So not like “I’m going to switch from one browser tab to the other”, but I’m going to get up from my desk, have a snack, go for a walk, do some dancing, call a friend, and then come back! It may feel counterintuitive, but it will make you more efficient and give you more energy.
Finally, if you’ve made a list and checked off your most important tasks for the day, once those are done, you’re done. And at that point, reward yourself, watch a dumb show, or, you know, go do something fun. You have to find those spaces to do other things that recharge you.
Find out more about Dawn and her coaching and motivational speaking services at www.WholeLifeSolutions.biz or follow her on Instagram @rev.dawn or @relationshipcoachdawn . You can email her at dawn@wholelifesolutions.com.
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