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The Ups and Downs of a C-Level Side Hustler and the Hacks for Balancing It All

This post is part of a new series called The Side Hustle, in which we interview Millennials who are successfully redefining the 9-5. 

There are not many people who would consider the role of Chief Marketing Officer at a startup to be a “side hustle.” However, Tim Hedberg isn’t like most people.

As a master side hustler, Tim has found the key to successfully balancing his responsibilities as Video Production & Marketing Coordinator for the Institute for Humane Studies by day, and CMO of alcohol-delivery app,Klink Technologies Inc., by night. We chatted with Tim about the ups and downs of having a side hustle and some of the creative hacks he’s adopted to keep his busy life running smoothly.

Tim credits his childhood for instilling a change maker mindset in him. Growing up in countries like Venezuela and Costa Rica, where he and his siblings used to make bets on the daily inflation levels, he developed a unique perspective on global issues. After college, Tim spent some time overseas doing humanitarian work. He dabbled in entrepreneurship, but ultimately decided to try his luck as an intrapreneur at IHS, a DC-based libertarian nonprofit focused on creating a freer society through educational and career programming. He started managing their Facebook account and quickly worked his way up the food chain, from email marketing to digital media strategy. Somewhere along the way, Tim discovered a love for video production and taught himself enough to make his new passion a part of his job description.

My real passion is jumping into something I know nothing about, becoming an expert, teaching others how to become experts, and then moving on to the next challenge.

Given Tim’s passion for learning, it comes at no surprise that his side hustle originally started as a challenge. He wanted to explore freelancing to validate that his video production skills were good enough to cut it outside of the nonprofit world. His friend challenged him to make $500 in freelance earnings that year and when the founders of Klink reached out shortly afterward about a short video project, Tim  jumped on the opportunity. While he didn’t have the skill set or experience at the time, Tim was confident he could figure it out. And what began as a freelance challenge, eventually turned into his current role as Klink’s CMO.

Tim’s typical daily routine:

  • 8:30AM Wakes up
  • 9:00AM Eggs and a Yerba Matte Tea for breakfast
  • 9:30AM Drives to IHS while listening to one of his favorite podcasts (see below for more detail)
  • 10:00AM-12:00PM Answers emails, meets with the team, and interviews experts
  • 12:00PM Runs a workshop over lunch on Growth Hacking
  • 1:00PM-4:30PM Reviewing scripts, overseeing shoots, or working with an editor on the latest cuts
  • 5:00PM Gets home and uses meditation or yoga to avoid the post-work slump (he’s been trying AcroYoga)
  • 5:30PM Klink team call
  • 6:00PM-9:00PM Works on Klink to-do’s
  • 9:00PM-11:00PM Might attend an event or will meet a friend for a drink
  • 1:00AM-3:00AM Bedtime

What hacks do you use to balance your full time job and your side hustle?

  • Start the day slow: “I used to grab my phone as soon as I woke up to start responding to emails. I thought this was very efficient, but recently realized how counterproductive the habit could be. It made me more anxious. Now, I try to start the day slow and remove the illusion of urgency.”
  • Be transparent: “One of my founding principles is being overly honest.  I tell everyone everything. My boss was the first to know when I got promoted to CMO of Klink. I think it’s important to set expectations.”
  • Multi-task when possible: “Find opportunities to take on projects that benefit both your job and your side hustle at the same time. I recently produced and directed a 3-part educational series on alcohol regulation for LearnLiberty, which also helped me understand the legal territory Klink operates in. My colleagues at IHS even help with Klink projects by doing social media or writing blog posts from time to time.”
  • Meditate: “I use meditation to refocus, reprioritize, and calm down after a day in the office before switching to Klink. I have found that meditation helps me concentrate on what I want to, not what’s pushed at me. I can fully feel my body, enjoy my work, taste every bit of food, and enjoy the pleasant breeze on my face. It’s been a pleasant surprise and an important habit I’ve started to form. ”
  • Separate your inboxes: “I found it was unsustainable if I let my Klink emails distract me during the work day so I have become pretty disciplined about separating my inboxes. I make sure to only check my Klink inbox once in the morning and once during lunch at set times. This has also made me realize that most things just aren’t that urgent.”
  • Stay on your feet: “Get a standing desk.”
  • Create advocates: “Take the time to help your friends with their projects and get them to be promoters for you as well.”

Biggest drawback of being a side hustler?

“Guilt. Any time I’m socializing after work, I feel like I need to be working on Klink, but if I’m working, I feel guilty that I’m not spending time with my friends. A recent relationship actually ended because of this reason. When I started Klink, I consciously thought through these scenarios and asked myself if I would be willing to sacrifice certain things in the short term for longer-term success. The answer was yes, especially because I know that I won’t be able to make these sacrifices forever.”

Do you ever drop the ball trying to juggle so many things? 

“Occasionally there are weeks when my productivity suffers on one side or the other. Some weeks I’m consumed by a new campaign for IHS,  and then there are days like tomorrow where I have to take a day off to spend with Klink investors. I justify this internally by knowing that I make up for it in a serious way – at the end of the day, no one doubts my contribution.”

Advice for someone considering to start a side hustle?

“I’ve read many interviews with people who come across as very successful on paper; it’s only when I get to know them that I realize they’re a mess inside. It makes me feel a little better, as most of the time I have no idea what I’m doing. Before starting a side hustle, ask yourself if you honestly want to find out if this is something you can achieve; and more importantly, if you’re comfortable with the answer being no. You need to acknowledge the possibility that you might fail.”

Any desire to make your side hustle your main gig?

“Not in the short term. I’m committed to both my teams and love what I do.”

Some of the podcasts, apps, and books that Tim is using to keep up his hustle: