You know those moments when you’re balancing so many things that you think, Man, when did life get so hectic? That’s where Will Tarashuk found himself. But unlike most of us who dream of quitting the 9-to-5 and diving headfirst into entrepreneurship, Will took a different approach. Instead of throwing everything away for a side hustle, he decided to keep his job while building his business on the side. It’s not flashy, and it’s not some overnight success story. It’s slow, steady, and honest—exactly the kind of story you don’t hear enough about.
Will didn’t just wake up one day and decide to be an entrepreneur. It was more like he stumbled into it, realized he was onto something, and then built it up, brick by brick. His journey is a refreshing reminder that you don’t have to go all in and risk it all to make your entrepreneurial dreams come true. Let’s dig into the two biggest lessons I took away from my chat with Will.
Balancing a Job and a Side Hustle Without Losing Your Mind
Will didn’t sugarcoat it—balancing a full-time job and running a business is no joke. But he’s figured out a way to make it work. And the key? Time management and setting boundaries.
“I’ve got my 9-to-5 that covers my basics, and the side hustle gives me that extra income. I’m not looking to go full-time with the business, at least not right now,” Will shared. He’s not in a rush to leave his stable job. In fact, he’s pretty content balancing the two. For him, entrepreneurship is more about supplementing his life, not completely taking it over.
Will schedules his time meticulously. “Monday, Tuesday, and Friday are for the business. Wednesday and Thursday? Those are for the 9-to-5,” he explained. It’s a structure that lets him focus on both without letting one slip through the cracks. And the best part? He’s upfront about it. His employer knows about his side hustle, and they respect that he has boundaries.
Key Takeaways from Our Discussion:
- Set Boundaries: If you’re juggling both, set clear workdays for each. Don’t let one bleed into the other.
- Keep Your Job—If It Works for You: You don’t need to quit your job to be an entrepreneur. Side hustles can stay side hustles.
- Be Transparent: Will’s employer knows about his side hustle, and that’s created an environment of trust. If they’re aware, they’re less likely to feel blindsided.
Failure Isn’t the End: It’s the Start of Something Better
Now, here’s where Will’s story gets interesting. His first business idea? A complete flop. But instead of letting that knock him out, he used it as a learning experience.
“I was trying to do too much too soon,” he admitted. His first company, Ambiguous Podcast Solutions, was a mess. He and his partners dove headfirst into paperwork and complicated business structures without first building a solid client base. They focused more on the “endgame” than on just getting things off the ground. But he learned from it.
“It was a failure, no doubt. But that failure taught me I’m better off running the show myself,” Will reflected. His second attempt at business, Willy T Productions, wasn’t even his idea. It came from his first client. That’s right—his business model came directly from someone asking, Hey, can you help me with this?

What I Learned from His Experience:
- Failures Teach You More Than Successes: Will’s first company didn’t make it, but that failure laid the groundwork for what he’s doing now.
- Listen to Your Clients: Will’s current business came from listening to what his client needed, not what he initially thought they wanted.
- Start Small: Don’t overcomplicate things in the beginning. Build a client base before worrying about all the business formalities.
Reflections from the Interview
Reflecting on my chat with Will, it’s clear that his approach to entrepreneurship is both practical and refreshing. He’s not caught up in the idea that you need to quit your job and go all in to make it work. Instead, he’s finding ways to balance his passion with his reality. That’s something we don’t hear enough of in the hustle culture that’s often glorified.
Will’s journey reminded me that success doesn’t always mean you’re working 24/7 on your business. Sometimes, success is about finding harmony between what you need to do (your job) and what you love to do (your business). It’s about patience, persistence, and knowing when to pivot.
Here’s What I’m Taking Away:
- Patience is Underrated: Will’s been building his business slowly, and he’s fine with that. There’s no rush.
- Consistency Over Hustle: You don’t need to be working every hour of the day to grow a business. Consistent effort is what counts.
- Failures Are Just Part of the Process: Will wasn’t afraid to share his failures. It’s a reminder that failing is part of the journey, not the end of it.
- Be Open to New Ideas: Will’s best business idea didn’t come from him—it came from his client. Always be open to what the market is telling you.
- You Can Do Both: It’s okay to keep your day job while building your dream. You don’t have to choose one over the other.
Final Thoughts
Talking to Will made me realize that there’s no “right” way to be an entrepreneur. Some of us will quit our jobs and dive in headfirst, while others will balance both until the side hustle grows. Either way, what matters is that you’re building something that works for you.
If you’re trying to figure out if entrepreneurship is for you, remember this: you don’t have to rush. Take your time, learn from your failures, and always be open to pivoting when needed. Will’s story proves that slow and steady can still get you to the finish line.
CONNECT WITH WILL TARASHUK:
Website: https://www.willytproductions.com/