Career Advice

Starting a side hustle while working at a full-time day job you’re dreaming of quitting

BootstrappingMindsetSolo Founders
39 calls booked about this topic

Facing a similar challenge?

  • Talk to someone who has been there before
  • Get unbiased insight from industry veterans
  • Work through the issue with a mentor by your side

Here’s why you’re might be thinking of quitting your “day job” to focus on building a startup:

  • You don’t like other people telling you what to do
  • You want control over your time and lifestyle
  • You want to create an impact that’s congruent with your core values
  • You know you can do it if you apply yourself fully

All great reasons to take the plunge.

But for goodness sake, baby steps, please!

Before making any drastic decisions that you might regret, test the waters by creating a side hustle.

Creating a side hustle is a great way to validate that you can pull it off.

If you’ve been a full time employee for a few years, you’re probably not used to the lack of constraints of the entrepreneurial lifestyle. This means you’ll have a tough time figuring out a niche for yourself. Too much choice!

Plus, adding a day job into the mix can get you feeling discouraged and uncertain about the strategies and direction you should take.

You might even have some mixed feelings about starting a side hustle. Thoughts like, “is this just a distraction from reality?” are common and the answers are nuanced depending on your personal situation.

If you want to be your own boss and are hoping to get guidance to steer you in the right direction, talk to someone who’s “been there done that,” preferably outside your circle of peers.

Kosta Panagoulias

Founder at
My company is 100% revenue-financed. Meaning we started with zero dollars in the bank, and never taken a dime from anyone. Maintaining a lean and disciplined ideology is what helped our company grow to +7-figures in annual recurring revenue.

Kosta is friendly, patient, and understood our marketing goals for our new Saas. He offered a unique approach to get the word out about it – traditional sales – which I thought was brilliant. He had valid ideas and mentioned some data to look into that approach. He was very easy to talk with and said I could reach out whenever to share our progress. If you get the chance to bounce ideas around with him, I recommend it. 

Kirk Deis
CEO and Co-founder at Treehouse

On point!
When asked ‘What would you do if you were in my situation’, Kosta had extremely solid advance, particularly understanding the bootstrapping situation. 
A pleasure to talk to and get specific actionable next step advice!

Paul Prudden
Founder at Amazing Author Ads

David Kelly

General Manager at AppSumo Originals
My FAVORITE way to build a business is from $0. Having no marketing or growth budget might seem like a problem... but it really just requires more creative solutions to grow. And here's a secret: Many of these "secret" free marketing channels are more sustainable than paid platforms, which is subject to the paid platform's latest whim (looking at you, Facebook Ads).

“David was absolutely awesome! Super personable and very cool guy. Very knowledgable and really understood our business and it was relatable content for what we need and what we needed to hear. Considering we are early stage, his advice and growth strategies we can actually implement which is great. It’s also awesome just to be reminded that he also was at the same stage we were at first too! Will certainly be having more calls with him in the not to distant future! Can’t recommend him highly enough :)”

Dan Siepen
Head of Growth and Marketing at Wellshare

“The best spent hour of the day and probably of the week. Trevor gave a lot of precise and actionable tips on SEO & content marketing, that helped me come with a more defined strategy. We discussed tons of different growth & monetization ideas, as well, which I’ll be putting into practice soon.”

Rich Clominson
Founder at