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We’ve spent plenty of time talking about quitting, leaping, or redefining success entirely. But sometimes the smartest move isn’t to torch the ladder right away; it’s to build another one on the side.

This week, we’re diving deep into the art (and grind) of the side hustle. Because whether you’re testing a business idea, preparing for a career pivot, or just trying to feel something after a soul-numbing day job, your after-hours project might just be the bridge to something bigger.

It’s something I’ve been thinking a lot about lately. Obviously Off the Ladder itself is one of my side projects, and I’ve been exploring some others as well. Not primarily for the money (or future potential) but mainly because I like working on cool shit.

What’s inside:

• Pros and cons of the hustle

• Why there are statistically more side hustles than ever

• Delayed gratification is key

• Tools to help you get your hustle on

• Take one small step to start your side project today

Main Idea

If you spend anytime on social media these days, you’ll likely find that almost everyone has a side hustle these days. Generally, we are very pro side projects. Whether it’s to try something different, or just to make an extra buck, there are plenty of benefits to working on something outside of your day job.

What we don’t love? The pervasive need by a growing number of people to have a side hustle just to make ends meet. That’s less a meaningful project, and more a second job. Either way, it’s truly an unfortunate reality for many.

But a true side hustle, one that is by choice, that is something that you really enjoy or that is a jumping off point for something greater? That’s the sweet spot.

Working on something meaningful in your free time lets you:

• Test a new career path without risking your primary income

• Build skills and credibility before making a leap

• Reignite passion for work by doing something you chose

• Prove your idea has legs before going all-in

The flip side? Burnout is real. And if your 9-5 already eats your energy, adding a hustle can be the equivalent of strapping a treadmill to your back. The trick is to treat your side hustle like a laboratory, not another job.

Protect your time, keep your “why” in sight, and know when it’s served its purpose.

And when you are ready to take the leap, you’ll have a new set of relevant experiences, skills, and ideas, or the makings of a new business ready for your full time attention!

Ditch the Metrics

Burn the business scorecard – focus on what matters!

The Metric:
According to this 2025 Intuit article, 66% of Gen Z & Millennials (ages 18-35) have started or plan to start a side hustle. Not primarily for financial reasons, almost have were motivated to be their own boss (49%), while 42% were looking to pursue their passions.

Don’t Ditch It:
Normally we flip and dump these metrics, but not this week. We think this one is here to stay. Realizing there is a middle ground to sticking it out or completely changing careers is empowering. Having options to learn, expand, and grow beyond the traditional ladder climb is what it’s all about!

Reframe This

 A quick thought-flip to help shift how you see your work, your worth, or your path.

Old Belief: It’s not worth spending my time on it if it’s not paying the bills.

New Perspective: It’s worth it if it’s building the future I want.

Rung Breaks

A curated mix of tools, links, books, and ideas to help you step off the ladder and into your own path.

📚 Book: The $100 Startup by Chris Guillebeau – Case studies of people who built successful businesses with minimal startup capital.

🎧 Podcast: Side Hustle Pro – The Podcast – This empowering series spotlights Black women entrepreneurs who transformed side hustles into thriving businesses.

✍️ Read: “It Took Me 3 Years to Find This Side Hustle” – Honest personal story detailing the emotional journey of experimentation and growth through a Fiverr side hustle. Encouraging for anyone still searching for their stride.

Your Move

A reflection and challenge to help you break out of autopilot and make real change.

Reflection Prompt:

Challenge:

Until Next Time…

Looking to work on something that really lights you up but not ready to give up the safety of your current day job? Want something productive to spend some time on instead of doom scrolling TikTok? Ready to lay the foundation for what’s next?

Get to hustlin!

See you off the ladder.

— Sean Sirianni
Founder, Off the Ladder

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