7 Unexpected Benefits of Freelancing
Why I’m motivated to make this a lifelong career
The expected benefits are why people start freelancing:
The time freedom.
The location freedom.
The opportunities for higher income.
But freelancing has a much greater impact than these surface-level tangibles. It changes our relationship to “work.” And ourselves.
#1: It puts you in the driver’s seat
Freelancing puts all the decisions back in your hands (not the company’s):
→ how will you spend your time?
→ what goals are really worth striving for?
→ which activities actually move the needle?
As an employee, your day is shaped by someone else’s agenda. Freelancing flips that.
When you’re no longer working through a to-do list that’s been assigned to you, you’re forced to decide what matters for yourself.
And how you choose to spend your time is a signal:
This is what I care about. This is where I’m headed.
#2: You learn more deeply about yourself
Freelancing forces you to set your own goals, which means asking: what do I really want?
Surprisingly, that answer doesn’t come that easily for most of us (me).
You’re no longer working off someone else’s expectations or company objectives – you have to know yourself well enough to create your own. That means paying close attention:
What energizes me vs. drains me?
What do I actually care about vs. just pretend to?
What am I really trying to build here?
That’s why I think freelancing can be a sneaky spiritual path. It doesn’t have to be – but if you let it, it forces you to confront who you are, what you want, and what kind of daily life you’d love to build for yourself.
#3: It adds intrinsic motivation
When working for a company, I’ve only felt truly motivated for so long before it feels like I’m lying to myself.
Freelancing changes that: income is directly tied to your effort. And that need to pay the bills is motivating in itself.
But it also taps into something deeper: the urge to create.
Psychiatrist Paul Conti calls this our generative drive – the desire to create and contribue to the world in a meaningful way. He calls it a core feature of mental health, linked to a sense of agency, gratitude, peace, contentment, and delight.
Freelancing gives me this outlet for creation.
Instead of following someone else’s playbook, you get to experiment, add your weird touches, and create in ways only you can.
#4: You gain a sense of agency
In my short 5-year career, I’ve had three separate occasions where I’ve built my income from zero to sufficient (to live & pay rent in a major city) in less than 60 days.
→ In 2020, when I took freelancing projects immediately after graduating college (COVID year, no jobs).
→ In 2022, when I was laid off after my short stint working at SelfDecode (they grew their team too quickly, and our marketing department was first to go).
→ In 2025, when I decided to restructure my business in a way that would give me more agency (instead of contracting gigs with hourly rates).
This gives me an incredible sense of agency over my life and confidence I wouldn’t have if I only relied on outside factors to pay my rent.
#5: It can be more fun
Derek Sivers writes: “When you make a business, you get to make a little universe where you control all the laws. This is your utopia.”
Building a freelance business means you can build it however you want…
> Work with the people you love to work with.
> Find the intersection of your work & your interests.
> Experiment with weird, fun ideas.
> Structure your day around things that energize you.
For me, that may mean a mid-day hike some days. Or working on a personal creative project before diving into client work.
But it’s something I have to remind myself often: You have the power to make this enjoyable.
#6: You’re forced to fail
Failing as a freelancer is both inevitable and valuable. Not failing is a sign you’re playing it safe.
Most “failures” aren’t catastrophic, though it may feel like it. It’s all data to help you refine your process.
Every “no”...
Every botched client call…
Every offer that flopped…
Reveals something specific you can improve. It’s a process of iterating toward something that genuinely works… both for you and for the market.
And if you’ve never misstepped, that may be a sign you’re walking a road that’s too smooth to lead somewhere new.
#7: It makes your market value clear
Freelancing forces you to face the truth about your market value. You only get paid when you deliver something people truly want.
Another great Derek Sivers quote:
“Money is nothing more than a neutral exchange of value. If people give you money, it’s proof that you’re giving them something valuable in return.”
As an employee, it’s easy to believe a paycheck comes just for showing up. Freelancing kills that illusion fast.
You’re not “getting” a job, you’re making a contribution. And the market decides what it’s worth.
That shift changes everything. You start asking:
What unique skills do I bring?
What real, concrete impact does my work have?
Where does my value align with what people will pay most for?
Freelancing teaches you that you’re not just trading hours for dollars, you’re trading value for value.
Closing thoughts
Freelancing doesn’t have to be this transformative journey. It can just be a way to make money without a boss breathing down your neck.
But if you let it, freelancing can become much more:
> A mirror that shows you who you really are.
> A test lab where failure turns into growth.
> A practice ground for building a life on your own terms.
At its best, freelancing is a path toward self-knowledge and intentional living.