8 Years Self-Employed: The Questions That Built My Business
- Jess Amburgey
- May 27
- 5 min read
April 2025 marked 8 years of self-employment for me—eight years of scary decision-making, messy middle parts, and hard lessons - but a lot of wins. Shewwww...My journey didn’t start balanced or with (ANY) boundaries. I "hustled" and figured things out along the way - some from friends - mostly on my own. With time and a whole lot of personal development, I now have a rhythm.
I’ve grown my clientele, built trust with my audience, and now I’m able to say “no” to things that don’t align without guilt.
If you’ve ever thought about taking the leap into self-employment or monetizing that side gig you can’t stop thinking about, I want to share a few key questions that shaped how I do business—and why they matter.

IF YOU DON'T BELIEVE IN YOU, HOW WILL ANYONE ELSE?
Confidence isn’t a luxury when you're self-employed — it’s a necessity. If you don't trust your own skills, ideas, and values, it will be hard for others to as well. It’s about grounding into what makes you uniquely qualified to show up in your own way.
Why it matters: Belief in yourself is the foundation of your brand, your pricing, your sales, and how you move through rejection. If you KNOW your service will help someone or make their lives better, selling yourself becomes a whole lot easier.
HOW CAN PEOPLE SUPPORT YOU IF THEY DON'T WHAT YOU DO?
People can’t hire you if they don’t know what you offer. Your followers want to cheer you on, book your services, buy your products, and share your business with others… but they’re not mind readers! If they don’t know what you offer or how you can help them, how can they ever show up for you?
Why it matters: There’s someone out there right now who needs exactly what you offer — but they won’t know it if you keep staying quiet.
IF YOU DON'T TELL PEOPLE HOW TO PAY YOU, HOW WILL YOU MAKE MONEY?
You’d be surprised how many creatives and service providers don’t make it easy to buy from them. Make sure your payment process is clear, accessible, and aligned with your values.
Why it matters: Money can flow more freely when the logistics aren’t a mystery. Make it easy for people to say “yes” to working with you and make it easy for yourself to receive.
IF YOU DON'T SET BOUNDARIES, HOW WILL CLIENTS KNOW HOW TO TREAT YOU?
In my early years, I said yes to everything and ended up burnt out and underpaid. But that was MY fault. How can a client respect my workflow, if I don't tell them what it is?
Why it matters: Boundaries are a blueprint for mutual respect, build better relationships with your clients, protect your energy, and allow you to deliver your best work.
IF YOU DON'T INVEST IN YOUR GROWTH, HOW WILL YOUR BUSINESS EVOLVE?
Investing in coaching, education, or even software can fast-track your progress and help you work smarter and quicker. Your levels of investment can vary over time depending on your needs.
Why it matters: Growth doesn’t just happen—it’s intentionally built.
IF YOU DON'T NETWORK, HOW WILL YOU EXPAND YOUR OPPORTUNITIES?
Connections have been a huge party of my growth. Some of my best gigs came from casual conversations, DMs, and referrals. This doesn't always mean going to awkward networking events (but those can always be beneficial), networking can happen anywhere, anytime. When you believe in your offers, you can fit them into everyday conversations.
Why it matters: Community creates momentum. If someone is talking about a need they have and it's something you can assist with, tell them.
IF YOU DON'T PRIORITIZE SELF-CARE, HOW WILL YOU SUSTAIN YOUR ENERGY AND PASSION?
Self-employment isn’t just about freedom—it’s about responsibility. You are your greatest resource, and burnout doesn’t serve anyone. My version of self-care ranges from couch-rotting days or closing the laptop at 3PM for early happy hour. But I had to build the processes and boundaries with work/clients to give myself the freedom to do those things.
Why it matters: You didn’t leave a 9–5 to recreate hustle culture in your own life. Rest is part of the plan.
IF YOU DON'T CELEBRATE YOUR SUCCESSES, HOW WILL YOU STAY MOTIVATED?
We’re so good at moving the goalpost once we've hit a milestone. But it’s important to pause and celebrate that launch or project and how far you’ve come. Eight years?! You better believe I’m celebrating.
Why it matters: Wins remind you why you started—and keep you going when things feel hard.
IF YOU DON'T WORK HARD AT THE BEGINNING, HOW WILL YOU SET YOURSELF UP LATER?
Unfortunately, there's usually not a shortcut in the beginning. You’ve got to be willing to dig in, test, pivot, and build your reputation. But that hard work pays off in sustainability and freedom down the road.
Why it matters: The hustle phase is real—but it should be a season, not your forever. It's hard not to look at some of the seasoned people in your industry and want to snap your fingers to end up there, but they put in the work just like me, and just like you will.
IF YOU DON'T OWN YOUR STORY, HOW WILL YOU CONNECT WITH YOUR AUDIENCE?
The messy parts. The pivots. The moments that shaped you. That’s the stuff people relate to. Vulnerability and authenticity aren’t marketing techniques—it builds real trust and connection.
Why it matters: People don’t buy from perfect—they buy from real. Owning your story builds community, not just a customer base. Your truth is your greatest tool.
IF YOU DON'T GIVE YOURSELF PERMISSION, WHO WILL?
We wait for credentials, external validation, or for someone else to label us as “ready.” But here’s the thing: that day might never come. You are the gatekeeper of your next move. Just say YES to trying something new - figure the details out later.
Why it matters: Waiting for permission keeps you stuck. Giving yourself the green light is the first step to stepping into your power and creating impact. You only have to be 1-2 steps ahead of someone to help them!
IF YOU DON'T ALLOW YOURSELF TO EVOLVE, HOW WILL YOU STAY IN ALIGNMENT?
You’re not supposed to stay the same. What served you last year might not fit anymore—and that’s okay. Your interests, passions, and goals will change. Let your brand and business reflect that growth. I used to photograph weddings and offer logo design services. Now I focus more on social media management, other forms of photography, coaching, and public speaking. Just because you start something doesn't mean you have to do it forever!
Why it matters: Staying static out of fear keeps you out of integrity. Evolution keeps your work honest, your message relevant, and your energy aligned.
IF YOU DON'T DEFINE SUCCESS FOR YOURSELF, HOW WILL YOU KNOW WHEN YOU'VE ARRIVED?
So many people are chasing someone else’s version of success—more money, more followers, a bigger house, a busier calendar. But if you don’t stop and ask yourself what you actually want, how will you know when you’ve made it?
Why it matters: When you define success on your own terms, you create a life and business that’s sustainable, satisfying, and actually worth celebrating.
Now I leave you with one final question - WHAT'S STOPPING YOU?
Fear of the unknown was stopping me. I didn't even know how to make an invoice when I became self-employed. I wish I had someone in my corner to support and cheer me on. If that sounds like something that would be beneficial in your journey, I would love to be your hype gal!
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