From Corporate to Creative: The Honest Guide to Transitioning to Full-Time Entrepreneurship
Most of us have felt the specific weight of the "Golden Handcuffs." You have the title, the steady paycheck, the benefits, and the routine. On paper, you have "made it." But in your gut, you know you are meant to be building something of your own.
The problem is that the leap from a structured 9-5 to the wild west of creative entrepreneurship feels massive. It’s not just about the logistics of setting up an LLC or finding clients; it is about the emotional and financial rewiring required to bet on yourself.
We sat down with Ashley Mina, better known as @YourWorkWifeAshley and founder of The Working Gal Co, to break down exactly how to navigate this pivot. Ashley was laid off three years ago, a moment that forced her to jump into entrepreneurship earlier than she planned. Since then, she has built a thriving ecosystem for women who are ready to make bold pivots and build what is next.
If you are sitting at your desk right now dreaming of handing in your notice, or if you are in the messy middle of your first year solo, this guide is for you.
Listen to the full episode here: Apple Podcasts, Spotify
Watch the conversation on YouTube: Youtube
The Identity Shift Happens Before the Business Shift
When we talk about quitting a job, we usually focus on the math. Can I afford it? Do I have enough savings? But Ashley points out that the biggest hurdle is often the identity crisis that follows the resignation letter.
For years, you have introduced yourself as a "Senior Marketing Manager" or an "HR Director." That title was your armor. When you strip that away, you might feel a sense of drift.
Ashley describes this process as "grieving." You are grieving your old life and your old identity. It is common to feel like you don't know who you are without the corporate structure telling you where to be at 9:00 AM.
The "Chapter" Mindset
The most helpful way to reframe this is to stop looking for a final destination. Ashley suggests viewing your career like a book. You aren't losing your old self; you are simply adding a new chapter. The skills you learned in corporate, negotiation, project management, dealing with difficult people, are the plot points that prepared you for this current chapter.
Coaching Question: If you couldn't use your job title to introduce yourself at a dinner party, what would you say?
Start practicing that answer now. It helps bridge the gap between who you were and who you are becoming.
Signs You Are Ready to Go Full-Time
One of the most common questions before someone goes full time is, "How do I know if I'm actually ready?"
There is a misconception that you need a flawless 50-page business plan and six months of client contracts signed before you can leave. Ashley argues that the signs are much more internal.
Do you have the "Gut Instinct"?
Sometimes, the only data point you have is a persistent gut feeling that you want to do it. If the desire hasn't gone away after a few months, that is a valid business metric.
Are you "Overthinking" the work?
This sounds counterintuitive, but anxiety about the details is a good sign. If you are already stressing about what a proposal should look like, or drafting emails in your head for clients you don't have yet, it means you are mentally already in the position. You are trying to solve the problems of a business owner because you are one.
Does "Cosplaying" count as working?
Ashley mentioned that in the beginning, she often felt like she was "cosplaying" as an entrepreneur. You might sit down at your home office and feel like you are just going through the motions. That is okay. Those motions are "reps". Just like in the gym, you have to do the reps with light weights before you can lift the heavy ones. Feeling like an impostor doesn't mean you aren't ready; it means you are new. And as the saying goes, it’s not hard, it’s just new.
Financial Scrappiness: You Don’t Need to Replace Your Salary Day One
The biggest blocker for most women is the financial runway. The advice you usually hear is to save 6-12 months of expenses before you leap. While that is great if you can do it, it isn't the only way.
Ashley champions the idea of being "scrappy".
The "Bridge Job" Strategy
You do not need your creative business to pay 100% of your bills on day one. There is zero shame in taking a "bridge job" to cover your baseline expenses while you build.
Ashley knows women who run incredible online businesses but work the front desk at a Pilates studio or a barre class in the mornings. This isn't a failure; it’s a strategy. It provides reliable income, gets you out of the house, and most importantly, it takes the desperation out of your sales calls. When you aren't terrified about making rent, you can show up for your creative clients with better energy.
Where there is a woman, there is a way. If you are willing to be creative with your income streams, you can make the transition happen much faster than if you wait for the "perfect" financial moment.
Handling the "Health Insurance" Question
We can’t talk about leaving corporate without talking about benefits. For many US-based entrepreneurs, health insurance is the terrifying variable that keeps them stuck in jobs they hate.
Ashley shared a few practical ways to navigate this:
- Spousal Support: If you have a partner with a W-2, getting on their plan is the path of least resistance.
- The Marketplace: It can feel overwhelming, but there are resources specifically for entrepreneurs. Ashley recommends visiting your local Chamber of Commerce or business library (literally walk in and say hi!) to ask about local plans for small business owners.
- The Stipend Hack: This is a brilliant tip Ashley learned from working in HR. If you are contracting with larger companies or agencies, don't be afraid to ask for a "health stipend" or add a buffer to your retainer specifically for benefits. Some companies have budgets for this that go unused simply because contractors never ask.
Building a Network That Actually "Gets It"
Solopreneurship can be lonely. You go from an office full of people to just you and your laptop. If you don't intentionally build a community, you will burn out.
But networking doesn't have to feel gross. You don't need to send cold LinkedIn messages asking to "pick someone's brain."
The "Reality TV" Connection Method
Ashley’s approach to networking is refreshing: focus on the vibe, not the transaction. She has built genuine business relationships by sliding into DMs to talk about Reality TV.
When you find common ground with someone—whether it’s a show, a struggle, or a hobby—you build a real connection. Those are the people who will refer you business later, not the people you pitched cold on day one.
Find Your "Safe Space"
You need a place where you can ask the messy questions. You need people who understand why a client ghosting you ruins your whole Tuesday, or why you are stressed about tax season.
This is exactly why we built The Breakroom. We wanted a space where creative entrepreneurs could find that "water cooler" community without the corporate politics. It’s about having people in your corner who get it, so you aren't just talking to your cat all day.
Your First 100 Days Plan
If you have decided to make the jump, what should you actually do in those first three months? In corporate, you would have an onboarding plan. You need one for your own business, too.
Here is the "Ashley Mina Approved" First 100 Days Plan:
1. Create a "Brag Folder"
In corporate, you might have kept a folder of positive feedback for your performance review. Do the same thing now. Create an album on your phone or a folder on your desktop.
Screenshot every win, no matter how small. Did you update your bio? Screenshot it. Did a stranger DM you saying they loved your post? Screenshot it. Did you send an invoice? Screenshot it.
When the impostor syndrome hits—and it will—you can look back at this folder and see objective proof that you are moving forward.
2. The 3-Person Outreach Rule
Set a simple metric for yourself: Reach out to three new people every week.
The goal isn't to sell them immediately. The goal is to "shoot your shot" by saying, "Hey, I really like what you're doing. I'm new to this world and would love to connect".
This builds your confidence reps. The first time you introduce yourself as a business owner, your voice might shake. By the tenth time, you’ll say it with your chest.
3. Shorten the Gap
The "cheat code" to business growth is shortening the time between Decision and Action.
In corporate, we are trained to wait for approval, wait for the meeting, wait for the feedback. In your own business, you can decide to do something and then immediately do it. Don't sit in the misery of indecision. If you have an idea, post it. If you want to pitch a client, send the email.
Conclusion
Transitioning from corporate to creative entrepreneurship isn't about having a perfect map. It’s about being willing to write the next chapter of your life without knowing exactly how it ends.
As Ashley says, "This is my ride. Hop in or stay back".
You have the permission to build this business exactly how you want. You can be scrappy, you can be messy, and you can be successful all at the same time.
If you are ready to start writing that next chapter but want a guide to help you edit the manuscript, we would love to support you. Apply for 1:1 Coaching with us, and let’s build a sustainable business that gives you the freedom you left corporate to find.