Why I Paused Entrepreneurship for a 9-to-5 (and How It’s Making Me a Better CEO)
- Cole Woods
- Sep 2
- 9 min read
For the first 30 years of my life, I was collecting lives the way some people collect stamps. Professional athlete? Check. International runway model? Check. Software Developer? Check. Beauty tech consultant? Check. My career path has been more of a plot twist than a straight line.
So when I decided, by choice, to step into a more “regular” 9-to-5, it wasn’t because I had run out of steam on my dreams. Quite the opposite. In my mid-30s, I’ve developed a whole new appreciation for the tangible and intangible benefits that come with a well-chosen corporate role.
When I took a step back from full-time entrepreneurship, I didn’t stop moving; I pivoted. From tech to business strategy to finance, each chapter has added another layer to my perspective. These shifts aren’t random detours; they’re grooming me to step fully into my role as a CEO.
Everyone’s path looks different, but as a Mental Projector with Desire Motivation, my success has always hinged on two things: seeing the vision clearly and outlining an actionable plan to bring it to life. That’s why my current role as a Strategic Communications Consultant at one of the top investment firms in the world isn’t just a job, it’s part of the blueprint.
The job I have now? It supports my ambitions, my lifestyle, and my long game. It’s not a detour, it’s a strategy. And if you’re an entrepreneur thinking about making a similar move, you can make it a power play, too.
But here’s the key: your 9-to-5 must serve at least three core purposes.
1. Stability & Peace of Mind
When you’re an entrepreneur, the hustle can be glamorous… until it’s not. I’ve had months where my inbox was full of opportunities and my calendar full of client calls. I’ve also had months where I stared at my bank account like it had personally betrayed me.
That’s where the right 9-to-5 steps in. It’s not just about the paycheck; it’s about creating a baseline of stability that frees up your brain to dream bigger, think clearer, and execute smarter.
And that stability? It comes with perks that, in your 20s, you might have glossed over, but in your 30s? Baby, you feel them.
Health & Dental Insurance
Not sexy, but necessary. One ER visit without insurance can wipe out your runway for the next big business move. But beyond emergencies, having access to healthcare means you can finally shift from being reactive to proactive about your well-being.
With the right coverage, you can schedule annual checkups, full workups, and screenings that help you understand your body on a deeper level before issues turn into problems. Preventative care means more energy, fewer sick days, and the clarity to focus on your goals.
And specialized care? That’s the glow-up no one talks about. Dermatology visits, a session with a dietician, or even mental health services are often covered or discounted through your plan. That’s not just healthcare, it’s self-care that elevates your quality of life across the board.
Sign-On Bonuses
A sign-on bonus isn’t just a nice-to-have; it can be a powerful piece of your financial strategy. Whether you use it to pay down debt, boost your savings, or invest directly into your next business venture, that upfront lump sum creates breathing room. It’s money you didn’t have to wait months to accumulate. When leveraged intentionally, a sign-on bonus can serve as seed capital for your entrepreneurial goals, a cushion for emergencies, or even a wellness investment to give you a stronger foundation moving forward.
Relocation Packages
Starting fresh in a new city can be overwhelming and expensive. Relocation packages change the game. From covering moving expenses and temporary housing to travel stipends and realtor assistance, the right package makes it easier to embrace opportunities that would otherwise feel out of reach. Beyond logistics, relocation often places you in environments that expand your network and expose you to new markets, mentors, and inspiration. It’s not just about moving, it’s about strategically positioning yourself in spaces that align with your growth.
Flexible Spending Accounts (FSA) & Health Savings Accounts (HSA)
Tax savings + covered care = more money and more peace.
Wellness Stipends
One of the perks of modern workplaces is that many of them offer wellness stipends, funds you can use toward gym memberships, therapy, meditation apps, ergonomic chairs, or even a massage after a stressful quarter. This isn’t just about perks, it’s about sustainability. When your employer invests in your well-being, you’re better equipped to bring your full self to both your job and your own business. It’s essentially free money for habits and practices that keep you energized and resilient.
Retirement Contributions
It’s easy to put retirement on the back burner when you’re an entrepreneur because you’re so focused on the now. But the truth is, securing your financial future makes you a sharper decision-maker today. Many employers not only provide retirement plans like 401(k)s, but also match your contributions. That’s literally free money compounding in your name, year after year.
Think of it this way: the retirement contributions you stack now give your future self permission to take bigger risks, bolder pivots, and even early retirement if you choose. That’s freedom. And as an entrepreneur, freedom is the whole point.
2. Investment in Your Development
If stability keeps you steady, development is what keeps you sharp. One of the biggest misconceptions about taking a corporate job is that you’re somehow “settling.” Truth is, the right role can act as a fully funded accelerator for your growth, without you needing to apply for grants or pitch to investors.
Formal Education (On the Company’s Dime)
College courses. Certifications. Executive training programs. Industry conferences. Many companies have education reimbursement or sponsorship programs that will pay (yes, pay) for you to learn. That means you can stack degrees, certificates, and credentials while still collecting a paycheck.
When I was in my 20s, I thought going back to school meant I had to put everything else on hold. Now? I know better. If your employer is willing to cover the tab for an Ivy League course, a specialized certification, or even a conference in another city, you’d better believe that’s an investment in my business’s future disguised as “employee development.”
On-the-Job Experience
There are skills you just can’t get from YouTube tutorials or weekend workshops. The day-to-day realities of a well-run company (systems, processes, compliance, leadership dynamics) are a masterclass in operational excellence.
Every meeting you sit in, every project you manage, every problem you solve is building a toolkit you can carry right back into your own venture. And because you’re learning on someone else’s budget and infrastructure, the stakes are lower while the lessons are still high-value.
Cross-Functional Exposure
Entrepreneurs wear a lot of hats, and so do high-performing employees. Working across departments (marketing, operations, finance, HR) gives you an insider’s view of how every part of a business connects. That knowledge becomes your superpower when you’re back at the helm of your own venture.
Travel Opportunities
From conferences to client visits, business travel is a double win. You’re building professional relationships and getting market research in real time. You never know when a trip for work could spark your next big idea.
And if you play it right? These trips can also double as content and marketing for your own brand. From documenting behind-the-scenes moments to sharing your insights from panels, workshops, or even the destinations themselves, business travel gives you built-in opportunities to showcase your expertise and lifestyle. It’s not just a trip, it’s a stage. With the right strategy, every flight, event, or meeting becomes another piece of visibility and connection for your personal brand.
Access to Tools & Technology
Think enterprise-level project management software, premium CRM platforms, advanced analytics dashboards, the kind of tools that can cost thousands if you were footing the bill yourself. At a 9-to-5, you get hands-on training with these systems for free. That’s professional development you couldn’t buy more efficiently if you tried.
But here’s where it gets even more powerful: you can leverage that experience to elevate your personal brand. By understanding how to navigate and optimize these tools, you position yourself as someone who not only does the work but also knows the systems behind the work. Sharing insights, tips, or even just your comfort with advanced platforms shows authority and makes your consulting (or your next business venture) instantly more credible.
Instead of saying, “I’m familiar with operations”, you can confidently say, “I’ve worked with the same enterprise tools Fortune 500 companies use to scale.” That’s the kind of subtle authority that sets you apart.
3. Quality Connections & Relationships
One of the most underrated benefits of the right 9-to-5? The people.
In my earlier entrepreneurial years, my network was almost entirely made up of fellow creatives, brand founders, and industry peers. That’s great, but it’s also a bit of an echo chamber. Now, in my corporate role, I’m sitting in rooms with executives, decision-makers, and people whose expertise is miles away from mine. That diversity of thought is priceless.
These aren’t just LinkedIn connections, they’re real relationships with people who have the influence, insight, and reach to open doors. Sometimes those doors lead to partnerships, other times to opportunities you didn’t even know you wanted.
Mentorship & Sponsorship
Many companies offer formal mentorship programs, but even if they don’t, being in proximity to high-caliber talent creates organic opportunities to learn. And let’s be clear, mentorship is great, but sponsorship is gold. You want the kind of relationship where someone not only advises you but also advocates for you in rooms you’re not in.
Access to Key Decision-Makers
If you’re strategic, your job can place you shoulder-to-shoulder with people you might have paid thousands to hear speak at a conference. You get to have actual conversations, ask smart questions, and plant seeds for future collaborations.
A Network That Travels With You
The relationships you build in the corporate world don’t disappear when you hand in your resignation. Those people can become clients, investors, collaborators, or even your biggest champions when you launch your next venture.
The Entrepreneurial Edge in Corporate Spaces
Here’s the part nobody talks about: coming from entrepreneurship actually gives you a leg up. Suppose you know how to properly frame and bolster your entrepreneurial experience on your resume. In that case, you can position yourself for roles that are above entry level, roles with higher pay, more influence, and greater access.
Running your own business forces you to become adaptable, resourceful, and solution-oriented. These are exactly the qualities companies want in leadership and strategic positions. You just have to present them in a way that translates to corporate priorities.
“Sometimes the path forward doesn’t look the way you imagined it. The smartest move you can make is being open to a different route, one that still leads exactly where you’re meant to be.”
How I’m Living This Strategy Right Now
Today, I am a Strategic Consultant to women, brands, and organizations. In the past, I’ve worked with clients across various industries, including the creative, fashion, sports, and beauty industries. But working closely with beauty founders taught me something powerful: business success often comes down to two things: funding and access.
To become the best consultant and trusted advisor to the people I serve, I knew I needed to expand my repertoire in finance. My overarching goal is not only to guide my clients toward success but to one day invest in the businesses I truly believe in.
And so, I recently accepted a role as a Strategic Communications Consultant at one of the top investment firms in the world. This move adds a globally recognized name to my resume, builds my financial acumen, and yes, checks every single box I’ve outlined in this post: stability, development, and connections.
You might be wondering how I’m able to pivot so seamlessly across such diverse industries. The answer is intention and strategic positioning. And I can show you how to do the same in a way that makes sense for you.
Ready to Make Your Move?
Taking a 9-to-5 isn’t about abandoning your entrepreneurial dreams; it’s about fueling them. The right role can give you the stability to plan, the skills to execute, and the connections to scale.
At Beauty, Brain & Brawn Consulting Agency, I specialize in helping women plan and execute lifestyle shifts toward living their softest life. I create a unique curriculum tailored to your goals, one that focuses on the foundational structure of your desires, getting clear on your “why,” and mapping your path forward with actionable steps.
If you’re ready to make a strategic career move, elevate your lifestyle, and design the life you’ve been craving, let’s talk.
Schedule your consultation today and let’s start building your next chapter.
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This information is so helpful. It made me realize the benefits of strategic movement. I love it.💯