Employee to Entrepreneur, The Realities of Midlife Entrepreneurship

Have you been thinking about going solo because it feels like everyone’s doing it? Or maybe you’ve heard a well-meaning chorus of, “You’re so good at what you do, you should start your own thing!” I get it. The allure of being your own boss, setting your own hours, and building something with your name on it is hard to ignore. But before you dive in because it seems like the next logical step—or because everyone thinks you should—pause for a moment. Entrepreneurship isn’t a one-size-fits-all solution or a badge of superior ambition. It’s a path filled with both freedom and responsibility, and it’s only worth it if it aligns with your values, skills, and aspirations—not someone else’s expectations.

Let me share my story, because everyone seems to be wondering, what is it exactly that I do now.

2024 wasn’t the year I planned to become an entrepreneur—it was the year life decided for me. After leaving my role, I thought I’d take a few months to recalibrate, maybe even take a proper sabbatical. But life had other plans. Projects started coming my way fast—colleagues, peers, and even past clients reached out almost immediately. Suddenly, I found myself knee-deep in work before I even had the chance to properly name and brand my business.

My (Yet to be named, but awesome) Company was born in the middle of the hustle. There was no grand strategy, no website, no polished pitch deck. For months, it has just been me, working closely with my clients, delivering results, ironing out the kinks, all while figuring out the basics of building a business on the side.

The identity of my work? Let's just say, I put Business BEFORE Brand (more on that in a separate article), but the website is coming soon, I promise!

So, The Dark Side of going solo? Of course, It’s Real.

Entrepreneurship isn’t just about freedom—it’s about responsibility. For guidance counselors and university outreach pros considering the leap, your expertise will only get you halfway. The other half? Learning to sell your services, market yourself, and juggle all the operational chaos.

1. Wearing Too Many Hats As a solopreneur, you’re not just guiding students or crafting outreach strategies—you’re also handling invoicing, running social media, troubleshooting tech, and planning events. It’s empowering, but the constant juggling can leave you stretched thin.
2. Rebuilding Credibility When you step away from the backing of a well-known institution, your expertise alone isn’t enough—you now have to build trust as an independent brand. Convincing clients to invest in you takes time, effort, and a lot of strategic networking.
3. Financial Instability Imagine leaving a secure salary to launch your own counseling practice. In the beginning, your income might be sporadic—one month is great, the next feels like a drought. Without careful financial planning, reinvesting in your business while covering personal expenses can feel like walking a tightrope.
4. Long Hours When you’re the entire team, late-night client calls and weekend follow-ups with schools or universities are the norm. A counselor I know barely has time to breathe between student sessions and managing her own operations. The work doesn’t stop just because the clock says so.
5. Fear of Failure What if no students enroll in your college guidance workshop? What if that partnership with a school doesn’t pan out? These “what-ifs” can haunt you—but learning to take calculated risks is part of the growth.
6. Wearing All the Hats As an independent admissions consultant, you’re not just guiding students; you’re handling client onboarding, marketing, invoicing, and everything else. One outreach professional I know joked about becoming her own IT support just to set up Zoom sessions!
7. No Pre-Built Structure There’s no school bell ringing to tell you when to start or stop. Building a routine from scratch is liberating but requires serious discipline to stay on track and meet deadlines.
8. Continuous Learning From figuring out how to run Facebook ads for your workshops to mastering invoicing software, you’ll find yourself learning new things daily. A colleague who started her career guidance business admits she’s spent more hours on Canva than on actual counseling lately!
9. Loneliness Gone are the team meetings and lunchroom chats. Solopreneurship can feel isolating. Finding a peer group or mentor who understands your journey can make a world of difference.
10. Stress Management Balancing client demands with building a business is no small feat. One admissions consultant shared how juggling contracts with her personal life left her exhausted—but she also found purpose in every success story.

The Upsides of Small Business Startups and Solopreneurship

Let’s not forget: entrepreneurship comes with unmatched highs. The ability to design your career, pick your projects, and see your direct impact on students’ futures? That’s the kind of fulfillment you don’t find every day.

The chaos is real, but so is the magic. If you’re ready to embrace both, the journey might just be worth it.

1. Freedom to Define Success When you’re running your own show, you decide what success looks like. For a counselor, this could mean focusing solely on social impact careers or creating bespoke workshops for students—no institutional red tape to hold you back.
2. Flexibility to Adapt Want to work with schools in the mornings and spend your afternoons mentoring students one-on-one? You can. One admissions consultant I know structures her day to fit both her client calls and her yoga practice.
3. Direct Impact Every action you take has immediate results. For a solopreneur, watching students get admitted to their dream colleges or seeing schools benefit from your strategies is a reward that feels deeply personal.
4. Creative Expression Your business, your way. Whether it’s designing a one-of-a-kind career guidance program or creating a blog to share insights with parents, the freedom to innovate is exhilarating.
5. Personal Growth The challenges of solopreneurship push you out of your comfort zone. One outreach professional shared how starting his own consultancy taught him not just new skills but also resilience and confidence he never knew he had.
6. Financial Potential Your earnings are no longer capped by a fixed salary. A guidance counselor who pivoted to private consulting now earns more in a month than she used to in three—proof that hard work pays off.
7. Legacy Building This is your chance to create something bigger than yourself. A solopreneur in admissions could build a platform that revolutionizes how students prepare for applications, leaving a lasting impact on the industry.

The Real Question So, should you take the plunge? That depends. Entrepreneurship isn’t inherently better or smarter—it’s just one path. Staying in a stable, fulfilling job can be just as rewarding.

For me, entrepreneurship wasn’t a planned journey but one born from opportunity. The pace has been relentless, but the rewards are undeniable. Whether you’re considering taking the leap or staying in a role you love, remember: the grass isn’t greener on one side or the other—it’s greener where you water it.

Because here’s the truth: entrepreneurship isn’t for everyone. And that’s perfectly okay.