Front of the Check exists for one reason: to help experienced professionals claim ownership over their income and their future. The employer/employee contract is broken. Admit it. Prep for it. Do something.

"Little changes cost you. Big changes benefit you by changing the game, but only if you go first".
―Seth Godin

Turn it into a real business.

There’s a moment every side hustler hits, usually somewhere between their third Venmo payment and their first repeat customer, when the question stops being “Can I make money doing this?” and starts becoming “What am I actually building?”

That moment is where amateurs stall and professionals emerge.

Let’s be clear: side hustles are not the problem. In fact, they’re one of the most powerful on-ramps to economic independence we’ve ever seen. The problem is staying in side-hustle mode too long, operating informally, underpricing your value, and leaving leverage on the table.

If you’re over 50, this matters even more. You don’t have time to “dabble” for five years. You need traction, structure, and income that compounds.

Here’s how you make your side hustle a real business.

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1. Stop Thinking Like a Gig Worker

Most people approach their side hustle like a task list:

Do the work → Get paid → Repeat.

That is not a business. That is a job with no benefits.

A real business does three things:

A personal story. I was one of the first Nashville Lyft and Uber Rideshare drivers in 2014. They were competing head to head for drivers. Uber was playing hardball and offering a $500 bounty for drivers who came from Lyft. They were also offering incentives to drivers to make the move. As soon as the referred driver had their first Uber rideshare and the review was acceptable, the referral was triggered.

I started running Facebook ads for drivers in various cities and made $7000 that year in referrals. I leveraged systems made available to me as a driver to make money without using my time to do it. Most platforms have this kind of referral tool in place.
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2. Validate Before You Formalize

Before you run out and print business cards or build a website, ask this important question:

Will people pay for my work consistently?

Not once. Not as a favor. Not because you are helping out. Consistency is the signal.

If you have sold your service five to ten times, have at least two repeat customers, and have been referred without asking, you are not testing anymore. You are validating.

Now it is time to build.
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3. Put a Structure Around It

This is where most people hesitate and where the biggest gains are made.

Turning your side hustle into a business does not mean overcomplicating things. It means protecting yourself and creating credibility. At a minimum, do the following:

This is not bureaucracy. This is leverage. Because the moment you formalize, three things happen:

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4. Price Like a Professional

Here's the reality. Most side hustlers are dramatically undercharging.

Why? Because they are pricing based on what feels fair.

What they used to earn hourly holds too much power in their head.

They fear losing the sale.

Professionals price based on value delivered. If you are solving a $500 problem, charging $50 is not humble. It is irrational.

Raising your prices does two things.

Better clients are the gateway to a better business. I know a rideshare driver in Nashville who picked up a friend of mine for a trip to a concert one night. He handed my friend a card and said, “If you ever need a private, pre-arranged pickup, keep this card.”

Little did he know my friend works in the music business, where entertaining people out on the town is a regular part of his life. That driver now gets consistent bookings at premium prices because my friend has a reliable professional on speed dial.

5. Build Simple Systems

You do not need a tech stack that looks like a Silicon Valley startup.

You need a consistent way to get customers, a repeatable way to deliver your service, and a simple way to get paid.

That is it.

Think in terms of templates instead of reinvention, checklists instead of memory, and processes instead of chaos.

Example: A freelance bookkeeper creates one intake form for all new clients, uses a standard monthly reporting template, and sends invoices automatically on the first of each month. No reinventing the wheel. No chasing payments.

Systems are what allow you to grow without burning out.

6. Shift From Income to Asset

This is where most people never go, and why they stay stuck.

If your business depends entirely on your time, you have created a ceiling.

To break through it, start asking:

This is how income turns into enterprise.
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7. Play the Long Game (But Act Fast)

There is a paradox. You need urgency in execution and patience in results.

The winners are not more talented. They are just steady. They keep showing up. They make small improvements. They do not disappear when momentum slows.

For someone over 50, this is actually good news. You already have credibility, relationships, and real-world experience. That shortens the runway. What you need is structure and consistent execution, not genius or hustle theatrics.

In simple terms:

Final Thought

A side hustle is a great start. But it’s not the destination.

The goal isn’t to stay busy, it’s to build something that works for you.

Because the difference between earning extra money and creating real income isn’t talent.

It’s making it official.

For readers who want some structure around this move, Over50Pros offers a free course on Turning Your Side Hustle into a Real Business. Click here for the free course!

A CONVERSATION WITH RUTH SMITH

Ruth Smith has reinvented herself more than once and she'll be the first to tell you that's exactly what makes her good at what she does.

After 30+ years building teams, launching companies, and leading engineering organizations in the defense and tech sectors, Ruth walked away from the executive track to do something she found more meaningful: help other senior leaders figure out what's next. In 2023, she launched Ruth Smith Coaching, and she hasn't looked back.

Her clients are mid-to-senior tech professionals facing the moments nobody puts on a LinkedIn post: the layoff, the burnout, the slow realization that the role they've climbed toward no longer fits the life they want. Ruth coaches them through it all, from job search strategy and personal branding to negotiating the offer with confidence.

She brings something most coaches can't: she's sat in the hiring manager's chair. She knows what the room actually looks like, and she'll tell you the truth about it.

When she's not coaching, Ruth is thrifting, renovating something, or out on the lake. She's a wife, a mom to two early-career engineers, and by her own description, an encourager above all else.

Q: You've reinvented yourself multiple times—from Director of Technical Services to startup founder to SVP to career coach. What was the pivotal moment that made you realize it was time to pivot from leading engineering teams to coaching other leaders through their own transitions?

A: Losing my job was the first real disruption in my career. Until then, I had always been pulled forward into new roles. I had never had to actively look for work. When I suddenly found myself back on LinkedIn after years away, I was shocked by how much it had changed. It wasn’t just a job board anymore. People were building brands, sharing ideas, and creating their own paths.

Despite having hired more than a thousand people and led engineering teams for years, I felt like I was starting over in a system with new rules. It was humbling. At the same time, I realized I had been preparing for this moment without knowing it. I had led a career transition group during the 2009 recession and had mentored people throughout my career.

A close friend finally said to me, “If you helped others the way you’ve helped me, you’d have a line out your door.” That stuck with me. I started writing on LinkedIn, one post at a time, and began coaching on the side. It grew naturally from there.

Looking back, every major pivot in my career has come from either an unexpected opportunity or a sense that it was time for a new challenge. Coaching was no different. It just felt like the right next chapter.

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Q: After 30+ years in tech, you've sat on both sides of the hiring table. What's the biggest misconception senior professionals over 50 have about their marketability, and how do you help them reframe that narrative?

A: After more than 30 years in tech, one thing has always been true: what you know today will be outdated sooner than you expect. That pace has only accelerated with AI. Yet many professionals over 50 still believe their experience will speak for itself. It won’t.

A common mistake is relying on titles and long lists of job duties. Hiring managers aren’t impressed by what you were responsible for; they care about what you actually delivered. Did you improve performance? Increase revenue? Reduce costs? Save time? Support strategic goals? That’s what matters, and it needs to be clearly reflected on your résumé and in your interviews.

Another misconception is assuming that strong technical or leadership skills automatically translate into strong interviewing. They don’t. Interviewing is its own skill, and it needs to be practiced. Employers also want to see that you can work effectively across generations and adapt to new ways of working.

I help my clients reframe their story around impact and relevance. We build résumés that show measurable results and develop clear, compelling examples they can use in interviews. When you can tell specific stories that show how you’ve solved problems and driven results, age is no longer the focus; your results are.

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Q: You openly list "Mom to two early-career engineers" as one of the titles you proudly answer to. How has watching your own children navigate their early tech careers influenced the way you coach seasoned professionals navigating their next chapters?

A: Watching my sons start their careers has given me a real-time view of how quickly the job market changes. Our oldest graduated in 2022 and had strong opportunities right away. Our youngest graduated in 2024 and had to work much harder to land his first role. Seeing that contrast firsthand reinforced how unpredictable and competitive the market has become.

Both of my kids are independent and determined to find their own way. Like most young professionals, they usually think they’ve got it handled until they don’t. I still remember the day one of my sons called me twice during my workday. When I finally stepped out of a meeting, I asked if everything was okay. He said, “Yes, but I have an offer, and I need your help. Should I negotiate?” We talked it through, and 30 minutes later, he called back to say it was the most successful negotiation of his career so far.

They also challenge me in the best way. They point out outdated leadership assumptions, share how their generation approaches work, and talk openly about the pressures they face. Over time, their friends and even other parents started reaching out to me for advice, which reinforced how transferable this guidance really is.

Staying close to their experiences keeps me current, curious, and relevant. It reminds me that every generation brings new motivators, new tools, and new ways of solving problems. That perspective helps me coach seasoned professionals with empathy and a clear understanding of where the workforce is headed, not where it used to be.

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Q: Many of your clients are navigating career transitions after layoffs or burnout. What's the toughest truth you find yourself telling high-achieving tech leaders who are used to having all the answers?

A: I used to think I had all the answers, too, until I was laid off in late 2023. It was the first time in my career that had happened, and it forced me to pause in a way I never had before. I had built my identity around steady progress and professional success, and suddenly that framework was gone.

That experience changed how I work with high-achieving leaders. I often share with my clients: you don’t have to rush into the next role just to prove you’re still “winning.” Giving yourself permission to slow down and figure out what you actually want is not a setback; it’s a gift.

Many people have spent decades running on pressure and momentum, moving from one demanding role to the next without ever stopping to ask whether it still fits. When that pace is interrupted by burnout or a layoff, it can feel terrifying. But it’s also an opportunity.

Yes, you can pursue another senior leadership role if that’s what you want. But you might also choose to start a company, consult, join a startup, buy a business, or pivot into something entirely new. I’ve done all of those things, and I help my clients explore those options with intention.

What we want in our 20s isn’t what we want in our 40s, 50s, or beyond. Priorities change. Energy changes. Definitions of success change.

I’ve experienced both burnout and job loss, and I’m grateful I took the time to reflect instead of reacting. Now I help my clients do the same, whether that means building an interim plan while launching a business, returning to W-2 work, or designing a completely new chapter. The goal isn’t just to land somewhere quickly. It’s to land somewhere that actually fits who they are now.

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Q: You went from building and hiring 1,000+ people to starting your own coaching practice at a stage when many might be thinking about slowing down. What advice would you give to someone over 50 who's considering entrepreneurship for the first time?

A: There’s a very different kind of fulfillment and pressure that comes with running your own business compared to being a W-2 tech leader. When you work for a company, you have a steady paycheck and benefits, but you’re also operating within someone else’s structure. And after everything I’ve seen, I no longer believe any company can truly guarantee long-term security.

What I value most now is owning my time. When I worked inside organizations, my schedule wasn’t really mine. As an entrepreneur, I have flexibility and autonomy, but that comes with responsibility. You’re accountable for everything.

Entrepreneurship can also be isolating, especially if you’re used to leading large teams. That’s why building a strong support system matters. I’ve been intentional about creating a network of mentors, advisors, and peers I can turn to for perspective. I invest in coaching, and I make time to meet people in person whenever I can. You don’t have to do this alone.

It’s also critical to build something you genuinely care about. When you’re aligned with the work, you stay motivated through uncertainty. The challenges don’t disappear, but they feel more manageable when you’re passionate about what you’re creating.

My advice is this: be thoughtful, build support around you, invest in your growth, and choose work that matters to you. Entrepreneurship over 50 isn’t about starting over; it’s about building something on your own terms.

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Q: Your LinkedIn profile mentions you're a "thrift-store treasure hunter" and "home-reno junkie" alongside your professional credentials. How do those personal pursuits inform your coaching philosophy about career reinvention?

A: I’m drawn to thrift-store shopping and home renovation because both tap into my creative side. I love finding something with history and potential and imagining what it could become. Whether it’s a vintage piece of clothing, an antique, or a forgotten piece of furniture, I enjoy giving it new life. People often ask me about what I’m wearing or displaying, and I love sharing the story behind it.

That same mindset shows up in our real estate projects. We’ve gutted and redesigned several properties, and right now we’re remodeling a 1979 A-frame cabin. Most people saw it as an eyesore. I saw a possibility. Having a vision for what something can become is what keeps me energized.

There’s something deeply satisfying about using your hands, your imagination, and your persistence to create something meaningful. And that’s exactly how I approach my coaching.

When I work with clients, I’m often helping them see strengths, ideas, and aspirations that have been there all along, waiting to be recognized. Like a good renovation or a great thrift find, career reinvention isn’t about starting from scratch. It’s about recognizing the value that already exists and reshaping it into something that fits the next chapter of your life.

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Q: You help clients negotiate $150K–$300K offers. What's the one negotiation mistake you see experienced professionals make most often—and why do you think it happens even at senior levels?

A: First, people don’t get clear on what actually matters to them before the offer arrives. I have every client start by writing out their non-negotiables and priorities for this next stage of their career - things like location, remote versus hybrid, benefits, vacation, compensation structure, growth opportunities, and the kind of work they want to be doing. Without that clarity, it’s easy to accept an offer that looks good on paper but doesn’t fit your life.

Second, many experienced professionals are simply afraid to negotiate. Even at senior levels, people worry that asking for more will cost them the opportunity. In reality, most companies expect some level of negotiation. When you accept everything as presented, you often leave meaningful value on the table.

I’ve helped clients secure higher base salaries, additional vacation, equity, bonuses, and more flexible arrangements. Very little in an offer is truly fixed.

Negotiation isn’t about being aggressive. It’s about advocating for yourself with clarity and professionalism. If you don’t ask, the answer is already no.

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Q: Between your time at L3Harris, founding DATalent, and now running your coaching practice, you've experienced corporate leadership, entrepreneurship, and solopreneurship. If you could go back and give your 40-year-old self one piece of career advice, what would it be?

A: I would tell my 40-year-old self this: don’t be afraid to take risks and don’t ignore who you really are.

Early in my career, I chose stability. I worked for the government because it felt safe and secure, and my parents were entrepreneurs. I thought that path would give me long-term security and strong benefits. What I didn’t realize at the time was that it also limited my growth. Over time, I began to feel stagnant.

I’ve always had a low tolerance for boredom. I’m not a “maintainer”. I’m someone who thrives on building, learning, and taking on new challenges. Once I accepted that, my career started to make more sense. Not everyone is wired that way, and that’s okay. But whatever your natural tendencies are, own them.

I also believe careers are becoming less linear. More people will design their lives around multiple income streams, flexible work, and evolving interests. My advice is not to let past choices, labels, or workplace culture define what’s possible for you.

Pursue opportunities that play to your strengths, stay curious, and give yourself permission to evolve. Your future doesn’t have to look like your past.

Finally, what is the best way for our audience to connect and engage with you?

You can find me on LinkedIn: https://www.linkedin.com/in/ruthsmithtechnology/

Or my website: ruthsmithcoaching.com

Seth Godin Quotes - I’m reminded of how good Seth Godin is with these quotes.

Dan Martell’s list of 20 AI tools that will actually allow you to earn. - These are legit.

Shared Spirits - Coming to your town soon. It’s like Venmo for Cocktails (Disclaimer: We have an interest in this company.)

The Ultimate Gig Economy Toolkit - It’s a free gift for newsletter subscribers.

A guide to starting a business after 50: From Kiplinger. A strong article.

Women finding success after 40, 50, 60, years old. You’re truly never too old.

Why companies are doubling down on virtual assistants: I told you why last week!

Dog walking wages: Turns out, you can make a living.

Our conversation with Nashville Artist Catron Wallace : Last week’s Over 50 Voice

The resume isn’t broken, hiring Is.

Dozens of articles on the topic of ageism, gig work, processes, and over 50 work.

The tools are getting smarter. That is obvious.

What matters more is what you choose to do with them.

For over 50 professionals, this is not about becoming a tech expert. It is about reclaiming leverage. It is about moving faster, testing ideas cheaper, and keeping more margin in your pocket while you build.

You do not have to master everything. You just have to stay curious and stay in motion.

This is not the end of expertise. It is the beginning of amplified experience.

And if you are willing to lean in, this might be the most opportunistic season of your career.

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Coming Next Week: Our Featured Article: How I’m using AI in my businesses.