Front of the Check exists for one reason: to help experienced professionals claim ownership over their income and their future.

Welcome back. This newsletter exists to help you turn experience into systems, systems into income, and income into independence.

No permission required.

I’ve been a failed consultant numerous times through my career. In hindsight, I see why now. I simply didn’t add enough value.

I didn’t have systems, processes, and deliverables that moved the needle for prospective clients. I didn’t have a niche or targeted defined market in place. Most career transitions I’ve made in my life involved the desire to leave an industry.

I could do consulting work successfully today in areas around spirits and wine promotions, promo agency work associated retail and on-premise activation.

Ain’t gonna happen. Why not, you may ask?

Because there are bigger fish to fry. Helping you as an over50pro is now my calling. So know this. Each Front of the Check issue will bring my dead level best to offer some value to you as a reader.

Now, let’s move on!

Stan left his VP role with a plan. Deep expertise. Strong network. Twenty years of results. Six months in, he's billing $150/hour on Zoom 50 hours a week, wondering why independence feels like trading a W-2 for a 1099.

The uncomfortable truth: You're not consulting. You're job hunting on repeat.

80% of consulting businesses fail within two years. Over 50% of corporate refugees take two years just to match their old salary—if they get there at all.

The problem isn't your skills. It's the model.

Three Fatal Mistakes:

Trap 1: The Hourly Hamster Wheel - You bill time instead of value. Your income caps at available hours. You're competing with 28-year-olds on Upwork.

Trap 2: The One-Off Project Treadmill - Every engagement starts from zero. No recurring revenue. Constant sales pressure. Feast or famine—mostly famine.

Trap 3: The "Glorified Employee" Delusion - You work 40+ hours weekly for one client. All the stress of self-employment with none of the upside.

Consultants earning $500K+ stopped selling hours and started building systems.

MODEL 1: ACCESS RETAINER

Monthly fee for guaranteed availability and strategic guidance. Not hours—access.

MODEL 2: FIXED-FEE PROJECTS

Scope-based pricing tied to deliverables.

MODEL 3: VALUE-BASED PRICING

Fee tied to measurable outcomes.

Month 1: Audit your last 5 engagements for patterns. Identify 3 clients who'd benefit from ongoing access. Calculate your minimum viable monthly rate.

Month 2: Create 3-tier service packages. Draft retainer agreement. Build one case study showing business impact.

Month 3: Propose retainer to one existing client. Run one fixed-fee pilot with 20% buffer. Track hours vs. estimate. Adjust pricing.

Consultants earning $500K+ share these traits:

Your corporate expertise is valuable. But expertise without a business model is just expensive advice.

The question: Are you willing to stop selling hours and start building leverage? If you wish to discuss these topics. Schedule a chat. No cost. Your Over50Pro Sherman is ready to chat. Other resources available here as well. https://over50pros.com/

A CONVERSATION WITH EILEEN HARRIS

Eileen Harris is a seasoned executive administrative professional, promotions specialist, and wine educator who embodies the power of reinvention in the second half of life.

With more than two decades of experience supporting C-suite leaders, work she continues to do by the way, Eileen brings precision, strategic thinking, and relationship-building expertise to everything she does.

As the founder of Tastings & Co., she creates engaging, accessible wine tasting experiences for private clients, corporate groups, and community events—making wine education approachable, enjoyable, and confidence-building.

Her passion for learning is reflected in her formal training through the Wine & Spirit Education Trust (WSET), Certified Specialist of Wine (CSW) and continuing her education as a Texas Wine Ambassador and other advanced certification.

Blending corporate excellence with entrepreneurial creativity, Eileen represents a new model of the Over 50 professional: adaptable, growth-oriented, and committed to turning experience into opportunity. Through her work in promotions and wine education, she continues to prove that reinvention isn’t a risk—it’s a strategy.

Q: Your background bridges executive support, event promotion, and wine education — how have the skills you honed as an administrative assistant for a CEO translated into success with Tastings & Co. and your promotional work?

A: My background as a senior executive assistant gave me a foundation that translates seamlessly into my work with Tastings & Co. In supporting CEOs, I learned how to anticipate needs before they’re voiced, manage complex logistics under pressure, and represent a leader and brand with professionalism and discretion.

Those same skills are critical in wine promotion, where preparation, adaptability, and brand stewardship directly impact results.

I approach tastings the same way I approached executive support — with strong preparation, clear communication, and a focus on the larger business goal.

From creating an engaging tasting flow to adapting in real time to foot traffic and consumer behavior, I’m always thinking one step ahead.

Combined with my wine education, my executive experience allows me to turn technical information into approachable, compelling stories that connect with consumers and drive results.

Q: As someone who built a business later in life, what was the most surprising mindset shift you experienced when transitioning from corporate support roles to entrepreneurship in the wine and events space?

A: Building a business later in life was never part of my original plan. My path into wine started simply with enjoyment, then curiosity, and eventually education and hands-on experience working for others in the industry.

Along the way, I had so many people encourage me to turn that passion into something of my own that I finally took the leap.

Today, Tasting & Co is intentionally small — and I value that. I continue to work full-time supporting C-level executives, which allows me to grow the business thoughtfully, stay grounded, and remain deeply hands-on.

That balance keeps the work meaningful, personal, and aligned with why I started in the first place.

Q: Wine can be intimidating to many people — how do you make wine approachable and enjoyable for newcomers in your tastings and events?

A: Wine can absolutely feel intimidating, and I make it a priority to remove that pressure right away. I love engaging consumers who feel unsure or say, “I only like sweet wine.” I always reassure them that there’s nothing wrong with that — taste is personal, and their palate doesn’t need to “mature” to be valid.

I encourage people to drink what they enjoy and to order it confidently, especially in restaurants. In my experience, there are far more sweet-wine drinkers than the industry often acknowledges, and they deserve to be celebrated.

For newer wine drinkers, I focus on curiosity over rules. I introduce easy-to-find varietals and encourage exploration across styles — red, white, rosé, and bubbly — and from different regions.

By keeping the conversation relaxed, judgment-free, and fun, wine becomes something to enjoy rather than something to feel tested on.

Q: Promotion and marketing look very different now than even 5–10 years ago. What are some strategies that have worked especially well for you in building awareness for Tastings & Co. and connecting with your audience over 50?

A: Promotion and marketing have changed dramatically, but what’s worked best for me is staying genuine and relationship-driven. I’ve never aggressively pushed to sell Tastings & Co.

Instead, much of my growth has come through word of mouth and my work as a Brand Ambassador, particularly in the wine space.

That role allows me to engage people of all ages in a very natural, in-person way. Interestingly, many of the people I connect with over 50 are especially curious — they often ask how I got started and how I built this path later in life.

I’m always happy to share that story, because it resonates and potentially builds opportunities for them.

For this audience, authenticity matters more than trends. By focusing on real conversations, shared experiences, and approachability rather than hard selling, awareness grows organically — and those connections tend to be lasting.

Q:  Tell us about a moment — a challenge or a win — that fundamentally reshaped how you think about your work or your career after 50. What did it teach you?

A: My love of wine is what truly reshaped how I think about my career after 50 — and now, as I approach 60, that perspective feels even more meaningful.

It prompted me to step back and ask what I wanted the second half of my working life to look like.

What I’ve learned is that continuing to learn is essential as we age. Instead of chasing something entirely new, I chose to go deeper into something I genuinely love.

Studying wine, working in the industry, and eventually building Tastings & Co. showed me that growth doesn’t have an expiration date.

That realization changed everything. It taught me that reinvention doesn’t have to be drastic — it can be intentional, joyful, and deeply aligned with who you already are.

Q: Looking ahead, what’s one trend in the wine industry or in experiential events that excites you most, and how are you preparing to leverage that in your business?

A: One trend that excites me is the shift toward more intimate, experience-driven wine events.

People are less interested in being talked at and more interested in meaningful, hands-on experiences that feel personal, relaxed, and educational without being intimidating.

I’m preparing for that by keeping Tastings & Co. intentionally small and highly customizable.

I focus on creating tastings that meet people where they are — whether that’s first-time wine drinkers or curious explorers — and tailoring the experience to their comfort level and interests.

By combining education, storytelling, and genuine connection, I’m able to offer experiences that feel memorable rather than transactional.

That approach aligns perfectly with where the industry is headed and allows me to grow thoughtfully without losing what makes the experience special.

Q: Is there a question I missed? What would you like us to share that we may have overlooked?

A: One thing I’d love to share is my perspective on where wine is headed. With wine sales shrinking, I believe the industry has an opportunity — and a responsibility — to make wine more fun, more inclusive, and more approachable for everyone, from beginners to the curious to true enthusiasts.

That means meeting people where they are. Sweet wine drinkers deserve more representation on restaurant menus, and wine professionals — including sommeliers — should feel comfortable validating those preferences rather than correcting them.

No taste is right or wrong. Wine is personal, and it should be enjoyed with confidence and without judgment.

At the end of the day, if people are enjoying what’s in their glass, we’re doing something right.

As I end our time with Eileen today, I’ve reminded of something. Next time you run into your local wine or spirits shop or grocery store and experience someone behind a table offering you a sample of something interesting or delicious, be mindful of this.

All people have a story. Our lives and the lives of those with whom we interact are more complex and deep than we might imagine.

Cheers to you Eileen! You may find Eileen Harris at https://tastingsandco.com

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If you’ve already started to side hustle, Plan B, or new business of any kind, there is a chance you’ve not formalized important things like entity formation, banking, and record keeping.

Take a look at our “Turn Your Side Hustle Into a Real Business” course. It’s free to you as a reader of the newsletter. If you’ve gotten started on building your dream but haven’t yet taken steps to protect your interest, don’t wait.

Take us up on this free offering and we’ll be around to answer additional questions for you or refer you to some trusted pros. Click this link to take the course.

Coming Next Week: “How to recruit, hire, and train a virtual assistant.”