On a scale of 1-10, with 1 being lowest and 10 being highest, how would you rate your confidence? How would you define confidence?

I like this definition: confidence is the internal state of trust or reliance in something, whether it is your own abilities, the reliability of a person, or the truth of a statement.

At its core, it is the bridge between a thought and an action.

Confidence is most effective when it is grounded in reality. It generally exists on a spectrum:

“We’re going to win Sunday. I guarantee it.”

Joe Namath

64% of workers over 50 have seen or experienced age discrimination in the workplace. We receive 62% fewer callbacks even with identical qualifications. A 133% spike in ageism complaints occurred in a single quarter of 2025.

You've felt it in the interview that never called back. The meeting where your idea was ignored until someone younger said it. The job posting that called for a "digital native."

This isn't paranoia. It's a documented pattern and millions of people over 50 are living it right now. It isn’t tough to understand why older workers are taking hits to their confidence.

Successful workers over 50 combat this invisibility and grow their confidence through several data-backed strategies. Here are the top four.

1. Shifting from "Survival" to "Thriving" Mindset

Research suggests that a primary driver of confidence is a deliberate mindset shift. Instead of entering the workplace with the goal of just "making it through," successful older workers reframe their age as a source of power and wisdom.

The Data: A 2021 study from Georgetown University Medical Center found that key mental functions, such as the ability to focus on critical information, actually improve with age.

The Strategy: High-confidence workers use this data to validate their "wisdom capital." They document their problem-solving history (sometimes called a "wisdom journal") to provide internal proof of their value when external feedback is lacking.

Mindset is complicated. I work with a coach, Angus Nelson. In the first stage of our work together, we broke down self-sabotaging scripts. We dealt with baggage around money, self-worth, and past mistakes. He helped me develop mental frameworks that reinforce my every day confidence.

Everything starts with mindset.

2. Radical Visibility via Public Advocacy

Invisibility is often a result of slumping, both physically and professionally. Successful workers over 50 grow confidence by claiming space.

The Data: Research from The Interview Guys indicates that workers 65+ are the fastest-growing segment of the workforce (projected to grow 86% through 2024), yet 22% report having their accomplishments ignored.

The Strategy: To counter being ignored, successful professionals engage in Active Visibility. This includes:

Honing Public Speaking: Joining organizations like Toastmasters to ensure they are the ones presenting their ideas rather than letting them be absorbed by the team.

Strategic Networking: Shifting from applying for jobs (where 50% of older applicants report being asked for birth dates) to referral-based networking. Building cross-generational mentorships allows them to stay visible to decision-makers.   

I put together a free 7-day email challenge that walks through exactly how to do this with one action per day, every detail included.

For a free 7-day Network Re-Engagement Challenge - click here!

3. Competence as a Confidence Multiplier

Confidence is often a byproduct of self-efficacy (the belief in one's ability to perform specific tasks). Older workers who maintain high confidence levels are typically those who aggressively pursue new technical skills to dismantle the "digital immigrant" stereotype.

The Data: 33% of older workers report that colleagues assume they are less tech-savvy.

The Strategy: Successful workers use micro-learning (webinars, AI certifications, and online courses) to stay current. The act of mastering a new technology, such as AI or modern project management tools, provides a competence loop that naturally boosts self-esteem.

I was on a call recently with one of my Brand Ambassadors, a woman in her late 60s. She had to cut our call short to attend an online AI class she was taking. That type of behavior leads to increased confidence.

4. Leveraging Job Tenure and Stability

While younger workers (ages 25-34) have an average job tenure of 3.2 years, workers aged 65 and older average 10.3 years.

The Strategy: High-confidence workers lean into this "Stability ROI." They position themselves not just as employees, but as institutional anchors who provide the diplomacy, patience, and complex problem-resolution skills that younger cohorts often lack.

A confidence building exercise to try is assessing your many contributions to previous and current employers and then building an age proof resume. Try using the tool below to leverage your experience in new age proof confidence building ways.

CLICK HERE for The Over 50 Pros Age Proof Resume Guide

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A CONVERSATION WITH LOREN ARMENTI

Some people spend their careers learning to fit in. Loren Armenti spent hers learning to stop. A Blue Ocean Strategy Practitioner, Certified Exit Planning Advisor, and founder of Your Maverick Move, Loren has built a second-act career out of the very instincts that once got her in trouble in Catholic school: curiosity, rule-breaking, and an allergy to conventional thinking.

Based in greater Philadelphia with over three decades of experience spanning finance, executive coaching, and CEO peer group facilitation, she now works with business owners and C-suite leaders to help them stop competing and start dominating by going where their competition simply isn't.

But what makes Loren more than just a strategist is what she does with the wisdom she's accumulated: she mentors Villanova business students, coaches veterans transitioning to civilian careers through FourBlock, and fosters pets of deployed military members through PACT for Animals.

At a stage in life when many are thinking about slowing down, Loren Armenti is doing what she's always done, asking why things are the way they are, and quietly rewriting the rules.

Q: You've built a career around helping business owners stop competing and start dominating their own market space. What was the "maverick moment" in your own life that made you realize conventional thinking was holding you back?

A: Such an interesting question!  For better or worse, I finally came to the realization that "conventional thinking" was holding me back about 10 years ago.

I went to Catholic grade school & undergrad.  And, as all loving parents do, mine wanted to set me up for the best chance of success.  In their minds that seemed to mean "fitting in".  In hind sight it seemed as though the well-intentioned grown ups in my life guided me to "unlearn" just about anything that made me uniquely "me".  Turns out, I'm a bit of a curious, day-dreaming, rule-breaker - - not exactly welcomed in Catholic School or a conservative home.  Ironically, these very traits have been my greatest guide in this chapter of my career.

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Q: Blue Ocean Strategy is built on the idea of making your competition irrelevant rather than trying to beat them. For a business owner over 50 who has spent decades in a crowded industry, what's the first mental shift they need to make to even begin thinking that way?

A: There are countless ways to begin. 

Resist the habit of continuing to focus on the competition and redirect your focus to your INDUSTRY.  By continuing to give attention to competitors, you stay stuck imitating the competition instead of solving ignored problems, creating a new offering and attracting new customers - - resulting in owning that space void of competitors.

Start by asking  yourself, "what's the most annoying thing our industry expects customers to tolerate?".

You already know where the competition IS.  The "chess move" is to identify where the competition ISN'T relative to the offerings in your industry.  Identify those unaddressed pain points currently overlooked (trust me - - there are MANY regardless of the industry).  
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Q: You hold both a Blue Ocean Strategy Practitioner certification through Blue Ocean Strategy and the CEPA (Certified Exit Planning Advisor) through Exit Planning Institute as a designation. Research shows that about 75% of business owners profoundly regret how they exited their company. Why do you think so many owners wait too long to start thinking about what's next?

A: Transitioning a business is not unlike any long-term relationship.  Similar to a marriage, it's hard or maybe nearly impossible for most founders who've often spent decades building their business to imagine an identity beyond the business.

Founders often fail to or procrastinate diving deeply to answer the often intimidating and overwhelming questions, "Who am I without my business?" and "What am I going to DO next?".

This transition often catches founders by surprise as being unexpectedly emotional.  When owners finally begin processing this realization, many describe it as "terrifying".  It's real, unfamiliar and often overwhelming.

Entrepreneurs are often used to being THE person people in their organization go to for answers.  If they happen to be over 50 years of age, these owners grew up in generations that were often left to their own devices as kids & simply didn't ask for help.  They're used to figuring stuff out on their own. But this?  This is different.

For starters, it's emotional.  Often not familiar territory for the over 50 crowd & often less so for entrepreneurs.

Without intentional and guided preparation, they quickly learn that golfing or fishing every day for the next 25 years isn't a solid plan for their next chapter.  Transitioning their business doesn't mean their life is over.  It means that they have the opportunity to intentionally design their next chapter during which they do things they enjoy & often offload the rest.  It might even mean being involved with another business.

There are many things required for an entrepreneur to have a successful next chapter post business transition.  Three basic pillars to build on for a happy, healthy and successful next chapter are to identify at least one thing to stimulate them in each of the following ways, which is a formula for any stage in life:

Intellectually

Philanthropically

Socially
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Q: You describe yourself as someone who has always viewed rules as "mere suggestions for consideration." How has that mindset served you differently in the second half of your career versus your earlier years?

A: My first couple "big girl" careers were in heavily regulated industries: first HR and then finance. In hindsight, I can now see that one of the things that set me apart in both of those arenas was researching & implementing creative and sometimes unconventional solutions to satisfy unique needs and client requests.  When I was in my early 20's I thought nothing of calling up the Insurance Commissioner in any state & asking if an exception could be made for a rule, clause, exemption, etc. - - and often being accommodated.  Obviously, this is going back to a different time. But, in my younger mind I thought, "What not?.  If you don't ask, the answer will always be, 'No' ".

Facilitating CEO peer groups and becoming a certified professional coach was a pivotal segway between a career path with expectations of conformity and one encouraging creativity.  This is when I was truly encouraged to develop my sense of curiosity and explore different perspectives.  I remember my father telling me that I would never be successful facilitating CEO peer/mastermind groups because I couldn't read a balance sheet or financial statement, which was true.  Challenge accepted.  This is when I began to learn that success of a business is determined by many more factors NOT found on a balance sheet.  Turns out that about 80% of the value of a business is NOT found on the balance sheet.  Take THAT, Daddy-o . . .

At this point in my life, there's something liberating about being over 50 and out of . . . patience.  I've adopted the understanding that we're all sovereign beings.  As such I believe we need to be our own best advocates.  Whether in business or personal scenarios, I'm more confident in evaluating situations and circumstances through the lens of curiosity and asking questions like, "Why is this the way it is?  Why is it done this way and what's the history that got us here?  Is there a better approach over all or for these specific set of circumstances? Is there a conflict of interest?  Who does the conventional approach best serve?".  Essentially, getting back to my roots as a curious child.  It's served me well.
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Q: You work with CEOs and C-suite leaders as a coach, and you also volunteer mentoring Villanova students and supporting veterans through organizations like FourBlock and PACT/Operation Foster. What does giving back mean to you at this stage of your life and career?

A: I believe in paying things forward and helping where we can. 

If I can provide guidance to a young student embarking on their career path by giving them perspective and confidence, that's a win.  Mentoring young business school students gives me a chance to share insight I would have benefitted from hearing as a younger version of myself.

Being a bit of a rule-breaker I don't think I'd fair very well in the military.  I barely made it through Catholic school.  Plus, I certainly don't have the courage to go through what our Veterans experience.  Yet, I'm deeply grateful for their dedication and sacrifice for our freedom.

Helping Veterans transition from their military to a civilian career or giving a Veteran a little peace of mind knowing their beloved pet is well taken care of until they return instead of often having no other option than to often surrender their beloved pet to a shelter upon deployment (often resulting in euthanasia due to overcrowding) seems like the least I can do. 

Shameless plug, both FourBlock and Operation Foster/PACT are always looking for volunteers!
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Q: A lot of business owners over 50 are simultaneously thinking about scaling their company AND thinking about what an eventual exit looks like. How do you help someone hold both of those goals at once without losing focus?

A: Business growth and transition need not be an "either-or" decision.  Building enterprise value gives owners more strategic flexibility and control to decide whether to continue growing, step back OR transition the business.

There's no rule stating that the owner's business needs to be sold all at once.  If the owner has time on their side, repeating the strategic cycle of selling part of the business while continue to grow the retained portion might be a preferred strategy.

Additionally, according to research conducted by the Exit Planning Institute [I haven't located the source], business transitions are involuntary about 50% of the time due to either death, disability, disagreements, divorce and/or distress (A.K.A.,"the 5 Ds").  

Also consider the reality that for most business owners, their business comprises approximately 80% of their net worth.  To put that into perspective, 80% of the typical business owner's net worth is comprised of one single ILLIQUID asset. 80%!!

If the owner(s) has not intentionally engaged in the strategic exercise of building enterprise value, LOTS of dollars are needlessly unrealized.

"Exit Planning is good business strategy." ~ Christopher Snyder, author of  "Walking to Destiny"

"The best company to run is one that's ready to sell." ~ Christopher Snyder, author of  "Walking to Destiny"
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Q: If you could give a 60-year-old one piece of advice about starting a business that allows for freedom from stress, what would it be?

A: Begin with the end in mind.

One of the top 3 drivers of business value is the ability for the business to run independently of the owner.  Build & surround yourself with a top-tier team.

And, what about that 80% of business value that's NOT found on the balance sheet referenced earlier?  It's found in the intellectual capital (structural, human, social and customer capitals).
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Q: How can our audience best connect with you? 

A: Thank you for asking.

Email: [email protected]
Ph: (610) 716-5558
Web: YourMaverickMove.com
LinkedIn: https://www.linkedin.com/in/Loren-Armenti-Your-Maverick-Move/

Joe Namath Quotes - The epitome of confidence.

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Today’s best gig economy platforms: If you want free training on some of these, visit Over50pros.com

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

You’re doing $15 Tasks with $150 Talent: We have a VA at the ready for you! Reach out to me for details. https://calendly.com/over50pros/new-meeting

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I love today’s featured topic. Confidence. It’s something we’re born with. How is that, you may ask? In the absence of criticism, we act boldly.

There isn’t a single universally agreed “average,” but a widely cited figure comes from early childhood behavior research and parenting literature:

By around age 5–6, a child may hear “no,” “don’t,” or similar negative/scolding language roughly 20,000–40,000 times.

How does one even begin to grow in confidence with this barrage of negative feedback? Is it any wonder that we have to mentally rewire years of programming to feel confident?

Confidence is a muscle. Start with something minor, not overly stress inducing. Practice doing something uncomfortable. Popular author and entrepreneur Tim Ferris suggests simply laying on the floor in a busy place just to endure what people will think.

Let’s grow our confidence together. I’ll be more bold if you will! Or perhaps, I’ll lead the way.

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Coming Next Week: Our Featured Topic: Platforms that deliver opportunities. Pros, cons, and how to leverage them.