Month: November 2025

Life has a way of stirring up an array of uncomfortable thoughts and questions, especially as we get older. Just when we thought we had things neatly organized and our past tucked away where it belongs, we’re hit with the dreaded, “What if?”

Women in particular often find themselves reflecting on the choices they made – or didn’t make – earlier in life.

Thoughts about careers, children, lifestyle choices, missed adventures, or dreams set aside for practical reasons can settle in like unwelcome guests.

What if,

• I’d gotten that degree?
• Pursued that career?
• I’d spent more time with family?

But as disconcerting as these thoughts and questions can be, they can also be great teachers and serve a larger purpose.

Mid-to-later life doesn’t need to be about staring backwards at all the closed doors. Instead, it can be the first time that the pathway to those doors is obvious, and the doors unlocked.

Sounds a little too Pollyanna?

Let’s explore.

Why Regrets and What-Ifs Are Loudest During Second Half of Life

Before we consider where we place and how we use those nagging thoughts, let’s talk about why they’re so loud right now.

In our 20s and 30s, life feels big and somewhat overwhelming. We’re dealing with the now and the urgent and believe there’s time to handle tomorrow’s problems tomorrow.

That’s not wrong, by the way. During those years it’s all about moving forward, getting established, and maintaining stability, sanity, and balance.

The choices you make, for better or worse, are the right ones for you and your family in those moments.

However, once we reach our 50s and 60s, our perception of time changes.

It’s like looking at the instant replay in a football game. From this vantage point, you can see things in a new light and think, “Oh, why didn’t I run that play differently?!”

This is when regrets can be triggered.

For women in particular, midlife years can amplify these feelings because of the truly pronounced transitions they experience.

• Children leave home.
• Marriage or relationships change.
• Menopause comes and goes.
• Retirement settles.
• Health concerns emerge.

And society doesn’t help, as it so often places a premium on youth vs. experience.

So, women can find themselves feeling displaced, lacking relevance, and with more time than is healthy to reflect on the roads not taken.

BUT – it doesn’t need to be like that. In fact, it absolutely should not be like that.

Reframing Regret as a Teacher

The first step in processing regret and “what ifs” is to shift your perspective.

Let’s look at some examples.

If You Regret Not Traveling More

It highlights the value you place on exploration and your curiosity about the world.

If You Regret Not Pursuing a Particular Career

Look at the aspects of that career choice that were most alluring to you. This shows the areas of work that are most meaningful to you and you can figure out ways to explore them now.

If You Regret Not Spending Enough Time with Family or Friends

The emotional elasticity of most people is pretty impressive, especially when it comes to family. So, this regret can serve as a direct call to action for prioritizing those relationships and reversing the impact of prior choices.

My point?

Once you see the value beneath the regret, you can actively find ways to honor that value now.

As a practical exercise for understanding these things more clearly, try the following:

• Write down the regret that’s weighing on you.
• Ask yourself, “What is this regret revealing about what’s important to me?”
• Brainstorm how you can focus on that value NOW, even if the original opportunity has passed.

Keep in mind that just because a specific opportunity or age of ability has passed, it doesn’t mean the value can’t be honored or that experience can’t be had. It just may be a bit different.

For instance, backpacking through Europe at 22 may now be touring Europe more comfortably at 60. Still fun and adventurous.

Turning “What Ifs” Into “What’s Next?”

Allowing yourself to embrace the excitement of “What’s next?” means first letting go of the emotional grip regrets can have on you.

So, to move forward effectively and with the least emotional weight possible, try employing these strategies.

Practice Self-Forgiveness and Compassion

As I mentioned earlier, when you were younger, you made the decisions you needed to make at that time. While hindsight may seem like 20/20, it’s not always fair.

Give yourself some grace and don’t let your current perspective color your past choices.

Share Your Story

Regrets thrive in silence. Telling your story to a friend, family member, or therapist can remove their power.

Create a Release Ritual

It may sound silly, but symbolically releasing your regrets can help you feel less burdened by them. It can also help you mark a turning point for moving forward.

Consider writing them down on slips of paper and then burning them or releasing them into water.

Focus on the “Yet”

Instead of saying, “I never tried that,” or “I never did that,” modify by adding “yet.”

“I haven’t done that – YET,” and “I haven’t tried that – YET” are much more powerful and optimistic.

Now that you’ve worked to let the “what ifs” go, your next step is to focus on what’s next by creating new experiences and planning for your future.

The following can help you get started.

Make a List of All the Things You’d Like to Try and Set a Calendar

If big things seem overwhelming, start small. Take a class, make some phone calls, do some research, or write a letter. Your approach will depend on your goal.

Set one goal for each month, and perhaps a larger goal (like travel) for each year.

Recruit Friends or Family to Join You (Or at Least Support You)

New adventures can be more exciting (and more likely to occur) when you have a partner and/or support from people you care about.

Surround Yourself with “Possibility” Thinkers

There’s a lot to be said for the influence the company you keep can have. Energy is contagious – both high and low energy.

Dealing with the regrets and “what ifs” that can occur during the second half of life isn’t about rewriting history. It’s about accepting the past, recognizing the value in the lessons, and determining the best way to move forward.

Regrets don’t have to cancel out potential, and they should be looked at as kindling for the fire that keeps your sense of self and excitement for the future alive.

Let’s Reflect:

Have you been dealing with life regrets? Have you found a way to process them and move forward? Please share your story and join the conversation.

There’s a lot more to it than you think.

They’re worthy of a mirrorball trophy.

Over the years, I’ve had my share of odd jobs.

As a teenager, I took them to make pocket money for the essentials – glossy magazines with pinups of the day’s hunks and disco dance lessons. I did everything from babysitting to working at a dry cleaner’s to typing invoices for a psychotherapist.

As I got older, I continued to seek out this kind of work when I needed extra cash, also for the essentials. You know, things like the gas bill, food, and rent.

And while I never delivered a singing telegram or developed strangers’ vacation photos in an hour (or less!), I’ve had some curious side hustles over the years. But the strangest had one thing in common: they were disguised as fairly mundane positions. Like the one I had as a call center operator.

A Second Job, Three Clients, and One Line I Wouldn’t Cross

It seemed completely unremarkable at first. I took it as a second job for spare change during the holidays. The hours were flexible, and the tasks seemed simple enough: read scripted greetings, key in orders, and sprinkle in the occasional, “Excellent choice!” or “You have great taste!”

I started with one client – a well-known purveyor of gadgets, memorabilia, and fun, nonsensical stuff. When customers called in, they were asked for item numbers only, not descriptions. Management said this practice helped avoid order mix-ups. It also provided opportunities to say (in my most professional voice) things like, “I see you’ve selected our fart clock. You have great taste!” or “You’ve chosen our ‘How to Seduce Women’ kit. Excellent choice!”

A couple of weeks later, a renowned lingerie manufacturer was added to my list. Taking orders for the items in their catalog provided a whole new set of surprises. It was educational, too. I discovered the demand for French maid outfits, from both men and women, was broader than I’d imagined and that some customers were very particular about their fabric preferences.

But when the call center added a lifestyle company geared to older adults to my roster, things stopped being funny. I was expected to incentivize callers – many of whom I imagined had limited incomes – to purchase add-on products. Operators were told we couldn’t deviate from the script. So, I quit that night.

Filling requests for flatulent timepieces and leather bustiers? I was happy to do it. Talking people into purchasing trees that “grow five kinds of fruit” or commemorative coins? Not okay.

Looking back, I realize how lucky I was to have the freedom to walk away as well as how much that job taught me. Every strange task, every awkward call, reminded me of the power of choice: what we’ll do for a paycheck, and what we won’t.

Why Some Say “Yes” to an Odd Job Today

These days, a number of us – even those who’ve retired or cut back on work hours – consider odd jobs to experience something different, have disposable income, or help pay bills. Personally, I’ve dabbled in areas I hadn’t considered before last year, from consultation opportunities to a short stint working for a matchmaker. Like many women in their 60s, I’ve learned that sometimes the most unexpected work brings the richest perspective.

Whether it’s out of necessity, curiosity, or simply a desire to stay engaged, many in our community find themselves drawn to the idea of taking a side gig. The reasons, as listed below, can vary. But we often learn the most about ourselves when we try something new, even if it’s a little outside of our comfort zone, which is something traditional retirement doesn’t always provide.

A Little Extra Income

With cost-of-living increases, a part-time job can soften the edges without a commitment to full-time hours.

Structure and Purpose

A few shifts or side projects can add a pleasant rhythm to the week and a reason to get out the door (or log on).

Social Connection

Light work brings moments of community you can’t always get at home.

Using What You Know

You’ve built decades of good judgment and skills that others will happily pay for.

Curiosity and Confidence

Trying something new can be invigorating. It’s also a low-risk way to test-drive a path before committing to it.

Not So Unusual After All

“Odd jobs” aren’t really that odd at all; they’re opportunities. They remind us that earning, contributing, and connecting don’t have an expiration date. Whether it’s for extra income, kinship, or the sheer joy of trying different things, these experiences can bring fresh perspective and unexpected confidence. Worst case scenario, you gain a story. (My call center job became storytelling gold!) Best case, you gain purpose, meet new people, and end up with a little cushion.

Every quirky gig, no matter how temporary or unconventional, can teach us valuable lessons about resilience and choice. We may not all find ourselves taking orders for X-ray specs or mystery tomato plants (and thank heaven for that!). But if we want it, there’s something powerful in saying yes to work that makes sense for us where we are right now.

You may also want to read Could a Side Hustle Gig Provide More Financial Peace of Mind in Your 60s?

Let’s Have a Conversation:

Have you taken an unconventional job or side hustle? Is it a decision you’ve been happy with, or do you regret it? Did you ever leave a position because you were uncomfortable with its requirements? Share your thoughts and experiences with our community.

In response to a recent article about reasons not to date common in women over 60, I received this comment:

“All valid points. What is holding me back is my weight (overweight now) and having been celibate for over 10 years, the thought of intimacy. My body has cellulite, rolls of fat, wrinkles, spots, etc.”

Unfortunately, this is one of the most common concerns among older women re-entering the dating scene – especially after a certain age.

If you are one of those women who looks in the mirror and criticizes what you see – your face, neck, arms, breasts, hips, thighs, tummy, tush, or veins, your wrinkles, your age spots, or your rolls (oh, the list goes on!) – you are not alone.

But you do have a poignant choice to make.

My Moment of Truth

I had my own moment of truth years ago, long before I was coaching women over 50 in dating and relationships. I was looking in the mirror, hating what I saw, and slowly abandoning my intimate life – not because I wasn’t interested, but because of body changes and not wanting to deal with the whole fact of having a body!

What I chose next changed everything. (I’ll tell you what that was in a moment.)

As a Dating Coach for Women Over 60

I’ve now coached thousands of women our age on dating, self-worth, and body confidence. Out of the 34 possible obstacles to finding and maintaining healthy love, this one – poor body satisfaction and low self-esteem around appearance – is on almost everyone’s list.

And here’s the inflection point you face. You have 3 choices:

Choice #1: Give Up

You can keep beating yourself up, blaming age, metabolism, social media, and Western culture for your insecurities. You can stay in the cycle of shame eating, overanalyzing your body size, and comparing yourself to younger women.

With this choice, you are likely to go in for quick fixes from the wellness industry or flirt with plastic surgery ideas, only to feel temporarily hopeful – and then you’ll be right back to “giving up.” You’ll feel powerless, and you’ll surround yourself with others who validate that powerlessness, but deep down you’ll know you are cheating yourself of some sorely needed self-love.

Choice #2: Accept Your Body Exactly as It Is

This one takes real courage. It means asserting that your physical appearance is not a problem to be solved.

The right person – the right match – will love you exactly as you are.

There are men who love rolls, don’t even notice cellulite, and think wrinkles are sexy.

Self-love and acceptance are magnetic. Your body language, your laughter, and how you carry yourself at a dinner date or when meeting new people on dating apps will reveal your self-love and make you attractive.

Reminder: Men aren’t nearly as critical as you are of yourself. (If you don’t believe me, read my post on what men actually want.)

Choice #3: Change What You Can, Accept What You Can’t

This one is the hardest – and the most balanced. It starts by acknowledging that, yes, your body changes over time. Fat distribution shifts. Hormonal changes and menopause alter your body in countless ways.

But you can influence your physical fitness, your well-being, and your attitude toward yourself. Small consistent actions – a daily walk, strength training, how you eat and drink – boost body confidence and vitality faster than any “quick fix.”

This was the choice I made. It started by changing my relationship to sugar, because it was doing the most damage to my body, moods, and self-esteem. As soon as I cut sugar, I felt better, rested better, slimmed down, and started to feel sexy again.

You, too, can feel sexually attractive, powerful, and desirable again.

The Truth About Attraction and Confidence

Here’s what I’ve learned in my years of experience coaching women daters:

The less you think of yourself, the lower caliber partner you attract.

Your perceived dating pool reflects your own level of self-love. It’s just another reason to really focus on how you treat yourself before turning your attention to the attention of others.

Finding and enjoying love after 60 isn’t about changing this or that about your body shape, per se; it’s about reclaiming true body satisfaction and feeling as alive and in your power as humanly possible.

Want to learn a better way of dating, one that helps save you from repeated disappointments? I made this free webinar for you.

You’ve lived through more than most people. You’re wiser, braver, and more capable of deep intimacy than ever before. So please – don’t let negative body image rob you of your next great love story.

Let’s Have a Conversation:

How has your body image reflected on your dating life? Has it stopped you from meeting new people? What would body confidence look like to you?