• My 21-year-old son wanted to visit a lively beach club during our family vacation.
• I never expected my parents, both in their 70s, to get up and dance to ABBA.
• Seeing their joy reminded me that getting older doesn't mean giving up new experiences.

My 75-year-old dad told me he'll feel like he's closer to dying if our annual family vacations stop. He's not ready for that. Neither am I.

It stopped me in my tracks and frankly scared me a little. While I know my parents are aging, I haven't begun thinking about life without them, and I found myself spending the rest of the vacation looking through this new lens.

For the last 12 years, my husband, my parents, my son, and I have traveled all over the world on an annual multigenerational trip. And while the sights have been spectacular, what struck me most on this last vacation is just how much each of us has grown to value these trips.

I'm in the middle between my parents and my son

The dynamic has certainly evolved. My son was 9 when we started, is now 21, and brings his girlfriend along. My parents are now in their mid-70s, with some health challenges that require more patience and care. And I'm in the middle, adjusting the trip so everyone can still participate. I used to plan for adventure. Now I'm thinking about walking distances, downtime, unpacking, and what my parents can comfortably do, while still making it fun for the 21-year-olds.

But what I learned on this trip was that sometimes, when choosing something for the youngest generation, a magical memory is created for the oldest, like when we went to Nikki Beach in St. Tropez at my son's request. We had been there for lunch a few years prior, and we wanted to return, this time when we could see the true Euro summer beach club vibe in action, complete with waving white napkins and ABBA blasting from the DJ booth.

I never would have guessed it, but both of my parents were up and dancing that day. My mom has since declared the whole day one of her favorites. Who knew? Maybe all they need is a "darty" (day party, as my college kid tells me!).

These are not just vacations for my parents

After what my dad had said earlier in the trip, I watched him differently that day. Seeing him dancing with my mom, laughing and completely in the moment, I understood a little more of what he meant. These trips aren't just vacations to him. They are something he still gets to look forward to, proof that there are more places to go, more memories to make, and more life ahead of him.

The thing is, for the first few years of these trips, I just wanted to knock places off my bucket list. Now, I want to figure out how to bottle the time and have lasting pictures in my head because a time will come when they stop, when it is no longer feasible for my parents to travel, and when my son will be busy with work and his own family.

I know the finality of life all too well, as I still struggle with the loss of my son Jake after 15 years. I know firsthand the fragility of life and how it can all change in an instant.

My dad's comment also made me realize that I've been thinking about these trips mostly from my own perspective as planner and caregiver. I worry about how much walking they can do, whether they need an afternoon off, or if I've planned too much. He's thinking about something entirely different. He's thinking about what it means to still be able to go.

The goal is to spend time together

The success of these trips used to be measured by where we went and what we saw. Now they are measured by how much uninterrupted time we have together. As we've shifted from bucket-list places like Africa and the Galápagos, we've begun to choose places where we don't have to pack and unpack every three or four days, where we can settle in and spend time together.

We've all learned that the real moments of these trips do not lie in the over-the-top experiences. They lie in the moments after the excursion, when we are all having cocktails by the pool and sharing time, the most valuable gift we all have. It's in the final glass of wine, listening to music, or playing Flip 7 or Pass the Pigs. It's when we are tired from exploring and stop to have a beer on a random street in a random place that we may never find again.

I don't know how many more years the five, now six, of us will be able to do this together. I hope it's many. But my dad's comment made me realize that counting the years almost misses the point. We got this trip, and while we were there, everyone could still dance.

Perhaps the most important thing is that when my parents started this tradition all those years ago, they started something that won't end with them. I know someday these trips will be for my son and his family. I love knowing my parents gave us that tradition. I'm just in absolutely no hurry to inherit it.

• My husband is 23 years older than I am, but our age difference never bothered me before.
• Now that he's 61 and we're raising two young kids, I'm noticing our different energy levels.
• I love our life together, but I'm struggling with the realities of our age gap.

When my husband and I first met back in 2014, we had what many would consider a whirlwind romance. We met, fell in love almost instantly, moved in together after a year, got engaged six months later, married a month after that, and a little over a year later, welcomed our first child.

It was all very exciting, rushed, and filled with emotion and love.

I'm also a very rational person who doesn't get easily swept up in the moment. So we talked about a lot of the "hard" decisions that couples so often neglect to discuss at the beginning of a relationship. We talked about children, our future, and what we wanted our lives to look like. That's why, now, more than 12 years later, it's surprising to find myself struggling with something I thought I had already made peace with: our age gap.

He is 23 years older than me

My husband and I have a 23-year age difference. Yes, I was always aware of it. And, to be honest, it never really made a difference to me.

Especially when it came to the big life decisions, including having children, we had those conversations before we even got engaged. I knew exactly how old he was. I knew there would be things about growing older together that would be different for us.

But I guess there's a big difference between being aware of something that could eventually happen and actually living it.

Our age difference has been showing up in more ways than one lately, and there's a part of me that's angry with myself for being surprised by it.

It's not like my husband was always going to be the 48-year-old I met when I was 25. I knew he would age. I knew things would change as he got older. I knew there would eventually be a point when the difference between us became more noticeable.

I just don't think I ever wanted to admit to myself exactly how much.

He's in his 60s now

I knew he was going to be an older father. I knew all of this. But knowing something and seeing it firsthand are two very different things. Lately, I've seen just how much his 61 years are catching up to him, and it's been putting me in a strange place.

I keep a lot of things together for my family. We have two young children, and I have my own business. There is already a lot that weighs on me. But what I've noticed recently is my husband's physical health beginning to catch up with his age.

Don't get me wrong — my husband is in great shape for a 61-year-old. But at the same time, most 61-year-olds aren't running after toddlers or handling the daily insanity of school drop-off and pick-up.

And that difference is becoming harder for me to ignore. What bothers me most is how naive I feel. I knew this was a possibility. Quite frankly, my husband knew it, too. When we discussed having children, we were always on the same page, but he expressed his concerns about being an "old" dad. I heard him. We talked about it. We made the decision together.

And yet, now that I'm watching the reality unfold in front of me, I'm beginning to feel guilty. As though I've been selfish. As though somehow this isn't fair to my kids.

I see how much fatherhood — and, frankly, being a husband — can weigh on him.

The everyday insanity of being part of a household with a high-maintenance 8-year-old and a very independent 3-year-old is a lot for anyone, myself included. But it's especially a lot for a 61-year-old.

Sometimes he physically can't keep up with our 3-year-old, who runs at a pace that could outrun the best of us. Sometimes he mentally can't keep up with our eight-year-old, who talks at about a million miles a minute.

And those moments make the age difference feel very real.

It's not just the fatherhood aspect

I feel his patience with me beginning to waver, too, and I wonder how much of that is because we're simply in such different phases of life.

I have a thriving public relations firm, and I feel like I'm just getting started. I have energy and ambition and a feeling that there is still so much ahead of me.

He had a contracting firm for many years, but that chapter of his life is well behind him now. At his age, he should be enjoying retirement. Instead, he's a stay-at-home dad and handles a huge amount for our family. But he's far from retired.

He's the only one who drives, so he's the family's chauffeur. He makes appointments and handles logistical things. He oversees the renovations on our house. He does the grocery shopping. He does so, so much.

And the truth is, at this age, maybe he shouldn't have to.

Our relationship itself hasn't really changed. We are still very lucky to have an incredibly open and loving relationship. We talk about these things. We try to give each other space and understand where one another is coming from. We each do what we can mentally and physically for each other, for our children, and, just as importantly, for ourselves.

I think what we're realizing is that neither of us has ever been here before.

We knew there was an age gap when we met. We knew what it meant on paper. We talked about the difficult possibilities before we got married and before we had children.

At 25, I could understand that my husband was 23 years older than me. At 38, I can feel it.

• Years ago, I made fun of sports parents who went all out and spent thousands on their kids.
• Now I'm one of them.
• Last season cost our family over $8,800. Looking back, I have no regrets and would do it all again.

Ten years ago, I was the mom making fun of select sports parents. I thought they were crazy. Nuts. Over-spenders. People who didn't understand priorities, or budgeting, for that matter. Then I became one of them.

It didn't happen overnight, but gradually. My then-7-year-old son was asked to try out for a team. At the time, it seemed more competitive than the rec league he had been playing in, but not overly so. Practice times doubled. Costs also doubled. The following year, it happened again, and they doubled again. And now, I'm a mom of 5, with an 11-year-old who is obsessed with his select baseball team. Well, career. It's called a career, he's told me.

And that would be fine, but it's the unexpected costs that really caught me off guard. Over time, I got used to the idea that team fees would pass the three-figure mark. I was okay with that, because I saw the joy it brought him and realized that he's a young athlete who is more naturally competitive than rec teams typically allow for.

What I didn't anticipate were the extra costs. Here's how much it really costs to be a select sports family. And as select sports families might note, this isn't even for the most competitive, select travel teams in our area.

The real cost of select sports for our family

Growing up as a competitive gymnast, I look back and realize what it really meant for my single mom to shell out $90 for a competition leotard — and that was 25 years ago. Now, I see just how those extras add up and can tank a budget unexpectedly, one little overpriced concession stand hot dog at a time.

If I sit and add up the cost of the sport, which I do periodically, I find that it's a lot, even if I'm focusing on the more conservative end of our expenses. Here's how last season played out for us:

• Concession stand spending: $40 per game, estimated at $2,000 for last season. Our family of seven attends 40 to 60 games a season. Yes, we could pack our own food, but here we are, imperfect and flawed parents, just trying to find a uniform 10 minutes before warm-up.
• Gas: at least $700 per season. Our local practice field is over 20 minutes away so we do our fair share of driving for the sport. We also have tournaments in cities that are hours away, our furthest was about a 5-hour drive. In a season, this accounts for 10 to 12 tanks of gas, which of course varies with the price we pay at the pump. If we drive our large Sprinter van with the whole family tagging along, it's even more.

• Gear: around $1,250 last season. I consider myself a slightly scrappy shopper, having grown up on garage sale gear. So as an adult, I try to walk the line of buying new items, such as baseball gloves and pants (used pants at this age are often very worn), cold gear for chilly practices, hats, gloves, catcher gear (used on eBay), cleats, socks, and more. Then, there's gear from the actual team, such as belts and casual wear like hoodies and shorts. None of this includes the overpriced composite bats, which range from $200 to $500 apiece and come with the promise of "hitting bombs." Sure, we don't buy everything new every season, but looking back over my credit card bills reveals this past season was a pricey one.
• Private lessons: $300 a month for six months. As anyone with a semi-serious athlete knows, regular practice never seems to be enough. When my son became a catcher, we had to, well, catch up and learn catching. When he hit a mental block with hitting, his private lesson teacher scheduled extra sessions.
• Babysitting: $600 last season. When a game starts at 8 p.m. and ends after 10, parents with little kids need other options. Sometimes, we have our local babysitter chip in and help the other kids maintain a more normal schedule, including bedtimes. This can add up, but sometimes it's just nice to watch your older kid play without toddlers climbing on you with sticky hands. We pay our sitter $25 an hour and used them several times last season.

• Parent gear: $400 last season. Parents are the fan club, and they need to look the part. Even if each parent buys just an item or two from the team pro shop, it adds up. I might have also grabbed the super-cute Bauble Bar Perfect Catch Earring Set this year, along with team-colored HOKA sneakers for lugging gear around the city and getting some steps in during warmups. Finally, with so many kids, we invested in a double-decker wagon that hauls kids, chairs, drinks, snacks, and diaper bags from game to game.
• Hotel stays: $1,200 for four nights away. I know this is lower than many teams with a heavier travel schedule, but our cost is higher because we need a suite or two rooms for our large family. Teams often require these stays, and hanging out in the hotel pool is a big part of the kids' memory-making that can't be skipped.
• Registration fees: $900 per season. There are options to fundraise for parts of this, but I very rarely feel good about asking others to pay for my son's sports. I know it works for some people, but for me, going to the same people over and over to chip in feels off (aside from the grandparents who are always down to buy a coupon book).

The total isn't the point

When I say I really don't want to add this list up, I mean it. But for the sake of other parents who feel stressed about so much of their family budget going to sports, or those who need a real look at what it entails, I will.

Before I do, though, I have to acknowledge what all these extras mean for my son. The movement outside instead of getting addicted to screens: priceless. The self-esteem and confidence gained by overcoming stress in a high-pressure game: priceless. The camaraderie and friendships on a team: priceless. The bonding experience of watching the sunset with toddlers screaming their brother's name and number: priceless.

The grand total for the past season landed around $8,850, give or take a bag of popcorn or four. I'm off now to get a second job.

Spring signups are happening soon. I'll do what I can to save, and hope my son doesn't need a new bat, but I know I'll gladly be paying close to this again for yet another season. After all, the popcorn is decent, and my son's joy is contagious.

• My husband and I lived in NYC for six years before becoming parents.
• We have plenty of memories there, and recently went on a family trip with our two girls.
• We didn't get to do a lot of things on my itinerary, but I'm still grateful for our time.

New York City was home to my husband and me for six years before we had kids and moved to Asheville, and it will forever be a place that holds so much for us. That's why when the timing, cost, and opportunity aligned for our family of four to vacation there for a week recently, I was chomping at the bit to return, enthusiastic at the prospect of sharing this colossal, important place with our 4- and 6-year-old daughters.

It was easy to have high expectations for a trip down memory lane, but the reality is that any trip with kids will be what it will be, and we can only hope that something along the way — a bump in the road, a detour, a singalong — cements into their memories and crystallizes into sentimental gemstones that they turn over and over in their minds with time.

I created a full itinerary for our trip

Leading up to departure, I planned a weeklong itinerary with suggestions for each day on where to go, what to eat, who to see, and what to do. Knowing my kids would need some rest and recovery, I built in plenty of downtime — or so I thought. Still, as with all things parenting, I was rudely reminded that even with my experience and expertise as Mom, I could not foresee every breakdown.

By midweek, my daughters hit a physical, mental, and emotional wall. I had planned to take them to the Met, but instead, I was met with loud, convincing pleas to spend a couple of hours in the hotel room. Crestfallen, I agreed. They didn't know about the daydreams I'd had of walking them through the museum to see the Temple of Dendur, the Medieval Sculpture Hall, and rooms where Degas's ballerinas, Monet's water lilies, or Van Gogh's self-portrait lived. Sigh. I'm an art lover — I enjoy meandering through vast halls and admiring human creativity and intellect. It brings me great peace and joy.

I was disappointed that we didn't go to any museums

A few days later, I found myself in the same situation at the Whitney. My generally agreeable kids protested once again, so we switched gears. We took a stroll on the High Line, grabbed pizza from Chelsea Market, and landed at the Diller — von Furstenberg Sundeck & Water Feature between 14th and 15th Streets. There, they were all smiles — delighting in the sun, in the relief of cool water, barefoot, holding up their dresses, splashing, squealing, happy.

My kids are still young — 4 and 6 — and have only experienced small art museums. They don't even know what they're missing! So, naturally, when it was clear that we weren't going to visit any art museums, reality stung. This is one of the painful aspects of parenting: accepting that the things you really want to do just don't happen for one reason or another. Of course, you could force your child to do what you'd like to, but what memory does that create? What good does that serve?

However, I realized that there would be other trips and was grateful for the time we had

I let out another deep sigh and told myself, It's OK. There's always next time — hopefully. I smiled, thinking about the next time, and I began to daydream once again. All was well. What mattered most to me on this trip was visiting the place we once called home and introducing it to our girls — acquainting them with the place their mother and father made countless memories, befriended incredible people, grew stronger in their marriage, became parents during a pandemic, and tearfully bid adieu.

Parenting continues to be one wide and winding journey, where I'm constantly toeing the line between curating memories and allowing memories to make themselves in the most ordinary of places: on the 32nd floor of a hotel room, on a playground in Central Park, on a Subway train, on a city bus, on an airplane in the clouds.

In addition, I'm still learning that parenting is mostly a selfless act. Yes, there are moments we get to share with our kids that allow them to see what fills us up as human beings, but it's often an unwieldy and imperfect balance.

Many of the decisions we make come at a cost, and, for this trip (and future trips), I'd rather the cost be one that I pay — not them. Their joy is my joy. And, in this chapter of life, it's bigger, grander, more powerful than any selfish indulgence that life has ever afforded me, and, honestly, I'm here for it. I'm grateful.

• I'm an Airbnb Superhost with an average rating of 4.9 stars from 90 guests.
• Everyone is buzzing about the new rules that limit the chores hosts can ask guests to complete.
• I support the change. Guests are paying to use a space, their last memory shouldn't be a checklist.

The internet has been buzzing about Airbnb's latest policy change over restrictions on what a host can — and cannot — ask a guest to do before they check out.

I've been renting my home in the Hudson Valley for five years, and have been a Superhost since 2023. Currently, I have 90 guest reviews with an average rating of 4.97. That's not an accident. It's something I work hard at.

Though the property management company I work with hasn't always loved it, I've never been big on requiring guests to follow a strict cleanup policy. While we did ask for dishes to be done at one time, that hasn't been part of my guest instructions since 2025. For me, the most important tasks are to turn off the lights and return the key to the lockbox before guests leave. Beyond that, I don't expect much else, though I know that hasn't been the norm for some Airbnb users.

Guests are still guests

Somehow, the B&B part of the nomenclature appears to have gotten lost. I've seen users who fear bad reviews if a place isn't meticulously cleaned, voicing their concerns on Reddit and Facebook. For me, that's not something I think someone should have to worry about when they're paying to use a space.

While there are legitimate stories of guests destroying a place or leaving it in shambles, this hasn't been my experience. I believe the majority are good guests.

There is still a cleanliness rating for hosts to fill out about guests, so I imagine that even without imposed rules, most will do the dishes anyway. Leaving a bag of trash inside the house shouldn't result in a host docking a star or two from their review. It should be part of the stay, especially since hosts can set a cleaning fee for their property upfront.

I am glad the company has intervened on behalf of the guests. They are staying at a vacation rental, not a work exchange.

Hosts like me can have little time between bookings

I understand the rationale behind hosts who have lots of rules. There is often a small window between turnovers, and hosts want to make sure they have enough time to wash and dry everything before the next guests arrive.

It's something I worry about, too. That's why I keep extra linens and dishes on hand. They're there to use just in case there isn't enough time to complete everything between the bookings.

At one point, my property manager and I disagreed over what we wanted guests to do. I felt as if he was taking it personally if someone left dirty dishes in the sink or didn't sweep up. With this rule change, we'll no longer be at odds, and I'm glad.

Most guests have been respectful of the space

I am fortunate. I have rarely had a guest be anything less than tidy, and I have also had hardworking cleaners who have taken linens home to wash because turnovers have been so tight.

None of my guests have complained about my rules directly to me or in the comments they've left online about my property. I intend to keep it that way.

I host because I enjoy it

Everyone has their own reasons for getting into this business. For some, it is purely fiscal, but for me, it has been personal. This is my house, and I take tremendous pride in it and the surrounding area. I vet each potential guest personally and hand-pick a welcome gift for them. I want them to have a lovely stay, leave with fond memories, and maybe even a desire to return one day.

The last thing I want a guest to do is worry about a lengthy checklist of tasks before leaving. I don't want that to be their last memory of their stay.

Soon, a mother and daughter will be staying at my property for the third year in a row. In my emails to them, I wished them a safe journey and said we would take care of the rest — and I meant it.

• Jen Eaves' mother is 79 and lost more than $3,000 to online scams.
• Eaves now monitors her mother's finances and says that was a hard conversation.
• Digital caregiving is an important part of supporting aging parents, she says.

This as-told-to essay is based on a conversation with Jen Eaves, Digital Caregiving & Elder Fraud Advocate at Aura. It has been edited for length and clarity.

It's an odd shift in dynamic when you start caring for the people who always cared for you. My mother is 79, and lives with my brother, who handles most of her day-to-day physical care. I'm the one who handles the administrative side of care, like scheduling doctor appointments and keeping her safe online.

About six years ago, my mom had a stroke, and while she recovered fairly well, she wasn't the same cognitively as she had been before. Around that time, I began noticing her falling for scams online.

Once, she ordered a cure for diabetes, which she has. The product was supposedly being sold by a famous TV doctor. When she showed me the video ad, I could see it was badly done AI, with the supposed doctor's lips not matching his words.

There have been other scams and pitfalls, too: online orders that never arrive, or even a legitimate credit card that my mom opened without realizing what she was doing. All in all, she's lost about $3,000 to scams, though I've been able to recover most of it through her bank.

I've realized that I need to take a more proactive approach to digital caregiving to protect my mom's finances. Here's what I'm doing.

Approaching from a place of help and dignity

After my brother and I had taken my mom's keys away, her phone became her connection to the world. I wanted to respect that. While some people have to restrict their older parents' access to phones, that didn't feel right in my case.

It was critical to me that my mom kept her dignity and as much independence as possible. At the same time, I saw there was an emotional side to falling for a scam: she would feel frustrated and confused when it happened, and I wanted to spare her those negative emotions.

I never want my mom to feel like I'm parenting her. Instead, I pointed out the patterns I was seeing and emphasized I'm here to help if she's willing to let me be involved. The choice, ultimately, is hers. This would be a lot harder if she wasn't willing.

Talk about scams

My mom wasn't particularly tech savvy, even before her stroke. I've had to educate her about what scams look like. When she shared the famous doctor video, I pointed out the aspects that seemed AI-generated to me. I remind her that if it sounds too good to be true, it probably is. I emphasize that urgency is a big sign of a scam. The bank, I tell her, is never going to call you.

Once, she had a scam caller claiming to be Apple support. They asked for her Apple ID and password, which would have given them access to pretty much everything she has online.

Because of our conversations, my mom hesitated. She patched me into the call and asked the scammer to explain the situation to me. I was very proud that she recognized the scam and knew to ask me for help.

I monitor my mom's accounts

I worked in cybersecurity at Aura, which offers a lot of great products for keeping kids safe online. But my experience with my mom made me realize we were missing a whole vulnerable population: older adults.

I helped develop Trusted Family Access, which allows family members like me to see alerts from their loved ones' accounts, with permission. This gives me peace of mind that I can catch any issues quickly. It's also made other aspects of caregiving easier, like handling medical appointments, because I have access to all my mom's information in one place.

When my mom was scammed, it felt like I was a victim too. I spent hours calling her bank and credit cards to get her money back. If she were to lose her savings, it would impact the whole family. I'm grateful we've found a solution that empowers both of us to keep her finances safe.

This as-told-to essay is based on a conversation with Siobhan MacDermott, a 56-year-old tech founder based in Menlo Park, California. It's been edited for length and clarity.

I've never been underqualified for any job that I've applied to.

I was vice chair at Bank of America and principal at EY. I held senior roles in cybersecurity at AVG and McAfee. I've sat in boardrooms with Fortune 500 CEOs, advised governments, and built practices from scratch.

Then, in early 2024, when I was 54, I had to relocate from New York City to California for family reasons, leaving the management consulting job I'd held as a partner at The Consello Group. I didn't anticipate what could happen when someone tries to re-enter the institutional world in their 50s — particularly as a woman in a career space that doesn't fit neatly into a job description.

The most surprising barrier has been the gap between what I've actually done and what the market knows how to categorize. I'm worried because I'm not sure where the economy is heading, but I'm an absolute eternal optimist.

I'm not going to accept anything other than staying hopeful.

I felt like my job application was going into the ether

It's been frustrating to watch organizations that desperately need exactly what I've built not hire me.

When I started my job search, I reached out to my network to try to figure out what I could do, who'd vouch for me, and where open positions were. A lot of senior roles were being downsized, but I had a lot of people who initially wanted to help me find something.

The strategies that were a complete waste of time were LinkedIn Easy Apply, recruiter calls that went nowhere, and any process that involved a 45-minute competency-based interview with someone who'd never heard of the big companies I've worked for.

I spent the better portion of every day for over a year applying and looking for jobs. I obsessively searched on LinkedIn for new positions, applying over and over again on the site, company websites, emails, and more, but getting nowhere.

I sent out countless résumés and barely got any responses. These are jobs that I know I'm qualified or overqualified to do, but sometimes I didn't even get the courtesy of the automated "thank you for applying" response.

It was like my application went into the ether. I'd try to find the head of HR for these companies on LinkedIn and reach out to them because I wanted the feedback.

I started trying to think of interesting ways to get attention

The strategy that worked the best during my job search was bypassing HR entirely and using direct outreach to CEOs and board members.

I'd send them letters not even related to a job, but more of an observation of their company to get their attention. I tried to be crafty, saying, "Based on my external assessment of your company, here are some things that I think you should be doing as you think through your next quarter."

Reaching out to CEOs got me in the door, but then they'd send me down to somebody who was pretty junior who'd say, "You're overqualified for this job." They'd courtesy interview me because they'd been told to, but it didn't go beyond that.

Sometimes a CEO would send me to HR, and HR would look at my skill set and say, "It doesn't quite match."

That happened quite a few times.

I adjusted my LinkedIn profile to get a better response, and that helped

I changed my gender to male and back to female a bunch of times to see if it made a difference — I didn't change my pronouns, just my actual gender. I felt like I had more responses on LinkedIn being thought to be male than female.

I also think being in Silicon Valley, you age out a lot faster than you do in other parts of the US, and it's definitely a highly male- dominated space. I had those two things working against me from the get-go.

So I removed the first six years of my career from my work experience on LinkedIn, and I took the dates off of my degrees so that people couldn't tell my age. This made me seem seven to 10 years younger, potentially. Once I took those dates off, I felt like I got more engagement on the site.

My job search in Silicon Valley went nowhere, so I decided to pivot and launch my own venture

I started my company out of necessity, and also out of intellectual boredom. I felt like my brain was starting to rot.

It happened about a year into job searching, when I started feeling financial pressure and frustration. I didn't want my full-time job to be looking for a job. My search wasn't looking like it was going anywhere in the foreseeable future, especially out in Silicon Valley. If you're a computer scientist or an engineer, there are jobs available, but I couldn't find a lot out here not in that space.

I started thinking, what am I good at? What do I know? What are all the pieces that I could put together? What problem can I identify that needs to be solved? That came together pretty quickly, and I launched two companies — Khaos Holdings, a strategic risk-intelligence company, and TeenAegis, a child-safety intelligence business, in January.

We're raising capital, and if the capital comes in, that will be the end of my job search. If the capital doesn't come in, then I'll keep searching — but I've decided that whatever I do will be adjacent to the problem I'm trying to solve now.

One good thing came out of the 2 years since my last job

Being out of work for two years shifted my retirement timeline eight to 10 years from digging into savings. However, since my job search started, I've really homed in on what I want to do with the rest of my career.

The journey I went on was a little bit of a midlife crisis. I asked myself, "What's my purpose in life?" as opposed to "What job do I want to have?" and then identified what skill set could bring me to that.

What led me to where I am was really thinking through questions like: What are all the issues that matter to me? What legacy do I want to leave? How do I want to think about my future for the next 10 or 15 years? How do I want to show up every day?

In the beginning, I was going to apply to anything that I could qualify for that would get me some money. Now I'm not going to do that because I don't think that's going to actually be fulfilling or make me happy. My sense of stability has required a deliberate reframe — from "security comes from a salary" to "security comes from what I've built and what I know."

I'm determined to make this work, but I also realize it may not

The hardest thing is maintaining a positive attitude day after day. If my company doesn't work out, then it's not like I can stop trying.

Taking mental health breaks is important because it's overwhelming, lonely, and hard. You lose your sense of self-worth when you're in this position; people look at you like, "Oh, you're the person who's still looking for a job." So it's hard to continue to put yourself out there.

Still, I do believe there's light at the end of the tunnel. It's just the question of how long the tunnel is.

Do you have a story to share about navigating your career in your 50s? If so, please reach out to the editor, Manseen Logan, at mlogan@businessinsider.com.