Day: September 20, 2025

• Ashley Jablow is a career coach who helps mid-career professionals navigate career transitions.
• She says clients may feel stuck due to financial obligations and caregiving responsibilities.
• Her four-step process includes self-discovery, iterative action, and more.

This as-told-to essay is based on a conversation with Ashley Jablow, a 44-year-old career coach based in Richmond, Virginia. It’s been edited for length and clarity.

Most clients come to me because they feel stuck in their careers. They’ve picked up their heads at 30, 40, 50, or beyond and realized that the life and career they chose for themself at 20 no longer fulfills them.

As a career coach who helps mid- and senior-career professionals navigate career transitions, I see that these changes later in life aren’t always as easy as they might be if done earlier. Many of my clients have constraints and existing structures created by financial obligation, caregiving responsibilities, existing careers, and more.

My job is to help people clarify what they want and take actionable steps toward achieving their goals. These are the four steps I take my clients through who want to pivot their career after 40.

Step 1: Discover who you are right now

Although your instincts might be to rage-quit your current job or jump right into solution mode, it’s important to take a step back, open your field of vision, and get curious about who you are at this point in your life.

If asking deep, probing questions like, “Who am I?” is uncomfortable, you simply need to become curious about what topics you’re drawn to — what creates goosebumps and excitement.

I think a lot of mid-career folks don’t spend enough time feeding the fire within them and pursuing things simply because they excite or inspire them.

The purpose of this exercise isn’t to figure out your next career move but to ignite a curiosity and sense of wonder about what makes you who you are. For example, I love stationery supplies like pens, brushes, and notebooks. That doesn’t necessarily mean I should become a stationery designer.

The discovery phase is also about looking outside ourselves and seeing what we’ve missed while existing in our insulated bubbles. For example, look at how the job market has changed and how recent advancements, like AI, might change the opportunities that are available to you.

Step 2: Define your constraints

Next, it’s time to pause and set parameters for the rest of your brainstorming. Consider dealbreakers, criteria for success, and current constraints such as location, salary, time commitment, etc.

Though it may feel like your existing life structures constrain you, I see identifying constraints as a helpful tool for acknowledging your reality and setting criteria accordingly.

Step 3: Imagine your dream life

Using your imagination will be your greatest tool for coming up with creative solutions to your constraints.

This phase is all about being broad and exploratory. We should ask ourselves, “If I had a magic wand, where would I go, and what would my life look like?”

This can involve making a vision board or writing a vivid depiction of your future. Imagination isn’t just for five-year-olds on the playground, and it’s one of the most underutilized tools for creative problem-solving.

Step 4: Iterate to reach your goal

Once you’ve considered your near-term constraints and long-term vision, you might identify a potential goal or area of interest.

For example, a client might decide to quit their job and go to business school. But rather than taking radical action, I’d advise them to consider the smallest, fastest, and cheapest ways they could test if this is a worthwhile decision. This is what I call iterative action.

They could speak to a peer who went to business school and ask them questions about their experience, buy an “Economics for Dummies” book to see if the topics interest them, or even sign up for an online course, like an MBA crash course, to get a sense of what it might be like.

The cool thing about taking iterative action is that the more we take small steps, the more we learn about ourselves, and the less risky a career pivot becomes. We might even find that we’re building confidence in our ability to make good decisions and follow through on our goals.

Do you have a story to tell about changing careers after 40? If so, please reach out to the reporter at tmartinelli@businessinsider.com.

This as-told-to essay is based on a conversation with Mike Plummer, an 81-year-old REI employee in Jacksonville, Florida. Business Insider has verified Plummer’s current employment. He has worked at REI for 13 years. Plummer does not work out of financial necessity, but doesn’t have any plans to retire soon. The following has been edited for length and clarity.

I look back and sometimes think maybe I shouldn’t have left corporate so soon, but I took a buyout, left at 55, and I don’t regret it.

I just turned 81, and in two years, I’ll hit my 15-year mark with REI, a national retail chain that sells outdoor gear and apparel. This is a motivator. My wife is 74 and still works part-time, too. We’re financially in a position where we don’t need to keep working, but we have no real plans to retire fully.

We both get asked a lot, “Why are you still working? You don’t need the money.” But in your 70s and 80s, friends are dying or have medical issues, and you lose that social connection. I work because I have to keep moving, building connections, and engaging with new things.

I’ve been working almost all of my life

When I was about 8, I started helping out at my dad’s convenience store, where we lived in the back. Then, in high school, I worked at a grocery store in the meat market with the butcher, cutting chicken heads. Since I had to pay for college myself, I went as a co-op student and studied engineering.

At my first job, the company would pay for graduate school if I could get in. I got two master’s degrees from New York University, the first in engineering in 1969. But after two years in mechanical engineering, I didn’t think that was going to be my area, so I got my second master’s in operational research in 1971.

I worked in various analytic and management-type roles, and then, in the 1980s, I worked for a couple of years at a startup company. It was a fun time, and it got me interested in the organizational side of business. Starting in 1990, I went to work for a credit card company.

In 1996, I did the same type of program at the credit card company and got a third master’s, this time in organizational development and change from Pepperdine University. I retired as the assistant vice president of training and development in 1999 and left to start working with my wife at her HR consulting company.

My mom inspired me to keep working

After my dad died, my mom was really bored, so she got a job at McDonald’s for about five years in her late 70s.

Besides working with my wife in her consulting business, I also taught a graduate course in organizational development at Webster University from 2005 to 2020. Before REI, I fiddled around with other part-time jobs. I worked for a couple of years at a cruise terminal as a check-in agent because I liked the idea of it, and I was a golf ranger for a year or two.

REI gives employee discounts, and I was motivated at first because I love biking. I started out working on the floor in other departments, but I always wanted to move toward the biking area. I’m now in the action sports department, which includes kayaking, hiking, and biking.

I like interacting with people and stocking and organizing my section. Last year, I won REI’s highest employee honor, the Anderson Award. I worked about 24 hours a week until I cut my hours back two years ago. Now, I only work two days a week, usually from 10 a.m. to 2 p.m.

It helps me stay active and engaged, have a purpose, and connect with friends. I look forward to working at REI with young people and a very diverse group.

When I started, I was the only person over 65 at my store, but now there are about 4 or 5 of us older employees

We call ourselves the Silverbacks. One of the guys is into social connections, and he’s really good at helping young people and mentoring them. One woman is a retired Navy captain who works in the bike shop.

In 2019, I decided to design a survey for my store about joy levels at work on my own. The older people were happier in their jobs and in their lives, and less interested in getting promotions. They had found something that they liked and were good at.

Three years ago, my store manager told me about this author who wrote a book about the secrets of aging well. She encouraged me to see if he could do a talk at our store. Six months later, I got him to do a workshop at four stores in Florida, including ours.

We don’t need my paycheck to keep up with our lifestyle, but I don’t have any plans to retire soon

When I started with REI, I set up a separate account to deposit my earnings. I now make $18 an hour, but when I started, it was only $9 or $10. I made around $7,700 last year, and REI automatically enrolls you in the 401(k) program, which it matches.

I’ll use my paycheck to buy fun stuff from REI or anywhere else. My wife and I both receive pensions from our former employers and Social Security, and take a 4% annual withdrawal from our 30-year 401 (k)s. We expect to continue receiving $40,000 a year from my wife’s HR consulting business until she retires.

My son and I like going to watch horror movies together, and I use my check to pay for those tickets. Now that I’m not making that much since I cut my hours, I’m a little more careful with what I spend.

I’m trying to stick it out for at least two more years to hit the 15-year mark, and maybe more, before I leave REI. My doctor says I’m healthy, but I’m at an age where I could have a major health problem at any time. I enjoy working there, but I’m trying to focus on living the best life I can.

• I went shopping with Dan Ives, the tech bull, outspoken Tesla supporter, and fashion icon.
• Ives said clothing has unintentionally become a part of his brand.
• Between looking at tie-dye and neon sweatshirts, I saw how Ives’ style is mirrored in his stock calls.

When I saw a man walking down Prince Street in canary yellow pants, a bright blue Aviator Nation sweatshirt, custom sneakers, and a hat that said “GOAT,” I knew my wait was over.

I was meeting up with Dan Ives, who isn’t just a well-known tech analyst and major Tesla bull, but also something of a fashion icon. CNBC is used to guys in Brooks Brothers, but when Ives is on, it’s Lilly Pulitzer blazers and lots of hot pink. During our SoHo shopping excursion, Ives didn’t look twice at anything in a neutral tone. My white T-shirt, medium-wash vintage jeans, and simple jewelry quickly started to feel like a bad choice.

Ives ran his hands through button-downs in Faherty, the first store we went to, while explaining that he’s dressed “super different and funky” since he was a kid in Long Island. He eventually landed on a $58 powder blue hat that said “SOHO SURF,” even though he was already wearing a hat and holding another one from where he’d gone to lunch. We walked slowly, Ives swinging the paper shopping bag and occasionally checking stocks or texts on his phone.

Ives told me he tends to wear Vuori or Lululemon at home, and that Aviator Nation is a go-to, but he didn’t take me to any of those places. Instead, he led us farther downtown to Snow Milk, where he recently launched a fashion line. Maybe I shouldn’t have been surprised that our afternoon turned into something of a business opportunity. Ives told me his sense of style is authentic, but it’s also helped boost his brand, especially on social media.

“It’s definitely played a role in the global success, because of the way that I dress,” he told me. “Even people who don’t know my stock calls, they know me as the person who wears the funky shirts on CNBC.”

The brand ties go beyond recognition online and on the street.

Ives is as bullish on tech stocks as he is on clothing. In addition to Tesla, he’s one of Wall Street’s biggest optimists when it comes to mega-cap titans like Apple, Microsoft, Nvidia, and Palantir. Any sell-off in these names is usually followed by a research note from Ives imploring investors to buy the dip.

But his most outspoken moments involve the EV maker. You might remember when Elon Musk told Ives to “shut up” earlier this year, after the Wedbush Securities analyst said Tesla’s board needed to have “oversight on political endeavors.” It was out of character for Ives, who usually gives Tesla an “outperform” rating. (He told me thinks Musk has “pivoted very nicely” since.)

“The way that I cover tech stocks goes to the beat of a different drum,” Ives said of his decadeslong career. “I don’t worry about others, because maybe it’s an unconventional way that I look at names, and I dress similar to how I cover tech.”

Ives thinks people accept his clothing partly because he covers tech companies, not banks. Finance, he said, is way more buttoned up, though he thinks Wall Street is slowly becoming a little bit more casual. Men on Wall Street who are scared to dress “different and funky” will sometimes ask him for advice.

As much as bringing me to Snow Bird might have been a good business move — he was careful to point out his shirt hanging on the wall — it was also a chance for me to see Ives in his element. Jamie, a Snow Bird employee who worked on the brand collaboration, had picked out blazers to try on, and Ives reached for a New York-themed gray number. When Jamie started to say it might not fit over his sweatshirt, Ives, very politely, set him straight.

“That’s part of the look,” he said. Ives ran his fingers over baby pink and tie-dye sweatshirts. He tossed around the words, “Oh, that’s so cool,” about piece after piece. My white T-shirt and I slowly faded into the background.

I tried asking Ives about what tech stocks he finds most exciting just as Jamie handed him mint green and lilac hats, but I’m not sure he heard me.

“Dude, that thing is sick!” he said instead.

• Jennifer Jamali, 34, felt isolated in her suburban Austin neighborhood.
• In May, she, her husband, and their daughter moved to Bogotá, Colombia, to be closer to family.
• In Bogotá, they live rent-free, pay $300 a month for day care, and earn thousands renting out their Austin home.

This as-told-to essay is based on a conversation with Jennifer Jamali, a 34-year-old who moved from Austin to Bogotá, Colombia, in May. The conversation has been edited for length and clarity.

I grew up in Houston but had been living in Austin for nine years. I felt stuck in my suburban neighborhood. Everything looked the same, it was very quiet, and you barely saw anyone outside.

A typical day involved going to the gym or getting coffee and then returning home to work with my husband. I felt isolated and craved more adventure and community.

In 2022, I was laid off from my job as a tech recruiter at Spotify while eight weeks pregnant. Work had been slow leading up to the layoff, so I wasn’t surprised, and luckily, I was financially prepared.

After that, I started my own business as a money and career coach. But even then, life felt mundane. Every day was the same: I took my daughter to day care, worked, and then picked her up — the same thing, just a different day.

In 2025, we lost multiple family members and were going through grief. That’s when it clicked for me. Life is so short — why are we spending so much money in the US for a life we’re not even happy with?

In May, we decided to move to Bogotá, Colombia, where my husband is from, and where his family still lives.

Bogotá has a warm, human-first culture. My days are full of microconnections where I say hi to my neighbors, and they actually acknowledge me. I feel like I have a real community here — and I am lucky to be a part of it.

The US dollar also goes very far in Colombia. Our monthly living expenses have dropped from $7,000 in Austin to $2,000 in Bogotá. Sometimes, I wonder how we did not move sooner.

There’s a stronger sense of community in Colombia

We live in central Bogotá, which is like the New York City of Colombia. It’s dense, walkable, and has parks everywhere. It’s growing fast, too. Many of the original houses are being demolished to build large apartment buildings.

We live in a quiet, walkable neighborhood about two blocks away from my in-laws. We see them almost every day. They babysit when we need help, like right now, when we’re sick and they’re watching my daughter. We love having their support.

We live rent-free in an apartment unit that my in-laws invested in — we definitely know that’s a privilege.

The apartment is about 900 square feet, much smaller than the 1,800-square-foot, four-bedroom home we lived in Austin. We definitely downsized, and I do miss my backyard occasionally. But living here, I realize we don’t need all that space.

A lot of the apartments in Bogotá are small because the culture here isn’t really meant for staying at home. Everyone here lives an active lifestyle; they’re always outside and moving, and no one sits around and watches TV all day.

In Bogotá, I get 10,000 steps daily just by going to markets and walking my daughter to school.

I have a very young baby, and sending her to school in the US terrified me. Here, it almost feels like a fantasy. Her teachers are really diverse, and they seem to really care for her. The day care also has a chef on-site who makes them homemade meals every day.

With the support from my in-laws and the safety I feel here, I’ve been thriving in Bogotá. It’s helped my mental health and my life in so many ways.

We’re saving a lot of money on childcare

We have extremely affordable childcare in Bogotá, and healthcare, where doctors come to my home, and it’s included in our monthly payment.

My husband and my daughter are on the healthcare system here, which costs us $120 a month. I’m still not on the healthcare system, but for a doctor to come to our home and give me prescriptions, it’s only $35.

The biggest reduction in our monthly expenses has been in childcare: day care went from $1,200 a month to $300.

We’re also saving on groceries. For example, I can buy a 30-pack of eggs for $4. There are markets everywhere, too. We don’t go on a monthly grocery haul; instead, we get fresh fruit and vegetables for the day and re-up if we need more.

Housing has also had a huge impact on our finances. While we live in Colombia, we rent out the home in Austin on Airbnb and VRBO as a mid-term rental (30 days plus). It’s been booked solid since July. Our current renter is staying from August to October, and we’ve earned nearly $4,000 from their stay.

I think keeping the house is a good investment. We purchased it in 2016 for $228,000 and have a monthly mortgage of around $2,000. We’ve owned it for almost 10 years, and it has a great mortgage rate. Plus, we have a lot of equity in it.

I’m less stressed in Colombia

The pace of life in Colombia is much slower, and I’ve learned to appreciate it. It has made me a lot more present and patient.

My in-laws have a house in the mountains. We go there for a week at a time, and I feel more at ease and creative there. It’s where I create all my LinkedIn content.

Because stressors don’t block my creativity, I’ve been able to grow my businesses. In addition to coaching, I also work with social media influencers to develop brand partnerships.

I don’t plan on moving back to the US. I don’t miss the rush, the noise, or the division. Life in Colombia is way less stressful. I feel more connected to my community and like I’m at home.

When I asked Ciara what motivated her to start taking even better care of her health, I was struck by her answer.

“I just pray that I can be on this Earth for a long time, to witness a lot of beautiful moments that my kids are going to experience, and with Russ,” the 39-year-old singer and record label CEO said emphatically over Zoom, referring to her NFL quarterback husband, Russell Wilson, and the blended family’s four young children.

Sure, most people would say they look after their health to live longer (and, let’s be honest, stay cute). But the way Ciara describes it — looking seriously into the distance, her flawless platinum blonde hair contrasting with her quietly luxurious black track jacket — it seems as if she really, really means it.

Ciara’s combination of intense enthusiasm and sincerity is the same as we speak about topics as varied as pizza, taking a bath, and sitting on her porch in New York City. She and Wilson, 36, relocated to New York City after the quarterback joined the New York Giants earlier this year.

This ability to make anything she turns her attention to thrilling is part of the special sauce that has kept her relevant since 2004, when, at age 18, she released her quadruple platinum debut album “Goodies.” That sauce also drips onto her signature sticatto dance moves and when she smoulders powerfully onstage and in music videos, most recently for her latest album, “CiCi,” released back in August.

Now, Ciara’s day-to-day is about trying to keep doing those things she loves for as long as possible. She shared how she spends the hours she’s not working in Business Insider’s 5-9 series, as part of her partnership with the creatine company, Thorne.

Organizing chaos

You exude this fun, self-assured, yet positive and calm vibe. How do you maintain that while juggling a busy career and raising four kids? Is it morning rituals, clever scheduling, or leaning on your village?

First of all, you’re so kind, and it’s a combination of all of the above. There’s definitely no “I” in team, and my life is what I call organized chaos — all good chaos, but it’s chaos.

Having a schedule is a game changer and gives me clarity in the midst of the chaos, even down to scheduling my free time. Sometimes I write down “2 p.m. to 4 p.m.: time with babies” or whatever it may be.

That sounds very helpful. What do you have for breakfast? Do you have a goal in mind?

It depends. Sometimes I have a more intense regimen because I’m preparing for something like a red carpet or a performance. And when I’m in that zone, I’m really mindful of what I consume.

I like to kick off my day with creatine because I need that energy boost. I need that support for my cognitive functioning.

How has your morning routine changed over the years? Is longevity and aging well a priority for you right now?

When it comes to health, you have to be looking ahead. I’ve always been a little bit curious about health and pretty tapped in, but I just started to create a strong desire for being intentional about my health.

As you get older, you crave things that are going to only help you get better. I have good muscle memory, but I can’t rely on that forever.

I want to be more intentional with what I’m feeding my body: doing my best to make better health choices.

What I’ve learned, from my trainers to close friends who take great care of themselves, is that you’ve got to start work early versus trying to do it when things start to creep up on you.

Staying consistent with healthy habits

What was the catalyst for you to level up your health?

The mom in me thinks a little deeper about everything. I just pray that I can be on this Earth for a long time to witness a lot of beautiful moments that my kids are going to experience, and with Russ. I love life, I really do, and I like making the best of life. That’s one of my goals: living life to the fullest.

I feel so blessed to wake up to the love of my life every day. I feel so blessed to do things that we get to do together. It’s just my pure desire to do those things, and also I just want to take care of me.

How do you make time for movement? Are you into intense workouts or more chilled practices like yoga? You always seem so upbeat!

I think you got the right idea, Kashmira. I’m an energy kind of girl. Russ and I definitely train together whenever we can; it’s always so much fun.

When I train, I definitely love the energy to be high. I’m not so much of a yoga girl like that. Will I do yoga? Yeah, but I like to keep the energy going and flowing.

What do you do when you work out? Pilates? Boxing? HIIT?

It’s a combination of everything. I actually haven’t boxed in a while, but I do love boxing. Rehearsals, that’s another great way to work out. I love dancing, obviously, that’s a big part of my identity, and it’s a big part of my jam. I love when I learn a routine and then come back a little more snatched.

I love taking jogs in the street too, especially here in New York. It’s fun to run out here in these beautiful streets and see all the buildings, the people, the vibrant energy that just radiates from the streets. It’s so cool. It’s like running in a movie every day.

Yes, I used to run in London along the river, and I was like, “Wow, I’m the main character of this film.”

Yeah, right. It’s really cool.

Tasting the Big Apple

As you wind down for the day, how does dinnertime work in your household?

We love food. One of our great connecting moments is when the family sits down and eats together, or our date nights.

Russ is getting ready for football right now, so he’s a bit more conscious of his choices to stay lean for the field.

Sometimes I’ll join him on that journey, and sometimes, I’m like, “You do that chicken breast, and I’ll do this pizza.”

We kind of go based off what we’re feeling, but everything in moderation is the ultimate thing. Even with our kids and treats: they love their candy, they love their desserts, but it’s like, “OK, let’s do it in moderation.”

How do you decide where you go for date nights? Are you rolling a dice to see whether you’re eating takeout on the sofa or getting dressed up?

We both put options out there, but Russ does so much better than me picking what we’re going to do. I’m just like, “Babe, you do it.”

Romance me!

Well, he’s naturally so romantic, so I just trust him. He’s got it. If he picks it, it’s going to be great. He’s 10 for 10 with the restaurant choices. And again, we love our food, so we tag team.

How else do you spend your evenings? I have this image of you sitting with Missy Elliot and Normani drinking cocktails.

It depends. In New York, you have so many options. It could be a date night, it could be me and my girls getting together for a meal. That’s always fun.

Sometimes I just sit on my back porch and just look at the city or listen to the city. I love that. The sound of the city is like music. It’s very peaceful.

They say New York is the city that never sleeps, but when the city does actually sleep, it’s a really beautiful sound and view. Nothing beats it.

Even something as simple as sitting in the bathtub is a game changer. Sometimes the simplest things have the biggest impact.

Fake photos. False claims. Wild conspiracy theories.

Former federal agents fear the potential for other would-be assassins to seek out widely available, decades-old firearms that require only basic proficiency to hit distant targets.