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• For Love & Money is a column from Business Insider answering your relationship and money questions.
• This week, a reader wants a portion of their inheritance now, rather than after their parents die.
• Our columnist says it's OK to ask, but that it's important to be self-aware and approach thoughtfully.

Dear For Love & Money,

I am lucky enough to come from a family with a lot of generational wealth. My great-grandparents passed down a large fortune to their kids, who passed it down to my parents when they died.

Before their deaths, my grandparents also used a large part of it to make their children's and grandchildren's lives better. They gave my parents enough to pay off most of their house, paid for my college, bought me my first car, and did the same for my sister and cousins.

Now, my parents have their share of the family inheritance. My sister and I fully expected our parents to follow our grandparents' example and give us some money up front — not the whole inheritance, but enough to help us pay off some debt and make our lives a little easier.

My parents have shown no signs of giving us a penny right now. I am sure they intend to leave it to us when they die, but until then, it doesn't seem to have even occurred to them to bless their children and grandchildren the way their parents did.

My niece will begin college next year, and my sister has dropped several hints. My wife says I need to just come out and ask them for some of the money because we could use the cash, but the idea of doing that makes me really uncomfortable. What do I do?

Sincerely,

Possibly Presumptuous

Dear Possibly,

If you are presumptuous — and perhaps you are — you have every reason to be. A large inheritance, it seems, is a family tradition (you lucky thing). Traditions are typified by the rituals that accompany them. In your family, this has looked like the bulk of the cash going to the next generation as a traditional inheritance, with a tidy sum set aside to ease the way for all direct descendants in the form of an early inheritance.

As such, it makes sense that you would have those expectations. However, no family tradition happens automatically, and each new generation must determine which parts of the legacy to leave and which to keep. In your case, this decision belongs to your parents.

I agree with your wife that asking directly is your only option for an advance inheritance payment. After all, your sister has already tried the heavy hinting method, and while you refer to it as "generational wealth" and "family inheritance," the money is your parents'.

Before you talk to them, however, I suggest you examine your motives first. There are two different types of entitlement: justified and absurd. Justified entitlement looks like someone driving to pick up their paycheck after working all week. Absurd entitlement looks like an adult racking up a credit card on a luxury vacation and then expecting their parents to pay it because they raised them to enjoy that lifestyle.

Based on your letter, I would guess your entitlement is justified — or at the very least, understandable. There is nothing wrong with having expectations because your family has always done something a specific way. However, the justified entitlement begins veering into the realm of the absurd if you feel resentment toward your family for not giving you something that isn't yours.

Self-awareness in this regard is crucial for personal growth. When I called you lucky at the beginning of this letter, I meant it. I, like most people, don't have an inheritance to look forward to, to help pay off my mortgage or send my kids to college. You hit the generational wealth lottery just by being born into the right family, as did your parents. I don't say this as a jealous sneer, but as a reminder.

You don't need to bow your head in shame for lucking out, but you must remember this money is a gift. Nobody likes the kid screaming at the tree on December 22nd because they want to open their presents early.

Not being that person is really a matter of tone. If your parents sense you're upset with them for even having to ask, they will be understandably hurt, which will only break down your dynamic. If you come to them with gratitude, humility, and curiosity, they might remember when they were in your shoes.

I mention curiosity because your parents may have hopes and expectations for this inheritance of their own. I can only imagine they had years to plan what they would do with it when it was finally their turn. Ask them about it. Show them your intention isn't to leapfrog over their moment holding the generational wealth, but to honor it.

Not only does this eliminate any ideas of absurd entitlement they may see around your request, but it might also help them see an early inheritance to you and your sister as a kind of collaboration — and the money as a family business. For now, they are co-CEOs and get to call the shots, but you, your sister, and your children are the future and worth the investment.

That said, I wouldn't shy away from reminding your dad that his parents did the same for him. I wouldn't make this reminder heavy-handed or accusatory. Instead, it should be a gentle way to introduce your request. Start by saying something like, "Hey, Dad. Remember how Grandma and Grandpa gave you part of your inheritance even while they were still living? I was thinking…"

You'll want to prepare a well-thought-out financial plan. Research investment options, savings accounts, and trusts, and determine how to maximize the financial gift you're requesting. Then, pitch this plan to your parents.

Whether your parents are holding onto the inheritance tightly because they still see you and your sister as fiscally irresponsible teenagers, because they have personal retirement concerns or priorities, or because they just didn't think you needed the money in the moment, presenting them with a plan is a great way to inspire their confidence and show them that giving you the money is not a risky indulgence, but a sound choice.

Your letter describes a lineage of security — not only the financial kind, but the kind that only happens when each generation looks after the next. While your parents may be playing with the timeline a bit, you mentioned having little doubt that they will leave the money to you and your sister when they die. This tells me your family looks out for one another. No matter how this conversation goes, take comfort in that security. That's the kind of wealth that can't be spent in a single generation, and you've got it. You lucky thing!

Rooting for you,

For Love & Money

An earlier version of this article was originally published in September 2024.

Looking for advice on how your savings, debt, or another financial challenge is affecting your relationships? Write to For Love & Money using this Google form.

This as-told-to essay is based on a conversation with O'Shea Jackson, known professionally as Ice Cube, a 57-year-old rapper, actor, and cofounder of the professional three-on-three basketball league Big3, who is based in Los Angeles. The following has been edited for length and clarity.

I started out wanting to be the best rapper in the world. Then John Singleton put me in "Boyz n the Hood" in 1991, and I loved creating at that level. I didn't just want to be an actor; I wanted to be a producer and a writer. I wanted to control my own films and be involved in record company meetings. That thrust me into the business world.

I understand, from the neighborhood I come from in South Central Los Angeles, that if you don't learn the game, you're going to get taken advantage of. I knew that if I really wanted to be a solo artist and didn't want to be a horror story at the end of my career, I needed to learn the business. That's when I started transitioning to working behind the scenes.

In 2016, my cofounder, Jeff Kwatinetz, and I had the idea to start a professional three-on-three basketball league. We spent a year throwing around ideas for it before announcing Big3 in January 2017.

I love three-on-three, and I've always wondered why it hasn't been professionalized. We wanted to elevate it and attract players who still want to play at a high level against their peers in the summer. I also still rap and act, and I haven't looked back.

Here's a day in my life in Los Angeles.

5 a.m. — my goldendoodle wakes me up

My goldendoodle, Luffy, and I wake up at the same time, or one of us wakes the other up. He's a year old, so he's still got puppy energy. My wife, Kimberly, and my four kids watch an anime where the lead character's name is Luffy, which is how he got the name.

I've been an early riser ever since I was young. I like to wake up before everybody — sometimes two hours before my family — to hyper-focus on anything that needs my undivided attention. The East Coast is three hours ahead of us anyway, so I don't want to be late talking to people there.

7 .a.m. — coffee and walking Luffy

I usually make myself coffee at home. I'm a fan of Peet's dark roast. Then I take Luffy for a walk.

I'm not big on working out early in the morning, so I try to exercise in the evenings. To me, the morning is for coffee, enjoying being alive, and being happy that I get another chance to see another day.

I'm not a big breakfast guy, so I usually don't eat until late afternoon.

8 a.m. — thinking in the shower

Most of my ideas come when I'm in the shower. They'll just flood me with everything I need to get done, almost in order: you gotta have that, you gotta have that, stop procrastinating on this, get to that. The shower is where I get a lot of my clarity.

9 .a.m. — prioritizing my schedule from my home studio and office

I don't go into the office — I stopped doing that in 1999. I'm not built to be in the office. I'm a remote kind of guy.

I've got a spot in my house that's a studio and office. A lot of work gets done in there, including new music. It's cool to have it all in one place.

Because I'm splitting my time between Big3, music, films, and other things, I have to really plan the day and prioritize. There are things that have to get done today and things that can wait until tomorrow, so it's about deciphering what needs my immediate attention and focus.

10 a.m. — meetings focused on wherever I am

When I'm traveling, my day can vary a lot. I have a lot of meetings on my iPhone and Zoom, so I plan them around whatever I'm there to do.

If I'm on tour, everything has to come after what I have to do that night and the focus I need to give to the live performance. I've tried to do a movie in the daytime and go to the studio at night, and something suffers.

You don't want to spread the work too thin, either, just because you can. You want everything to still be as top-notch and good as you can make it. That takes discipline.

12 p.m. — ordering lunch and trying not to succumb to burgers

When it's time to eat, the first thing that pops into my head is always burgers. I try to push burgers aside and think of something different, like a Greek salad wrap. Otherwise, I'd go for burgers and fries all the time.

1 p.m. — checking out social media and executing on projects

I look at a lot of social media to figure out my next move. Social media-wise, I still like X, Instagram, YouTube, and TikTok. I'm not a big-time Facebook guy. I also don't use any AI apps.

I have several projects, and they're each in one of three stages: planning, execution, and follow-through. There's always work to be done. I've been in business for 40 years — I've seen it all. Nothing gets me too high, and nothing gets me too low.

I'm always looking for the most strategic way out of a sticky, complicated, or bad day. I don't really let it stress me, because I always know there's a solution.

6:30 p.m. — shut down business and hang with my family

It's crazy for somebody in the music industry, where mostly everything happens late at night, but it's for my sanity.

When it comes to my off time, people think I'd be out enjoying being Ice Cube, running around and getting the love that's out there, but I like kicking it with my family, hanging out, and not doing too much. A typical dinner is going to a steakhouse with my family, or to a burger joint if I'm on the road.

To unwind, I like to watch sports. Hopefully, there's a game on that I want to see: basketball, football, a Big3 game, or baseball. I'm a Dodgers guy.

11 p.m. — try to get to bed

I don't like to talk about stuff late at night, because then I'll be up all night, and I have to be back up in a few hours. I don't need much sleep, about five or six hours, but I make sure I get it.

Some days, I'm off to do something super cool, like a concert or a movie in France. It's important to balance the craziness with the regular, sensible stuff.

My life can be very exciting and complicated at times, and very simple and normal at other times. It's the best of both worlds.

• Kate McNeil opened All the Tropes, a romance bookstore, six weeks after quitting her job.
• Despite concerns about market saturation, All the Tropes thrives as a niche community destination.
• Passion, perseverance, and local support helped McNeil launch her business.

This as-told-to essay is based on a conversation with Kate McNeil, a 41-year-old small-business owner based in Atlanta. It's been edited for length and clarity.

The idea to open a romance bookstore started during COVID.

I joined an online group of fellow romantasy readers, looking to connect with other people who also enjoyed my favorite form of escapism. That group had over 2,000 members, and it was difficult to feel a sense of community. Eventually, it broke off into local chapters.

After COVID, I didn't know of any dedicated space for these same readers to meet in Atlanta. That's how I started the journey to opening the first romance bookstore in my neighborhood. In the two years since I opened, more romance bookstores have opened up, including one less than two miles away.

I thought I'd retire from my teaching job

When I launched All the Tropes bookstore, I was working a job I thought I'd retire from. I taught theater at Decatur High School for six years. My students always came first. I didn't want those kids to feel like I wasn't present or that they didn't have my undivided attention, so the bookstore was a back-burner idea for a few years.

I'd get home from rehearsal at 11 p.m., conduct business research until 2 a.m., then get up at 6 a.m. and go to work the next day and teach.

I took my time to gain a full understanding of the market, but there were still challenges

I learned about dealing with publishing companies and book distributors, connected with local artists to showcase their work, and reached out to local authors. One of the biggest challenges was finding a place for the store.

I knew that I wanted to stay on the east side of Atlanta because I lived in Kirkwood and felt very connected to the community.

In 2024, I found a location a four-minute walk from my home, and I knew it was time to make my idea a reality. In May of that year, I quit my teaching job and prepared to open the bookstore by the end of summer on Romance Bookstore Day.

I had 6 weeks to get the store ready for opening day

I received the keys to the bookstore six weeks before the day I planned to open. The timeline I had for opening day came with a lot of risks. I had cashed in my retirement fund, quit my job, and had a large preorder of "Onyx Storm" before there were bookshelves in the store.

There were many times my friends and I didn't leave the store until 4 a.m. A local artist painted the shop; I printed my merchandise at a local shop in Kirkwood; and I created the fabric wall. There were many nights I had doubts that All the Tropes would come to fruition.

I was a mom with two young kids opening a niche business that, to my knowledge, would be the first in the state, but I was prepared. I had my accounts with publishers, and my branding was complete. Perseverance, my husband, my village of friends, and an invested community got me to opening day.

All the Tropes opened August 17, 2024, on Romance Bookstore Day. In the span of a few months, I went from a passionate high school teacher to the owner and operator of a romance bookstore.

An increase in niche romance bookstores in the city concerns me

Even in a city like Atlanta with several thriving independent bookstores, I wonder about the percentage of residents who read for fun and, more specifically, read romance. While becoming a general indie bookstore would allow me to sell so many other things, I still believe All the Tropes can continue to thrive in a niche market, despite oversaturation.

Unlike a large book retailer, All the Tropes is a destination spot people can come from out of town to visit. Our social presence and promotion of local writers and artists also offer something unique to readers.

All the Tropes could pivot to general fiction, but so far, more stores opening has not impacted store traffic or sales.

4 Things helped me turn my business idea into a reality

All the Tropes continues to thrive because of my original vision of creating a community space for romance book lovers to connect. We now have eight active book clubs and continue to see consistent revenue.

Passion, trusting my gut, therapy, and a supportive group of friends are the reason I was able to turn an idea I brainstormed late at night into a successful niche business ready to grow.

We are now ready for a larger space and to expand our three-person team.

Do you have a unique small business story to share? Email the editor, Manseen Logan, at mlogan@businessinsider.com.

This as-told-to essay is based on a conversation with Jeff Kinney, the 55-year-old author of the "Diary of a Wimpy Kid" series, who lives in Plainville, Massachusetts. It has been edited for length and clarity.

When I wrote "Diary of a Wimpy Kid," I worked on it for eight or nine years without thinking I was writing a book for kids.

I thought I was writing a book for grown-ups that would feel like "The Wonder Years" or "A Christmas Story" — looking back on childhood through the lens of an adult.

The first thing that surprised me was that my publisher said I'd actually written a children's series; it caused a lot of cognitive dissonance.

But what also surprised me was that kids understood the irony in the books. They understand that Greg is an unreliable narrator; they seem to get the joke.

After writing the series, and after raising two kids of my own — ages 21 and 23 — I've learned a few things about kids. Here's my best advice about getting kids to read, screen time, and more — plus a few things I'd go back and change if I could.

1. To get kids to read, feed their interests

I recently heard author Jack Gantos say that after dinner, he and his family would get out their books and read. I think that's really cool and also very old-fashioned, in a way. I wish we'd done it when raising our kids.

With reading, I think the most important thing you can do is feed your kids' interests, whether they're interested in Pokémon cards or sharks or tornadoes. Get them books or magazines that speak to their interests, rather than trying to give them books that we read as kids or books that are too high-minded for their age level.

A lot of authors who write for kids start with some sort of a lesson, and there's a time and place for that. But kids read for the same reason that adults read: to be entertained. If we start from a position of trying to teach kids a lesson, they'll sniff that out and turn away from it.

It's really important to encourage kids down a path that gets them reaching for the next book. I want them to feel a feeling of success in having finished a book because that's an important act of completion. But mostly, I'd like them to keep reading, whatever form that might take.

2. Listen to them

In everyday parenting, sitting at dinner with our kids and hearing about their day without judgment is a really good foundation. Just about everything that kids today are going through, we've been through in some form. The most powerful thing that we can say to kids is "I understand," or "I've been there myself," and share stories, making sure that they feel seen and heard.

As parents, we should make ourselves vulnerable to our kids by telling them about the struggles that we went through.

If we do that without moralizing and without judgment, I think it draws us closer to our kids and turns us into a resource for them.

3. Envision your future relationship

I've always thought about my relationship with my kids by imagining, How do I want our relationship to look when my kids are adults? I've tried to anticipate that and treat my kids that way the whole time.

I think it's working out because my kids will call me and want to go see the Patriots or the Celtics with me. I think that's partially because I've always had this version of our relationship in mind.

4. Don't get too wrapped up in kids' sports

As parents, we live and die by our kids' successes in sports. I certainly got too caught up in it and couldn't really anticipate that there would be a life beyond sports for my kids.

If I were to go back in time, I probably would change my approach on that. We like to see our kids succeed, and of course, sports is a big stage where there's a lot wrapped up in their success, including social issues and self-esteem.

When our kids are thriving, we feel really good for them, and when they're failing, it's tough for them and us. I can understand why that happens with parents, but I can also see that it's good to take a step back.

5. Help them understand that social media manipulates

Social media bullying is something that we never had to face growing up, and it's really unfortunate and damaging.

Screen time has changed things — you see studies finding that kids are dating a lot less, and there's a loneliness epidemic.

As parents, we can help kids by educating them and helping them understand that social media companies are incentivized to make you spend more time on your screens. The more that my kids, who grew up immersed in the social media world, began to understand that, the more they wanted to move away from it.

They get out there in the world — touch grass, play sports, and pick up basketball. My son will put lockouts on his social media.

It's important for us to think for ourselves before we turn to AI

As AI becomes a part of schoolwork and daily life, my concern is that AI makes a lot of things very easy.

At times, I look for solutions through AI that I could conjure up myself, so I worry about how that rewires the brain when you feel like there's always an agent that can solve your problem for you. It could reduce your own capacity for problem-solving.

It's really important for kids to be able to think for themselves before turning to the tool.

To counteract that, getting out in the world and interacting with one another is really important. Put kids into social situations; for example, my son has been working as a bookseller this past year, where he's had to interact with lots of different types of people and solve problems.

A lot of kids or young people in this generation are more isolated. They spend a lot more time in their rooms on their phones, and so I think that getting them out there interacting with other human beings is going to give them a competitive advantage.

• Danielle Fewings, founder of Get Clear Beauty, has invested in cosmetic treatments since she was 27.
• Fewings' journey with aesthetic procedures began with a breast reduction and includes Botox and filler.
• Her $150,000 investment in herself has supported both personal confidence and professional success.

This as-told-to essay is based on a conversation with Danielle Fewings, a 40-year-old entrepreneur from New York City. The following has been edited for length and clarity.

I started my career in digital marketing and ran my own agency from 2020 until 2025, when I sold it. I'm now the founder of Get Clear Beauty, an aesthetic treatment marketplace, which I started in 2026.

I've always felt like there was something missing from my appearance, as if someone much more confident was buried beneath it all. I got my first procedure done in 2013 and have had many since.

I don't regret any of them.

I'm the most treatment‑forward person in almost every room I'm in

In my broader New York circle, routine maintenance is completely normal. People are getting Botox and lip filler, and a few have had breast augmentations. Most are dipping in rather than going all in.

I'm honestly the most treatment-forward person in almost every room I'm in. In any given conversation, I'm the one who's had the most work done, which is a little wild when I think about it.

For most of the people I know, the max is Botox. Routine maintenance is common around me, but no one I'm close to has done anywhere near as much as I have.

My first major decision was my breast reduction at 27

I wore a 32G and desperately wanted them smaller. I call this my gateway surgery because it was honestly a very easy recovery, so I had this ease as the template, which gave me the confidence to keep pursuing additional treatments.

It made me more willing to put myself out there, both in dating and especially in showing up online to create content for my business, which matters enormously when you're building something. It shifted how I approach relationships, too, both friendships and romantic ones.

When you feel confident inside and out, you see yourself as more valuable, recognize your worth, and become more selective about who you let into your life. As I've felt better about myself, I've been more intentional about the relationships I keep close, and I see a direct correlation between the two.

I've never made decisions due to outside pressure

My choices have always been personal. I've never done any of this for another person or because of outside pressure. It has always been about putting my best self forward, and if that takes some tweaks and some money, I'm willing to do it.

I'm a very confident person — I just haven't accepted every imperfection. My upper blepharoplasty is a good example: most people would say I didn't need it, and they would be right, because no one needs any of these things. I wanted it. My eyelids felt heavy, and I chose to change that.

I'm fully committed to antiaging and the maintenance it requires. I go to my quarterly Botox appointments and my annual lip filler appointments, and I'll be ready for a facelift when that time comes. The idea that aging gracefully means avoiding treatments is absurd; aging gracefully is doing whatever feels good to you as an individual.

The cost breakdown

Because my first breast surgery was a reduction, I paid $6,000 out of pocket, and my insurance covered the rest. I had a full-body makeover in the Dominican Republic, which included a tummy tuck, skin tightening, and two further breast surgeries after major weight loss, costing around $12,000. I've also had liposuction, scar revision, an upper blepharoplasty, Sculptra and filler, a Morpheus8 treatment on my legs, tattoo removal, lip blushing, microblading and shading, Invisalign, and teeth whitening. These procedures have cost about $50,000 in total.

The maintenance I keep up with regularly includes manicures and pedicures, which I have gotten every two weeks for the past 10 years; lash extensions, which I have gotten every three weeks for about 15 years; Botox; more filler; peels and lasers; tanning; and haircuts. The recurring maintenance has cost about $105,000 over time.

What struck me is that the one-time procedures come to about $50,000, but the quiet, recurring maintenance is over $100,000. The costs nobody tracks are the ones that add up the most. That is exactly why I built Get Clear Beauty.

Each procedure served a purpose

My whole philosophy has been doing high-maintenance things to stay low-maintenance. The lashes, manicures and pedicures, lip blushing, and microblading are all upkeep that let me feel put-together with minimal effort, and because of them, I barely wear makeup, so some of that cost is a trade-off.

The bigger procedures came from real changes in my body. My weight has gone up and down for years, and that has driven a lot of it. The Morpheus8 on my legs was for skin laxity, because I'm not ready for a leg lift and probably don't need one. I've had three breast surgeries total.

I'd never do CoolSculpting, and I'd never have a nose job. I don't think CoolSculpting is cost-effective, and I've grown to love my nose.

My appearance impacts confidence, and confidence impacts business

When you're on 15 Zooms a week and constantly recording content to win business, looking and feeling your best matters.

Appearance affects business outcomes, but for me, it works through confidence. When I feel good about how I'm showing up, I represent my company more powerfully and carry my knowledge into the room in a way that lands.

I love how I look. 10 years ago, I never thought looking this way was achievable, and it's the result of a GLP-1 medication, surgeries, and really taking my appearance by the horns. I'm in a genuinely happy place with it.

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.

• Tiffany Tang founded DrinkFolks after a transformative journey across Asia in 2023 and 2024.
• Tang's layoff in 2023 led her to Bali, where she decided to extend her 30-day trip to over a year.
• DrinkFolks, inspired by Tang's travels, supports women-led farms and brings jamu to the US market.

This as-told-to essay is based on a conversation with Tiffany Tang, the 30-year-old founder of DrinkFolks. It has been edited for length and clarity.

I'm the founder and CEO of DrinkFolks, which brings jamu, a 1,300-year-old Indonesian herbal remedy, to the US as a prebiotic root tonic.

For the first two years of my career, I was an assistant director at a gallery owned by the first female fine arts dealer in America. From 2017 to 2021, I worked at Christie's International Real Estate in marketing and communications roles.

For the next year, I was a senior communications manager at CSM Sport & Entertainment before taking on a similar role at a fintech company that helped millions of Americans sustainably build their credit scores through rewards.

I felt positively about that job, but I was laid off in May 2023

I was grateful to work there. We were doing big things, and I really learned what it was like to be at a mission-driven company.

The most interesting thing about my layoff was how incredibly calm I felt upon hearing the news. Our CMO told me first, and she was a friend, my college professor, and an executive I admire and respect.

When she told me, I said I didn't blame her, and this was a time for a reset. Turns out, the layoff was the best thing that could've ever happened to me.

A few weeks after my layoff, I booked a one-way ticket to Bali

For a long time, my self-worth was my net worth — my title, my salary, my career trajectory. When the layoff hit, I lost my sense of self. Reflecting afterward, all I could think was: who am I without the high-paying job?

A few weeks earlier, I had watched the movie "Eat, Pray, Love." When the layoff came, something in me said that this was my moment. I opened Kayak, found a one-way ticket to Bali for around $1,000, and booked it. Bali felt approachable and warm.

What was supposed to be a 30-day reset changed the course of my life

I originally planned to travel in Southeast Asia for a month but ended up staying from June 2023 through August 2024.

My awakening happened on day three. One of the first things I did in Bali was a Panchakarma, a full-body Ayurvedic detox at a retreat in Ubud. There was an optional silent day; one of the first times in my life I rooted and looked inward.

Sitting with my journal, I knew I had to stay. I was still negotiating my severance, so I did the math: my savings, my investments, what each month would cost. When my severance came through a few weeks later, it jump-started the journey.

The deeper turning point was Hong Kong

Everyone I met understood me on an indescribable level. It was the only time in my life I was speaking Cantonese to people outside my family, reconnecting with my heritage. By the time I came home for the holidays, I had decided: I was moving to Asia.

The spark for the company was the women I met. Across Indonesia and Southeast Asia, I sat with women quietly building something of their own. I wanted to help these women build generational wealth for their families. I built DrinkFolks as a way to sustainably invest in them — 3% of every sale goes to women-led farms and nonprofits across Southeast Asia through our FolksFund — while supporting health stateside by bringing ancient wisdom into people's homes.

I started the company in January 2024, took every jamu class I could find in Bali, visited the source of jamu in Yogyakarta, and reformulated recipes in my Hong Kong kitchen.

By October 2024, I was back in the US, working with California food scientists to scale up my home-tested recipe. We launched in NYC in October 2025. Today, we're in 70+ stores across the US.

Living in Southeast Asia made the math work

My salary before the layoff was $160,000 a year, plus equity. When I set off, I had roughly $14,000 between savings and severance — my spreadsheet calculated 4.6 months of runway — and I felt comfortable investing that in myself.

I budgeted like it was my job. I tracked my actual spending obsessively for the first four and a half months and came in at roughly $7,700 total.

All-in, I averaged about $1,300 to $2,300 a month, including flights, lodging, food, everything. My money stretched furthest in Cambodia and least in Hong Kong, which was financially similar to New York City. For comparison: my overhead, including my mortgage, maintenance, electricity, and WiFi in New York today is about $2,500 a month.

In terms of cost of living comparisons, here's my breakdown

Healthcare was the biggest surprise, in the best way. I got into a motorcycle accident on the Pakse Loop in Laos, and seven stitches cost me around seven dollars, including painkillers and a week of antibiotics.

Cambodia was the best value. It's the most adventurous, outdoorsy country I visited, and I didn't want to explore alone, so I stayed in hostels for as little as $6 a night — partly a budget move, mostly a way to meet people. It's also where I met my first fellow Americans of the entire trip.

Hong Kong was the opposite — groceries and eating out gave me real sticker shock. I softened it with a genuine energy exchange: I moved in with a college friend and threw dinner parties several times a week, cooking meals for them in exchange for a place to stay. It was worth every dollar — I met some of my truest friends and future business partners there.

The layoff was honestly the best thing that ever happened to me

It gave me the confidence to build DrinkFolks, a better sense of my heritage, and a version of myself I'm proud of. I've learned to never say never, but right now, I'm exactly where I'm supposed to be.

My advice is to use your layoff as your launchpad. Things happen for you, not in spite of you. If you have even the slightest chance to live in that moment for yourself — for me, that was travel — take it as a gift and a blessing, not a crisis to survive.

Treat budgeting as freedom, not constraint. My money stretched so much further than I imagined. Clear parameters gave me the space to figure out who I am outside my job.