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.