This as-told-to essay is based on a conversation with Kymm Dracup, a 56-year-old based in Toronto. It's been edited for length and clarity.

My daughter says, "Don't worry, Mom, you'll get a job. I've seen your résumé, you're great." I don't think my daughter realizes the effect that my age, 56, has on my confidence and finding work.

I was unemployed for 22 months before landing a temporary consulting job a few months ago. There's no guarantee for a transition to full-time work, and I'm really scared about my future.

I've been rejected countless times, and I recently got evicted from my home. Unfortunately, I think my confidence took a hit, and my desperation for a job is coming through in my interviews.

I never learned why I lost my last job

I was the head of the management team for a group travel company for three years. In 2024, my job was terminated.

I asked for a reason, but I was never given one. In Ontario, you don't legally need to give a reason, so that was it.

It was very tough on my confidence to get let go. I still don't know the reason, but my best guess is that they were bringing in younger people with fresh eyes and innovations to replace me.

It's difficult to prove that age is hindering my job search

After losing my job, I started applying wherever I could, mostly for travel jobs, and later, any sales job. I received rejection after rejection.

I've been stood up for interviews, received automated rejections, and even had recruiters find excuses to end calls after seeing my face on camera.

Have you ever felt your age was a factor in a job rejection? Scroll down to the comments and share your experience.

It feels obvious to me that age is a factor in why I can't find a job, but the tricky thing is that there's no real way to prove that any of these rejections are due to my age. It hurts, and I don't feel as though recruiters see my value.

Applying to jobs felt different 5 years ago

When I was on the job market five years ago, I don't think AI was being used to sort through résumés.

Additionally, I've never interviewed online before now, and quite frankly, it's a bit intimidating. Therefore, I may not come across as confident, as there is an insecurity factor lending to the video.

I know how to sell myself in person, but I find it difficult, especially at my age, to do so over Zoom. You can be vibrant, brilliant, and all these things, but it's tricky because my generation is so geared to meeting people face to face. That is where we shine.

There are also only so few jobs available. I applied for an entry-level receptionist role for a yoga studio, and they stood me up for my interview. So many people are looking for jobs, and I think older people might not be the first to get hired.

I think my desperation for a job is making it harder to get one

As a single woman in my 50s, I don't have a partner to financially support me during this time. I feel desperate to find a job, and though I don't want it to come across that way to hiring managers, I think they can feel it.

When I get another rejection, the self-doubt that I'm worthless, too old, and that nobody will hire me comes back up, and the desperation intensifies. It's a vicious cycle. I try to tell myself, "Kymm, pull up your socks. Let's go. Go on to the next interview," but in the back of my mind, the doubt is still there.

Sometimes I'm joining an interview after not leaving the house or speaking to people for days. When I get an interview, I can't just snap my fingers and get out of that dark place.

I got evicted from my home and moved in with my daughter

My daughter has offered to let me stay in her home since I now have an income. I'm helping her pay bills while I figure it out.

I think it's very difficult for her to have a parent who is all of a sudden in need. I raised her as a single mom. I was strong, and now I just crumpled to the ground.

I've been in a really dark place, and I know that's not easy for her. What is helping me through this time is turning to God. I have to believe in something.

I wish I had been more prepared for unemployment in my 50s

Most people coming out of university these days are learning AI and are up to date with modern technology. When you bring in someone my age, it's different because the technology we had in school was pretty archaic.

I had no idea how difficult it would be to navigate the job market. I wish I were more prepared for all of the "no"s because it can be really hard on your self-esteem.

I wish that life experience were viewed as a more valuable asset in the workplace. It's been very hard to get out of that dark mindset when I keep receiving rejections. My advice is to find a way to believe in something better for yourself.

Sometimes belief is all you have, so you've got to hold onto it.

Are you navigating a career change in your 50s? Contact this reporter at tmartinelli@businessinsider.com to share your story.

• Jea Park walked away from her tech career at 32 to pursue a job in the trades.
• She said she no longer enjoyed working in tech, as AI has become more embedded in daily workflows.
• Her biggest challenge is finding an apprenticeship, but she is excited about the change.

This as-told-to essay is based on a conversation with Jae Park, a 32-year-old based in Las Vegas. It's been edited for length and clarity.

About a decade ago, I took a furniture-building class on a whim, and I loved it so much.

I considered going into carpentry at the time, but after leaving college with six-figure debt, I gave up on the idea of having my work tied to something I was actually passionate about. Instead, I wanted to pursue a path that could let me make more money.

Over the past year, as my tech job pushed me to incorporate AI into every aspect of my workflow, I wanted out. It felt like I was on a giant cruise ship with the company trying to make a U-turn as quickly as possible, and everyone was falling off the ship. So, I left in March.

After I left my tech job, I walked into the trade union office with the plan of becoming a carpentry apprentice at 32, but finding an apprenticeship has proven to be difficult. Still, I'm so overjoyed with my decision.

I worked with a union rep to learn about apprenticeships

I always aspired to work in tech for its stability, pay, and benefits. Once I got in as a sales enablement ops strategist, however, I felt very disconnected from my work output and realized there wasn't much I enjoyed about the industry.

One time, I was listening to a podcast where the hosts briefly talked about a push for women entering the trades, and I thought, "You know what? Let's give this a shot."

On my first visit to the trade union office, the union rep walked me through the compensation packages, benefits, and four-year carpentry apprenticeship programs. I'm in a lucky position where I don't have kids or own a home, so I started to feel really great about this opportunity.

I had to provide documents to the trade union and complete a 10-hour construction course on the OSHA website that cost $60.

Finding an apprenticeship has been the trickiest part

To get sponsored for an apprenticeship, I was instructed by the rep to visit active construction sites listed by the trade union and speak with the foremen.

It made me really nervous, but I went to seven construction sites in one week. It was confusing, at times, because there was no real direction. Sometimes, there would be an address of an entire casino, but no information about where the construction site was. It took a lot of problem-solving, but the nice thing is that the union has a lot of people to talk to, and they can give tips and tricks.

A lot of times, the foreman was really busy, so I had to use my people skills to find the right time to jump in and give them a quick pitch.

I'd take about 30 seconds to introduce myself as a new apprentice and see if they had any opportunities. I thought I had an opportunity, but it turned out their program hours weren't compatible with the union's, so I'm back to showing up at job sites.

It's been almost a month, and I'm still not sponsored

I'm interested in millwork, but it seems to be in a slow period right now. To make sure I get an apprenticeship, I'm taking down the foremen's phone numbers and setting reminders for myself to call them later this year when more jobs pop up.

I can technically look for work in specific scopes outside of millwork, and it would count toward my apprenticeship. However, I'm not pinched for cash immediately, and I'd really prefer to land a millwork job to start.

I'm glad I'm getting into the trades in my 30s

When I finally decided to join carpentry, I was bummed out, thinking, I wish I had joined when I was younger. In hindsight, I'm glad I'm bringing all of my life experiences with me.

The trades are male-dominated, and it's hard work. I think I had to spend over 10 years in my professional career to understand my boundaries, know when to push back, and stand up for myself. If I had joined the trades when I was 18, I don't think I would've made it.

I also now know that the corporate route is 100% not for me. If I had gone into the trades first, part of me would have always wondered if I should've tried corporate.

I'm confident in my decision to leave tech

I'm so overjoyed about my decision to pursue carpentry. Even though I know unions aren't perfect, I'm looking forward to being a part of a system of employment that's worker-first.

I went to my first union meeting, which was the biggest culture shock. It's so cool to have dedicated time for people from different organizations to talk, share experiences, and offer support. I almost cried during that meeting. I was like, "I've never felt so supported."

I've only just begun this journey, so we'll see how it goes, but I'm so excited.

Do you have a story to share about joining the trades? If so, please reach out to the reporter at tmartinelli@businessinsider.com.

• Tehmina Watson is an immigration lawyer who advises startup founders and businesses.
• Watson says there has been panic and confusion about the most recent immigration policy memo.
• She advises tech workers to get in contact with their lawyers now to address their visas.

This as-told-to essay is based on a conversation with Tahmina Watson, a business immigration lawyer in Seattle. It's been edited for length and clarity.

When I saw the administration's new immigration policy memo last Friday, stating that I-485 forms will only be approved in "extraordinary circumstances," I felt like the sky was falling.

The I-485 is the form used to apply for a green card (legal permanent residence) from inside the US. The last several days have been filled with fear, stress, and confusion, from people who don't know what this means for their status, and if they'll have to leave the country.

I'm the founding attorney of Watson Immigration Law. We specialize in business and family immigration. One of our areas of expertise is working with startup founders and businesses that are expanding into the United States, and many of my clients are tech workers.

It's hard to wrap my head around the enormity of this decision because the I-485 is used in almost every category of immigration to allow people to adjust their status from visa to green card.

This change will have a ripple effect on everyone. Laid-off tech workers are in a particularly difficult spot. My advice is to get in contact with your lawyer now and gather documentation.

Green cards will only be granted to those in 'extraordinary circumstances'

People can apply to adjust status to permanent residence from inside the US by filing Form I-485 with USCIS.

While the memo initially stated that I-485 forms will only be approved in extraordinary circumstances, a USCIS spokesperson clarified that those who bring economic benefits to the United States will be viewed favorably in their adjudication. However, there's no real policy guidance yet.

Typically, if somebody has arrived in the United States legally, they can adjust their status to that of a green card holder without leaving. The memo is essentially saying the intent of the law is that people get their applications filed outside the US, and that they're returning to the intent of the law.

The last 72 hours have been full of fear, stress, and confusion

Since Friday, my email has been blowing up with people asking, "What does it mean? What do we do?" The immigration lawyer community has been scrambling to figure out what this means as well, so Friday was very much about a lot of analyzing, discussing what we're going to do, and setting up calls with our clients.

So much is still uncertain. As the week unfolds, we might see more clarification from the administration. We may actually see litigation on the subject where the policy could actually be completely or partially enjoined. I sincerely hope that the courts will enjoin this policy.

I think a lot of my guidance to people will be dependent on what we hear from the administration in the coming days.

If you're on a work visa, start gathering documents that prove your economic benefits to the US

A lot of my clients work in tech, and the question that's been coming up since the memo release is what happens to people with work visas, such as H-1B.

On page five of the memo, it states that "maintaining lawful status in a dual intent non-immigrant category is not sufficient on its own to warrant a favorable exercise of discretion." To me, that means my clients need to file even more documentation to prove the economic benefit that they bring to the United States.

I'd advise people to get in contact with their lawyers and act urgently. For work visa holders, it will be important to sit down with their lawyers and figure out what kind of positive economic documents they can submit with their adjustment applications to prove the economic benefits they provide.

This policy will have a ripple effect on people and businesses

If a policy like this continues to go forward, families could be separated for years, likely because the consulates will not be able to shoulder the burden of the volume that will be required to adjudicate.

This means the people currently waiting will wait longer, and those who are being put into the system will exacerbate the system.

It will also mean that the businesses that invest in their workers are going to suffer because their workers will have to wait outside the country.

Laid-off tech workers are at risk

There are categories of people who never intended to be out of status, like folks who've been laid off from their tech jobs.

Laid-off workers have a 60-day grace period to find another employer to sponsor their visa or change their visa status to an interim visa, such as a tourist visa. However, it appears that the administration could be taking the perspective that those who apply for an interim visa have not maintained status.

If Big Tech companies are laying people off and not hiring, where are these people going to be able to get jobs to maintain their status? The ripple effects of this change are going to be felt everywhere.

Do you have a similar story to share? If so, please reach out to the reporter at tmartinelli@businessinsider.com.

• Courtney Clapper started applying for jobs in 2025 after graduating from Cornell Tech.
• She tried video cover letters, portfolios, and more to stand out, but had no luck.
• A hack on Reddit helped her get in contact with hiring managers and land her strategy lead job.

This as-told-to essay is based on a conversation with Courtney Clapper, a 32-year-old strategy lead for a major retailer in New York. It's been edited for length and clarity.

I started my job hunt in the fall of 2025, a few months after graduating with my MBA from Cornell Tech. I was applying for a mix of roles, such as product manager or digital strategist, and I knew the competition would be fierce in this tough job market.

From portfolios to video cover letters, I tried all sorts of creative methods to stand out and show off my personality, but they didn't work. A simple, free AI tool that locates hiring managers' emails landed me multiple interviews — and a job.

Video cover letters were a great start for me

My first thought process when entering the job market was to imagine myself as a recruiter, getting slammed with thousands of résumés filled with data and numbers.

I figured it would be in my best interest to give them a sense of what makes me stand out: my personality. So, I recorded myself reading my AI-written cover letters, throwing in a joke or two, and attached the video via a private YouTube link.

The video tells the recruiters I can speak and present well, and it gives them a sense of who I am. This approach helped me land an interview at Microsoft. They specifically called out the video, saying it made them feel like they already knew me, which I thought was pretty good feedback.

I still wanted to try several different creative ideas.

Next, I decided to make something more visual — a portfolio

My portfolio was in the form of a timeline. It included pictures of all professional endeavors I thought could help me land a job, from products I've built and my time at Cornell to pictures of me pitching. My goal was to showcase my skill set and personality while also creating something more visually interesting.

I'd also heard of people getting jobs by putting together a slideshow on how they'd improve the company, so I gave it a shot, and it didn't really get me anywhere. Neither of these strategies was worth the time commitment they required.

Referrals also got me nowhere. I have a solid network, and that wasn't making a difference. Interestingly, I applied for a bunch of roles at Microsoft, and the only one I got an interview for was the one I didn't have a referral for.

I came across a job-finding hack on Reddit

I was reading comments on Reddit from people complaining about their job-hunting struggles, and I saw a few people saying they found success by reaching out to hiring managers directly.

Some people said they cold-called, which made me think, "Okay, that's a little bit too far," but the emphasis was just to reach out. The idea of emailing them seemed low-risk, so I decided to give it a shot.

I started by researching on LinkedIn, trying to guess who the hiring manager or recruiter might be. Sometimes it was listed, but it wasn't the best method. Then I came across a Reddit comment about Apollo AI, a free tool that can locate hiring manager emails. I found it to be pretty accurate, so I started reaching out with my résumé and cover letter. It was a game changer.

The CEO of Sweetgreen responded to my email

My messages showed initiative and, honestly, probably just made things easier for the hiring manager. I reached out to three people directly and got interviewed for two jobs.

I even emailed the CEO of Sweetgreen directly, and he responded by putting me in touch with the hiring manager to schedule an interview.

One of my email reachouts turned into my current job, a strategy lead role for a major retailer. This strategy made things more efficient because I already had a direct line of contact, so it was easy to follow up if there was a delay.

I didn't get any negative feedback about it and would do it again

I was wondering if anyone might be weirded out about me finding their emails, but no one said anything. They could find it creepy, but they could also find it resourceful.

If I were back in the job market, I'd start with the email strategy. The exercise of thinking through creative approaches like portfolios and video cover letters was fun and got me thinking about how to present my personality most effectively, but ultimately, getting in direct contact was the best way to be competitive.

Do you have a story to share about a unique job-finding hack? If so, please reach out to the reporter at tmartinelli@businessinsider.com.

• Camillia Nwokedi left her tech career to become a content creator in 2025.
• She started with $6,000 in savings and experimented with posting for 60 days before leaving tech.
• Nwokedi said the journey is lonely, but it's the best decision she has ever made.

This as-told-to essay is based on a conversation with Camillia Nwokedi, a 28-year-old content creator based in Pittsburgh. It's been edited for length and clarity.

When the crypto startup I was working for was sold in July 2025, I saw it as the perfect opportunity to go all in on myself as a content creator. I had about $6,000 in savings and less than 40,000 followers on TikTok, but I believed I was worth the investment.

In less than a year, I've gained brand deals, consulting and coaching clients, and I'm launching my second cohort soon. I'm taking the lessons I learned from the startup to build myself from the ground up.

It's been a difficult emotional journey, but investing in myself is the best decision I've ever made.

I worked at Accenture before getting into crypto

I worked at Accenture from late 2019 to 2021. Bitcoin was popping off at the time, and I started getting the itch to get into crypto, so I started listening to podcasts and building connections in that space.

In 2022, I connected with the CEO of a bitcoin rewards platform, and we hit it off right away. He offered me a job as a special ops agent, and I took it.

The team was really amazing, and I had a lot of senior responsibility, which I loved. At the same time, I was building a social media presence on TikTok and Instagram, where I posted about optimization, self-belief, competence, and more.

In mid-2025, the company was preparing to be sold, and I saw it as an opportunity to give myself a shot. I had been posting consistently, and it really gave me confidence to start looking at myself as an entity and not just a cog in the system.

I had helped scale and sell for other people, but now it was time to give myself that opportunity.

I did a 60-day trial run before going all in on content creation

In the 60 days prior to leaving the startup, I did a series on TikTok called SIM 60, where I posted a video each day pretending to act like a video game Sim. It was all an attempt to get me out of my head, put myself out there, and make content creation more fun. What it did was unblock me as a creative and force me to stop taking myself so seriously.

My audience significantly grew in that period, which gave me confidence that I'd be able to make life as a content creator work.

There are two necessary components for creating a startup: finances and self-belief. And sometimes, if you don't have the financial component, your self-belief can make up for that gap. Getting my self-belief up helped me feel as though I could go all in.

I started with $6,000 in savings and created a research and development budget

A lot of the initial planning was trying to get my working capital in place so that I could make this leap. I had about $6,000 in liquid savings and a retirement account with about $30,000 in it, which I didn't want to touch.

It wasn't a lot to go off of, but because I had been putting myself out there on social media consistently and even had a few user-generated content (UGC) and brand deals coming in, I had a lot of self-belief.

I even gave myself a research and development budget, so I had a little money set aside if I wanted to invest in coaching or consulting to help me with my branding. Thankfully, I haven't touched my retirement account.

I set quarterly goals and have days dedicated to things like CEO and CFO responsibilities

I looked at all the roles that I would have to maintain as a one-person business and decided to split my week into days dedicated to each role.

I have CEO day, COO day, CMO day, and more. It makes it so that every part of me can show up at the table, but I'm not necessarily asking myself to do it all at once.

Tuesdays are typically consulting and operations days for me. This is when I get things in order and execute things for my clients. As much as I've left the 9-to-5, I try to work within that realm for the structure. It helps me manage my time well without overwhelm.

I also give myself quarterly goals or KPIs, which has been comforting. It adds familiarity and structure to a space that is entirely new territory for me.

It's been an emotional and lonely journey

The most challenging and the most worthwhile part of switching from tech to content creation has been the emotional journey.

One morning, I cried because I was so stressed. There's a lot of discomfort that comes along with pursuing my goals. It can feel lonely to be building something entirely on my own.

I have to gentle-parent myself and my nervous system to keep going, and to keep believing that it's going to pay off.

It's hard to communicate to people how many internal conversations I have with myself on a daily basis to reframe old narratives and rewire limiting self-beliefs.

At the end of every week, I can't believe I made it

If you're considering leaving your job or making a big leap, don't ignore that feeling or settle.

I think people often stay as close to their dreams as possible without actually going after them directly.

As someone with not much savings who is still pursuing her dream, and it's working out, I could not recommend it more. It's the best decision I've ever made, and I hope others can have the experience of pursuing what they want as directly as possible.

Do you have a story about leaving tech and pursuing a different career you want to share? Email the editor, Manseen Logan, at mlogan@businessinsider.com.