• Aliena Cai left eBay to launch Fast Track UX, an online UX design course.
• Cai initially relied on her YouTube channel for marketing, but later expanded her strategy.
• She learned to value her services, outsource help, and manage her time effectively.

This as-told-to essay is based on a conversation with Aliena Cai, 26, an entrepreneur based in Seattle. It's been edited for length and clarity. Business Insider has verified Cai's business and revenue.

In my two years as a senior product designer at eBay, I worked on high-impact projects with incredibly smart people. During that time, I used my creativity to post on my YouTube channel about UX design as a side hustle.

When I felt I was making a solid revenue from YouTube ads and sponsorships, I quit my six-figure tech job at eBay and went all in on my long-term goal. I wanted to create my education program called Fast Track UX — an online course.

In the two years since then, I've built a strong clientele and grown my income back to six figures, but I made several mistakes along the way. If I could go back, I'd tell myself to do four things differently to save time, money, and energy — including a warning that the grass isn't going to be greener on the other side of corporate.

I should've put more time and resources into promoting my product sooner

I credit my initial program sales to YouTube subscribers who already trusted my UX advice and enjoyed my teaching style. Organic marketing on my YouTube channel helped me build a strong clientele of over 1,000 students, but I think there was likely a much larger audience out there that didn't know my course could be helpful.

I had only done ⅓ of what's required to sell a product. I had identified an issue, but I still needed to get people to know this problem existed and make them willing to pay to have it solved.

So, I started making more YouTube videos addressing this gap. My approach was to use broad, curiosity-driven titles like "If I started UX in 2025, I'd do this," in which I included specifics about real skills and workplace expectations that aren't taught in typical UX certificates or bootcamps.

I found that this helped reach a larger audience. I've also started making more Instagram reels because Instagram naturally pushes content to a wider audience.

I shouldn't have undervalued my services

This was my first time ever having to be a salesperson for myself, and it felt very phony. I felt a huge friction when it came to marketing my product and asking for money because it felt like such a big responsibility. Unfortunately, I let that fear hold me back from promoting my product as fully as possible. I even underpromised its value in fear of disappointing customers.

For example, I explicitly said that I wouldn't provide any feedback to customers, but I ended up giving personal feedback to hundreds of people. It's only in the last few months that I actually listed feedback as one of the offerings. It's still a work in progress, but I'm learning to express the value I see in my product.

I should've outsourced help sooner and not been cheap about it

For the longest time, I felt like my worth was tied to my achievement, so I didn't outsource help because I didn't want to allow someone in who could jeopardize that feeling of worth. But that mindset only drained me of time and energy until I had nothing to give.

I finally hired a video editor last year, but I made the mistake of prioritizing cheap labor over quality.

The first editor I hired was inexpensive, but I had to give so many rounds of feedback that it took more time than if I had just edited it myself. My current editor is more expensive, but his work is clean, and I can relax knowing that the work will get done. I should've outsourced much earlier.

I should've been more realistic about becoming an entrepreneur

Having complete freedom over my own schedule requires a lot more skill and discipline than I once thought. There were days in the beginning when I would feel stuck scrolling on Instagram reels for hours, only to feel more miserable than if I had gone to a corporate meeting.

Managing my time is still a challenge, but I've made improvements by designing my own tool. It visualizes tasks by urgency and importance, and includes a "roll the die" feature to make choosing your next task both strategic and a little fun.

Here's what I did right as an entrepreneur

When a lot of people want to start a side project, they get stuck on the first step, sometimes forever, because they're waiting to feel like they have the perfect product for the perfect market.

I let the market find me. I released so many different types of YouTube videos, and when a UX design video went viral, I stuck with it.

I shared different product ideas with my audience to gauge their interest, and sent out questionnaires to learn their perspectives. I let the idea take shape with an open mind.

I'm trying to maintain that mentality as I focus on enjoying my entrepreneurial journey. Every day, I remind myself how lucky I am to be enjoying this journey of designing, even if it's just for another Instagram reel or YouTube video, because it means so much more than the outcome.

Do you have an entrepreneurship story to share? Contact this editor, Manseen Logan, at [email protected].

• Annie Lu left Atlassian after working for over two years and taking a 12-week medical leave.
• Lu's departure followed structural changes and a shift in project assignments.
• She said departing was a hard decision that has led her to a more fulfilling life.

This as-told-to essay is based on a conversation with Annie Lu, a 32-year-old former product marketing manager at Atlassian based in Bellevue, Washington. It's been edited for length and clarity.

When I got hired at Atlassian as a product marketing manager in late 2022, it was a dream come true.

For the first few months, I was working on projects that leveraged my interests and skill set. I also loved the culture, the hybrid work schedule, and my colleagues. It was exactly what I was looking for.

After a while, I noticed Atlassian following the growing trend in Big Tech of increasing structural reorganizations, layoffs, and cost cuts. As priorities shifted to more macro-level changes, I slowly stopped being assigned to projects that felt impactful, creative, and aligned with my skillset.

I tried to push through, but I hit a wall in early 2025 when I felt my body shutting down. I took a 12-week medical leave to recover, but it only made things clearer. When I returned, I quit, and it was one of the hardest decisions I've made.

How I spent my 12-week medical leave to recover from burnout

I spent the first month of leave restoring my physical health and regulating my nervous system by eating well, sleeping consistently, moving my body, and even making time to play. I slowly reintroduced some of my hobbies like journaling and reading, and finally began reflecting on what I wanted next for my career and life.

Falling into burnout made me realize life is short, and no paycheck or title is worth more than my well-being. I realized I had a lot of limiting beliefs, including that I needed to follow a conventional corporate path to success rather than pursuing my passions.

When I returned from medical leave, I decided to leave Atlassian. It was time to take a leap, explore, and pursue my passion for writing.

Quitting Big Tech was a step toward the life I truly wanted

I walked away from a stable, six-figure paycheck with stock options, great health and wellness benefits, and a flexible hybrid schedule. And more importantly, I stepped away from the career I had worked years to achieve.

But after structural changes, I no longer felt connected to my work or its purpose, which made it difficult to find motivation and work through stress. I knew quitting was a step toward the life and work I truly wanted.

After quitting my Big Tech job, I feel so much more fulfilled

When I quit, I felt like I was stepping away from something good to get something even better.

It's been just over a month since I quit, and I already feel so much more fulfilled. I'm writing about my burnout experience to reach others who feel stuck in corporate but want to pursue their passions or live a more fulfilling life.

I'm taking this new journey one step at a time

My next step is building a portfolio career in the creative space. I'm funding this transition period using savings and relying on the support of my husband, who is still working.

There's a chance future me will want to go back to corporate given the right opportunity, but right now I'm enjoying focusing on solopreneurship. I don't know what the future is going to look like, but I'm enjoying the process and not focusing on results.

Did you leave Big Tech and want to share your story? Email the editor, Manseen Logan, at [email protected].

• Jaylyn Jones landed over 12 interviews without tailoring her résumé for ATS scanners.
• Jones, a recruiter, emphasizes showcasing job competence over keyword stuffing in résumés.
• She shared which advice she found least helpful when she submitted her résumé through the scanner.

This as-told-to essay is based on a conversation with Jaylyn Jones, a 32-year-old recruiter based in Pittsburgh. It's been edited for length and clarity.

One of the biggest job-seeking myths I've heard is that aggressive Applicant Tracking System (ATS) scanners will filter out applicants whose applications are formatted a specific way. That's just not the case.

I've been a recruiter for three years, and about a year ago, I started hunting for a new role. When I was applying for new recruiting jobs in 2024, I took my personal experience using ATS systems into account and proved that I didn't need to tailor my résumé for ATS scanners to land a position.

Here's how I formatted my résumé to stand out among the rest.

I've used ATS scanners to recruit people for jobs

My first recruiting job was at JP Morgan from 2021 to 2024, in which I used Greenhouse, a popular ATS system, to help streamline the recruiting process.

Greenhouse rejected or flagged candidates based on straightforward questions like "Are you over the age of 18?" and "Are you authorized to work in the US?" However, no applicants were filtered out by keywords or formatting. If 1,000 people applied, I saw 1,000 applications.

I could manually search for keywords if I wanted to look for someone with specific experience, but that didn't get rid of applications that lacked that keyword.

On my résumé, I focused less on keywords and more on showing my ability to do the job

I went bullet-by-bullet on every job description and made sure there was something on my résumé that showed my competence in that area.

When reviewing my résumé, I'd simply ask myself, "Would a reasonable person look at what I have on my résumé and say, "Yes, they can do this job?" My strategy worked; I got interviewed by over 12 companies, and I got hired to recruit at a tech company in less than three months.

In my current role, I receive a lot of résumés that are filled with a page worth of keyword fodder before getting to actual experience. Once it reaches the experience section, that part is just as filled with buzzwords. When I see a résumé like this, it's not a red flag. I see it as somebody who has not been given the information and tools to be successful.

Jobscan gave my résumé a failing score

Recently, I plugged the résumé that landed me my most recent job into Jobscan, an online résumé scanner that ranks how strong a résumé is, just to see what the platform would say.

The biggest critique I received was that I was missing keywords. For example, the scanner said something like "the job description says the word "recruiting" 13 times, but your résumé only says it twice." Then it prompted me to add the keyword more times.

It was also very particular about language, such as bumping my score down for saying I was a "campus recruiter" at JP Morgan instead of a "university recruiter." It gave my résumé a 16% score.

As a recruiter, I honestly didn't see any tips from the résumé scanner that would be useful for a job seeker. If anything, it can be harmful to an applicant's success if they're more caught up in using the word "evaluate" than actually citing their experience evaluating.

My biggest tip is to focus on providing evidence over keywords

So many job seekers are having such a difficult time in this market, and they're doing everything they can possibly think of to be more successful, but if you're going to use AI, don't be sloppy.

A common ChatGPT prompt that job seekers might use is "Tailor my résumé to this job." AI often responds to this by shoehorning keywords from the job description into haphazard bullet points. Using keywords isn't helpful without proper context.

I prefer uploading the job description and using the prompt "analyze my résumé for any gaps in skills or qualifications based on this job description, and make suggestions about what to change." This might cue you to add any missing skills that the job post is looking for.

The right prompt allows job seekers to own their experience, not just blindly trust ChatGPT. This helped me during my job search.

Editor's note — A representative from Jobscan sent the following comment to BI : "A Jobscan Match Rate isn't a grade on your career; it's a risk assessment against a frustrating system. A low score doesn't mean you're unqualified; it means you're at high risk of being invisible to the automated or manual filters that 88% of employers admit will vet out good candidates. Based on third-party research and our own surveys and conversations with job seekers and recruiters, Jaylyn's job search experience is certainly an exception to the rule."

If you are professional with helpful résumé tips you'd like to share, please email the editor, Manseen Logan, at [email protected].

• Patrick Lyons was laid off from Microsoft twice and worked there for a total of six years.
• Despite layoffs, Lyons maintained financial stability through side businesses and severance.
• Lyons advises pursuing monetizable passions to mitigate the impact of potential layoffs.

This as-told-to essay is based on a conversation with Patrick Lyons, a 29-year-old ex-Microsoft employee, based in Austin. It's been edited for length and clarity.

After five years at Microsoft, the last three of which I was a technical product manager for Microsoft Teams, I felt fulfilled and completely secure in my job.

I learned new things every day, pushed boundaries, and collaborated with brilliant minds. I saw how people needed me and called upon me at work for my expertise, and it brought me a real sense of purpose.

I had also been running three side businesses outside of work for several years, namely an online fitness coaching company. This allowed me to pursue my fitness passion while having bidirectional income streams. I had no plans for anything to change.

Then, in October 2024, I woke up to an early call from my VP letting me know that my role had been permanently eliminated due to business restructuring. I was shocked, but my next thought was, "How can I get rehired?"

During my unemployment, I enjoyed my hobbies

The next day, I started looking at Microsoft's internal job portal, which I'd only have access to for two more weeks. I didn't have any success in that period, so I started applying to jobs at other companies while keeping an eye on Microsoft openings.

Despite the stress about my sudden layoff, I was financially stable because of my businesses and a generous severance.

I spent the next few months applying to jobs and pouring my time into hobbies like improv comedy, fitness, and movies. It was one of the best times of my life. I started having such a good time away from work that a big part of me started questioning if I shouldn't go back to corporate at all and just fully commit to my fitness businesses.

I kept finding myself coming back to how much I missed Microsoft

I missed the ritual of logging into Microsoft Teams, doing my job, and collaborating with the same great people. I loved feeling as though I was really contributing to something larger than myself.

Microsoft's work culture is unbeatable. The idea of a growth mindset was tangible in our daily work, and our expectation was not to be a "know-it-all" but a "learn-it-all." I was surrounded by brilliant minds who wanted to help me become just as brilliant, not put me down for making mistakes or questioning the status quo.

A few months into unemployment, a former mentor of mine at Microsoft forwarded my résumé to a hiring manager, and I got rehired at Microsoft as a program manager for Azure, a cloud computing platform.

I got rehired and laid off in two months

When I returned to Microsoft, I treated my job the same as before, but I doubled down on my communication to make sure I was always on the same page with my team and superiors. It might sound counterintuitive, but I felt even more job security this second time around, because Microsoft had invested a massive amount of money into Azure.

Two months later, I woke up to a nearly identical message inviting me to a meeting where I would be laid off again. It was so jarring. I've already started applying to jobs again, but to be honest, I would still go back to Microsoft if I had the chance.

Even though Microsoft can be political at times, as there is a clear hierarchical structure in which you often have to cater to leaders' preferences, I feel as though I've learned how to navigate it. I can't always just "do" things; I need to consistently present and seek out buy-ins from various leaders.

My advice for people going through layoffs

I've stayed so level-headed while navigating two layoffs because I have diverse income streams.

My businesses allow me to completely support myself and remain in a comfortable financial position. However, I'm still choosing to seek out full-time employment because of health insurance and my desire for multiple streams of income.

I don't think it's possible to be lay-off proof, but you can limit the ability of a layoff to cause harm to your life. If you have something outside of work that you're passionate about that you can realistically monetize, do it.

If you have a unique layoff experience you'd like to share, please email the editor, Manseen Logan, at [email protected].