My inbox is full of friends and colleagues who want to discuss life after Big Tech. Not surprisingly, older workers seem to be disproportionately affected by the recent layoffs in Seattle as tech companies (Amazon, Meta, Expedia, etc.) spread layoffs driven by overemployment in the pandemic, the shift to AI and job-related housecleaning.
Most of the 50 items that have just been released on Amazon are in full frenzy mode. They were shocked by the broken promise. They are working hard to get into Big Tech. They have been well paid for 10, 20, or 30 years. And now they find themselves on the list and in a Zoom meeting with an HR manager who is doing mass layoffs. Kids in college or headed there on $60-100k a year. Health care costs run $2-3k per month for a family. Reach out to buy that Seattle or Bellevue home with a monthly payment of $5-6k. Aging parents need support. Your spouse asks how they can help.
Fear. The instinct is to move quickly, fill the calendar, make something happen. Repost. Call that recruiter again from six months ago. Network like crazy. Click on LinkedIn. Adrenaline is quick to understand right now.
My advice: Wait. He took a deep breath.
For 50+, this is not just another career change. This could be your last chapter. You’ve got another career opportunity and maybe 25 to 30 years of life left, if you’re lucky.
Time is a very precious resource. Why would you spend one of them doing something that doesn’t enlighten you?
People come out of big tech companies – Amazon, Microsoft, Google – with amazing skills and knowledge. They can do almost anything. And that becomes a problem. When you can do anything, how do you choose?
Find the horizon with four elements
Every business needs a strategy. Now you are “one business.” It’s important to do the hard work of figuring out where you want to go before you hit the road and start driving. There are many ways to determine your goals and priorities in life. I am a big fan of Career Coach Tim Butler from Harvard Business School and his latest book called “The Four Elements.”
The framework is simple but powerful:
Step 1: Find your move
Think three times in your career when you are fully engaged. Lost time. You felt like you were doing what you were meant to do. Write down what makes those moments special. Combine similar items into one sentence.
Step 2: Find your signature skills
What were you good at? Not what your job description said you should excel at – what really empowered you and created an impact? Think of three times when you were at your best. What patterns do you see?
Step 3: Define your ideal environment
Come up with five adjectives that describe when you feel at home at work. Then write the opposite. To me? Playing vs. Serious. Individualistic competitive group. Mission Driven vs. Bureaucratic. Those polarities tell you a lot.
Step 4: Map your horizons
Who do you need right now? Spouse/children/parents/siblings. What are your financial obligations? Housing/college/parents/kids. What is most important in this next phase of life? Money? Do you give back? Spirituality? Friendship? Traveling?
Step 5: Discuss AI
Take the data from Steps 1-4 and have an interview with your LLM of interest. Mine is Claude, but this works with ChatGPT, Gemini, or Copilot. I have also uploaded a bunch of personality tests and the result of work that I am proud of in my career (strategies, business plans, presentations, killer reports). My personal project in Claude now knows me, my strengths and my weaknesses better than anyone in the world (save my wife ☺).
When I did this exercise and checked my answers, a pattern emerged. I thrive in fast-growing, high-risk environments with strong teams, focused on customer value, with a lot of freedom to explore and execute. I need a job that feels important. And at this stage, I want to work on things I’m curious about, with people I love, for a strong social purpose.
Career Sprints: Check before you commit
After doing some soul searching, here is the next part that many people skip: use the tests.
I call them “career races.” Come up with a thesis – two or three references you might want to go to. Then find more affordable ways to exercise before you commit to another five years.
Looking to buy a home services business? Find someone who uses one and promise to work for free for three months. See if it really empowers you or if it seems like a good idea.
Thinking of working in retail? Same thing. Use your time off to do a full-time job either free or paid and deep enough to know if you would like to spend the next five years doing it.
I did this in 2015. I got tired of selling ads and software on the internet for money. I wanted to find my purpose. I thought maybe I wanted to work for a non-profit, so I spent three months at a large homeless shelter. He loved the work and the people. But work? Too slow and not enough for strategic execution. I felt like I was turning the crank and wasn’t happy enough with the daily grind. Then I tried venture capital for six months (my third time in VC). VC involves a lot of meetings, a lot of self-promotion, and a lot of social events. Personally, I really like building new businesses and working with a team to charge a mountain. I like to be on the field and not on the sidelines or in the owner’s box. So investing was not for me.
That check saved me from making costly and time-consuming mistakes. (Or at least making those mistakes as I have made many others).
When you’re 50+, kids are starting and maybe 5 to 15 years of good work left, you can’t afford to waste time on something that doesn’t give you energy. You may return to a product management role without thinking too hard. You can go make bombs or drones. There is a need for everything.
But is that how you want to write your last chapter?
If you’re down to 50+, here’s what I’d do:
1. Take at least 30 days (90 is better) to clear your brain
Don’t take meetings. Do not send a resume. Don’t start networking. Don’t pick up that recruiting call. Take a breath. Give yourself the grace to not think everything through quickly.
2. Do the Four Exercises
Get a book or use free tests online. Upload your answers to Claude or ChatGPT and have a discussion about it. AI won’t tell you what to do, but it will help you spot patterns you might miss.
3. Come up with a thesis
Based on what you’ve learned, what are 2 to 3 directions that really excite you? Not that logical. What makes you want to get up in the morning?
4. Run career sprints to test your thesis
Before you commit, find ways to try. Work for someone in that space for free. Shadow people. Get your hands dirty. See if it empowers you or disempowers you.
5. Set a strategy, then get a strategy
Once you know the direction, then You can update your resume and start communicating with the target.
When you’re 50+ and you quit, people consider it a disaster.
You’ve been given a gift — a chance to reset, to make a different choice, to prepare not just for a salary and title but for purpose and energy and the kind of life you want to live. Take time. Do the work. Figure out what chapter you want to write before you start writing it.
And if you found this helpful, consider reaching out and helping a friend who has just been laid off or is going through a difficult transition.
