Advice for the next generation

What I wish I knew about tech jobs when I was 25

Cartoon by Rex May

Yeah, the title makes me feel old, especially for a mid-40s guy. But I want to help you shape your technology career. So this article is a collection of lessons, refined over the years, that I repeat to 20–35 year olds in technology. I say tech careers because we are blessed to work in technology. We can work across many industries, labor is defined as mental (not physical) work, and we live in a golden era where impact is still in its infancy. And since it’s new and distinct from our parents’ professions, our careers require a new playbook and special care.

This is a long article, so here is the summary. When you begin your career, don’t try and optimize for short term wins. Your career is twice as long as you think it will be, given life expectancy gains and the diminishing value of retirement. Tech jobs last 3–5 years, so you’ll have a dozen or more jobs. You will also accumulate your net worth at a different time than you think.

When you hit age 40, you will be in your prime. Ensure you spend the years before 40 working in a learning environment, modeling as much as you can around you, building a powerful network and avoiding under or over-investing. Think of your career in its totality, not just the next few years. It’s up to you to invest in it wisely to maximize your earnings, impact and joy.

Let’s begin with three common misconceptions.

You won’t want to retire

Bold statement and obviously won’t apply to every one of you. But I suspect most of you won’t want to retire when the time comes. I realized retirement is going out of style reading a great Quora posting (which I can’t find! help me if you have the link). It answered the question, what do we take for granted today that essentially makes no sense. Answer: retirement.

Photo courtesy of Jeff Sheldon

Two to three centuries ago, working meant using our bodies. Physical work. No electricity. Jobs required constant labor so society was far more active. Our bodies worked hard and eventually broke down. Work also wasn’t joyful, so you looked forward to retiring and spending time the way you wanted. So when you hit your sixties, you stopped working. You rested, turned it over to the next generation and headed into the sunset.

In technology, we don’t use our body. Pressing a button on a computer doesn’t count. “Sitting is the new smoking” according to my doctor, and tech professionals are all addicts. We sit in a climate controlled room and type on a machine. We take breaks by moving into another room, sitting down and talking with a bunch of people. Then we stand up, get our free coffee, and head back to our desk. We don’t even plug in cables anymore, it’s all docks and wireless. The ultimate in convenience, yet essentially no physical activity.

And tech work is joyful for many people, as it is for me. We get to create things that don’t exist. This joy comes from social interaction, learning from others, and, most importantly, giving. Giving to the world and giving to your company and co-workers. Being busy while being relevant. Tech jobs may be sedentary, but most of us lucky enough to pursue them are happier in their jobs than any other previous generation.

But our elders (Baby Boomers) had a similar definition of joy yet still retired, following their parents and grandparent’s example. And when they did, for many of them, they found sadness. They stopped connecting with others. They became less needed, far less busy, and weren’t able to learn and give. They were physically capable with decades of life remaining, plenty of gas in the tank but no hill to climb.

My generation is watching this play out. Many of my friends are seeing their parents struggle with retirement and are deeply saddened and concerned. When it’s our turn, we will invent ways to keep busy, connected, relevant and avoid the same fate. Essentially replicate the joy from our tech career but shift our roles and focus and never fully retire. Ultimately working a lot longer and perhaps never stopping. And setting a new example for the next generation.

It all changes when you hit age 40

When I started, I looked for a job to “maximize impact and earnings” as fast as possible. Who doesn’t? Our heroes were Steve Jobs and Bill Gates, both known for their success and brilliance at an early age. Then came Larry Page and Sergey Brin, Mark Zuckerberg, Evan Spiegel, and countless other young, successful entrepreneurs.

So it’s commonplace to tell me you want the same — optimize impact and earnings right out of the gate. But in hundreds of past coaching sessions, I’ve learned an important lesson. Optimizing for early success is a foolish goal and is quite damaging.

A few years back I read this great article on career planning, and it was so profound, I still refer to it monthly. It asks readers to guess how much of their total net worth they will own by age 40. My guess was about 30–40%. The actual answer is an astonishing 10%. Meaning if your maximum net worth is $1.oM when you are age 65, you would only have earned $100K by your 40th birthday.

Test this with your friends over 40. It’s very true in my case, my personal wealth only grew when I crossed 40 years of age. Same story with nearly all of my friends. Note this applies to impact as well as net worth, i.e. 90% of your impact on the world and to others will come after the age of 40. While we aim for early success, it’s clear that Mark and Evan and Larry are extreme exceptions, not the rules.

I think this trend is even more pronounced in technology jobs. Here is why. You probably started your career in your early 20s after college. You had tons of energy and ambition, yet didn’t know how to navigate the workforce. You’re an expert sponge, not optimized to take action. But you compensate for inexperience with hard work, energy and a desire to learn.

15 years goes by. You’ve worked for multiple companies. Your nervous excitement is now a mature, balanced, and thoughtful perspective. You’ve learned from many leaders and perhaps have become one yourself. Yet you still have a full tank of gas. You are far from tired, keeping your foot on the accelerator. This perfect balance of experience and energy is at it’s highest peak between age 40–50. These end up being your power years of earnings and impact. And it’s the most important ones for you to optimize.

You won’t have a few jobs, you’ll have over a dozen

Photo courtesy of Leon Ephraïm

After reviewing 1000+ resumes in the past decade, people generally stay at tech jobs for 3–5 years. Technology companies change so rapidly, it’s rare to survive and thrive for 10 years. Markets change, companies transform, and culture evolves. So it’s normal to rotate to the next thing pretty regularly.

If you don’t retire and live past 100, you could work for 75 years, twice as many years as your parents did. If you average 5 years each stint, that is 15 companies. Some shorter, some longer, maybe you take a few breaks. So let’s say 10–20, just to be broad. It’s not 50, but equally unlikely it’s 5.

Optimize for your 40s, not your 20s & 30s

Going back to the original question. How do we career plan in our 20s? Answer: your 20s and 30s are all about investing in yourself, preparing for your 40s. When you are 40, will you have done everything possible to optimize your impact, your earnings, and your future joy? Will you look back and wish you did things differently?

I come across this language when I read about millennials. I resist the stereotype, since I’ve met many, across all ages, who seek immediate gratification and think short term. This is the wrong path. A recent video interview from Simon Sinek on Millennials does a superb job of describing where this thinking comes from and the dangerous consequences.

My fear is that you will seek instant gratification and fail to maximize your total lifetime success. Let’s compare two fictional journeys.

Photo by Caleb Ekeroth

Darwin hits the ground running as he enters the workforce. He’s driven, thoughtful, and makes an impact. But after two years, he’s disappointed he isn’t doing better. He believes he’s more talented than the senior people around him. He wants to manage, but the rules prevent him from doing so. So he jumps ship and starts a company, following his dreams. Three years go by, and his startup struggles. Markets change, startups are hard, and despite his best efforts, he sells the company and ends up in a large tech brand.

Though he’s been a CEO, he has few years of work experience. He’s leveled as a senior product manager or engineer, and after a year or two, realizes he’s not passionate about working for someone else. Big companies move slowly, he’s ready to take another crack at the industry, so he leaves to join a startup. The startup isn’t his, but he’s more convinced in the idea and the team. Yet the startup fails to hit it out of the park. Given he’s not a founder, he doesn’t see much return as the company merges with another competitor and he isn’t offered a meaningful role.

Darwin’s been out of school for 10 years now. He realizes he’s been bouncing around, but he’s not discouraged. He’s ready for a stable job. He looks for a tech job at a growth or scaled company, but has trouble getting the right role. Many of his classmates from college are in senior leadership positions at this point. But he can’t interview for senior roles, since he hasn’t managed, built something sustainable, and worked successfully at scale. So he ends up taking a role in a tier-2 company but is focused on sticking it out. So he does, as he enters his 40s.

Photo by Tyler Mcrobert

Darla is different. Darla joins her first job with similar ideals. Hard working, intelligent, yet focused and patient. She too realizes after a couple of years that she’s not having desired impact. She’s better than some of her superiors who are paid more. But she’s learning a ton and on track to gain more responsibility, which will really accelerate her learning.

So she sticks it out and has a strong reputation within four years. She’s launched a few products, some that worked, others that didn’t. She stays in touch with her former peers and managers. One of her former managers, who left to do a startup, offers her a team lead position. She jumps at the chance, knowing that the she won’t have to build trust with her boss. The company initially does well, but within two years, the market suddenly shifts and they are forced to cutback. She manages to stay afloat during this time, loyal to her team and ignoring the offers to jump to greener pastures.

Ultimately the company survives and gets acquired by a tech brand. She’s worked at scale successfully and has managed a team, so the acquiring company gives her a management role. Several colleagues from her past are here as well, and by her 10 year college reunion, she’s known as a rising star.

Darla is tired of working on the same product line, so considers other opportunities. Instead of jumping ship, she finds another role at the same company moving into their core business. Three years later, she makes Director. She now is learning strategy for a market leading product, and hot startups are calling her to join their leadership team.

On her 40th birthday, she gets a VP offer from a well funded hypergrowth company. And she weighs it against starting her own company, something she has always wanted to do. Her tech lead from her last company is loose and has an idea she is passionate about. And though she’s never founded, seed investors and friends have checks waiting to be cashed. She has a tough decision between two great choices and knows there isn’t a bad decision.

For Darwin and Darla, the work they do in their next 10 years, age 40–50, will clearly define their career. Darla invested while Darwin reacted. Darla used a far longer lens on her decisions, trading off short term pain for long term gain. In the following section, I’ll suggest how you should invest in those initial years to maximize your potential.

The office is another classroom

You spent the first 20 years of your life learning in classrooms. School is well structured with courses, levels, exams, and teachers. If you did well, you figured out how to study, take tests, and pay attention in class.

The job setting is another place to learn, but unlike school, requires a completely new set of tools to harness your education. It’s not a structured learning environment. There aren’t formal tests, classes or intense study sessions. You have to learn on your own, create your own lessons and courses, and seek out the teachers.

Photo by Cathryn Lavery

Choose a job surrounded by people better than you. In the beginning, be a small fish in a big pond instead of a big fish in a small pond. It’s hard to learn if you don’t have people to model. The alternative is to learn through trial and error. Throwing yourself into a situation is powerful and memorable, but very slow. Supplement learning by doing with watching and questioning others.

Note this doesn’t necessarily mean work for a scaled company. I learned a ton working for startups and starting my own company in my 20s. I quickly supplemented the few coworkers I had with friends from other startups, investors and advisors, and college classmates.

Second, ensure you are working on hard problems. Problems that aren’t easy to solve require you to grow and learn. They don’t have to be impossible, just hard enough to make your uncomfortable. If you are surrounded by coaches, you’ll avoid getting stuck. Receive just enough guidance to make lots of mistakes, ask lots of questions, and eventually overcome adversity.

Third, it’s your responsibility to gather feedback on your performance. You can’t learn if you can’t measure your progress. Despite formal performance reviews, the process won’t entirely identify your strengths and development areas. So don’t take the risk. Ask everyone and anyone how your last meeting went, how good your last code checkin went, if you are improving on your weaknesses. Do this monthly or perhaps even weekly. Don’t just ask your manager. Ask your peers, the admins, the folks in other departments, the execs. Anyone and everyone. And don’t forget to listen to positive feedback. All too often, high performers ignore compliments and miss this equally important signal.

People around you likely have a point of view on you. But it’s awkward to present it formally or interrupt your day. They’ll welcome the opportunity to share it, especially when you are eager to get better. And you’ll start honing in on patterns, update your development areas, and evolve.

Build models to accelerate your learning

Now you are off learning from others, working hard on your project, and getting feedback. Slowly but surely making progress. What if you could increase your speed of learning by 100x with a simple trick? Sorry to channel Ron Popeil, but this is no snake oil, it’s turbocharged education!

Image from Model Space

When I was a kid, I loved building models. Replicas of real life, it allowed my imagination to run wild with how the actual thing worked. I turned that passion from modeling physical things to modeling situations.

Imagine you are working as an analyst on a team but want to be a product manager. You’d love to define a feature and write a specification. This isn’t going to happen naturally, given your role. Don’t be a victim and wait around. Instead, take a crack at it. Take a few hours and actually write a draft. Build out the key points. You will have lots of holes since it’s new to you. But you’ll develop several points of view. When you’re done, grab the actual spec by the feature owner. Read through it and compare it to your own.

Where you find alignment, note how your instincts were right. Be proud and build confidence. Where you are misaligned, take notice and learn. Seek the facts you didn’t have and improve your judgment. Or stick to your guns and see if you invented a better solution. Review the spec feedback that others give, talk with the spec author and see how the feature unfolds in the market. All of this will help you build a model on how to create a feature. And give your practice on writing a specification and being a product manager.

“Sure, if I had the time to do everyone’s project, of course I would learn!” In essence, that is what I suggest, but with minimal detail. Develop a point of view for all events going on around you. You don’t have to commit it to paper, model things in your head. What should the next iPhone do? Where does Twitter go from here? How should your company attract more diverse candidates? How can your manager improve accountability? Develop a point of view then see how it plays out. Get better and faster in predicting what could happen vs. what actually happens. Each time, fine tune and bring the learning back into your own project and situation.

This is what I do. I carry dozens to hundreds of threads running in parallel all day long, some lasting years. A point of view on how something might end up. As each event matures, I compare it to my guesswork and tighten up my model. Do that for 20 years — you’ll have an unfair advantage like no other. You’ll see the full game board, not just the narrow section your job presents to you. You’ll develop near clairvoyance in sensing how things unfold. All without changing roles or companies or doing much more than deep thinking.

It’s as much who you know as what you know

Luck will play a big part in your career. I’ve met many talented people that never got that break. Not surprisingly, many others whose success isn’t based on mad skills. That doesn’t mean leave things to fate. It means find a way to create luck, and the more people you know, the more chances you get.

Photo by Anna Vander Stel

I’ll write a whole story on networking one day, but here are a few tips. Play the long game. If you seek people to advance your career, you’ll build relationships with others doing the same. Those are transactional relationships that rarely stand the test of time. Might as well connect on LinkedIn and call it a day.

Instead, identify people you genuinely find interesting. Build a long term friendship and relationship with them. Work hard to help when possible. You’ll have plenty of chances, since your colleagues will switch jobs a dozen times. Start with that mentor / co-worker who has shorthand with you, interesting candidates you interviewed, investors who passed on your company, managers who left for greener pastures, or friends of friends who totally understood your challenges.

Be creative in generating this list. Also pay attention to how you feel when you meet someone new, investing when you enjoy a conversation. On this topic, I love the book Give and Take by Adam Gross. He introduces the vocabulary of giver, matcher, and taker and suggests givers come out ahead in the long run. I find givers have an unnatural advantage in networking, since they don’t call it “networking” but “helping”. And it’s natural to maintain a relationship over time since it’s fun and impactful.

Know when to hold ’em, when to fold ‘em

When I was six, I knew every word from the Kenny Rogers song, The Gambler. I remember sitting in the backseat with my brother, singing at the top of my lungs. Safe to say my parents knew every word too, much to their chagrin.

Chorus: “You’ve got to know when to hold ’em. Know when to fold ’em. Know when to walk away. And know when to run.

Much of this article is devoted to extolling the virtues of investing. Avoid the temptation of greener pastures, focus on learning, deal with the punches your job will throw at you. Yet this is not a recommendation to stay unconditionally with your employer. In fact, it might require the opposite.

In Darla’s story, she strategically looked for a new role. She left when her next role was a step above her previous position. She didn’t leave as a reaction to her current work, but in anticipation to the power of her next opportunity. Running to something, not away from something. I’m astounded many don’t have a vision on what they want out of their current role. Don’t join a company, hope it’s enjoyable and valuable, and put your fate in your manager and the trajectory of the company.

Instead, join a company with a 24 month plan. Two years is long enough to know if you are in the right environment, growing, and hitting your learning goals. After two years, do you hold or fold and walk away? Actively decide on extending another two to three years. At the five year mark, the bar is higher to stay: you must be growing and learning at a powerful rate. We know leaving and starting over can be wasteful, but inertia can be equally dangerous. You must re-evaluate every few years and make an active decision to hold vs. fold.

Leaving will guarantee another name on your resume, diverse and new experiences, perhaps a new market, new co-workers, and instant learning. Five successful years at two employers is more valuable than ten successful years at a single employer. So stay for extended time only if you continue to grow at a healthy rate. Note it’s common to return in your 40s or 50s to a former employer. This allows you to leave, learn how another company solves the same problem, then return with a powerful blend of experiences in a senior, more impactful role.

I’ll end this section by noting that first and second generation immigrants disproportionately suffer from inertia. They often overstay instead of optimizing their career. I believe it’s unwavering loyalty that comes from coming to the country with little means. They cherish those who helped them grow roots and don’t want to be disloyal. I have to admit I am still working on reasons here. But it happens so frequently, it’s one of the most common gotchas I look for.

If you find yourself “stuck”, find others who have faced similar crossroads and came “unstuck”. And if you are an immigrant, your loyalty might be clouding your ability to invest in your career.


Thanks for making it to the end. I debated dividing this into separate stories but by pulling it together into a single piece, I can make this important point. In technology, managing your career is crucial yet navigating decisions can feel overwhelming.

Don’t focus on crafting a detailed long term career plan. Instead, focus on the investments you make and how you make decisions. Reactive, impulsive decisions, short term thinking, and placing your future in someone else’s hands will defeat you. Learn to trust and collaborate. Find a challenging yet safe learning environment. Run your career like a marathon, not a sprint. Become an expert at modeling and feedback. And ensure you consistently check in with yourself.

It’s an honor to help so many with their careers. I hope by writing these lessons down, you’ll benefit from this same wisdom and guide yourself to a joyful, impactful and challenging career.