How to Future-proof Your Career

🚀 The world of work is changing so quickly - Issue #193

We get hung up on job titles, responsibilities, and the tasks we perform in our daily work. We get too focused on what we do. For example, I have friends who would define their profession as one of the following:

  • Designing websites

  • Repairing car engines

  • Developing mobile apps

  • Installing electrical panels

  • Selling real estate

  • Flying private jets

  • Coaching fitness clients

Unfortunately, the focus on what you do influences performance and success metrics too.

  • How fast can you design?

  • How cheaply can you repair this thing?

  • How many lines of code did you write?

  • Did you turn around the spec in less than a week?

  • Are you more affordable than this other professional?

Sam Altman, the president of Y Combinator, wrote a blog post about how to be successful. If you care about your career, I encourage you to check it out.

A section called “Be hard to compete with” resonated with me, since that is one of my critical messages for my career clients. In it, he says:

Most people understand that companies are more valuable if they are difficult to compete with. This is important, and obviously true. But this holds true for you as an individual as well. If what you do can be done by someone else, it eventually will be, and for less money.” — Sam Altman

When you let others measure your value in some arbitrarily-quantified way, then the goal becomes doing more, faster, and cheaper. Hence, the last decades spent offshoring work and the recent push to automate work.

In this rush to “do more,” the big-picture questions of “Should it even be done at all?” and “Is it the right thing to do?” are set aside (e.g., Should we spy on our users?). The value of wisdom and experience is often completely overlooked. Faster and cheaper rule the day.

Don’t play their game

Don’t get caught up in this focus on what you do. Your actual value is what you know, and that — unlike skills that someone might replicate — only increases over time.

Expertise matters, and this continues to develop over the course of your life and career. For example, a study of radiologists found that their “interpretations of screening mammograms improve during their first few years of practice and continue to improve throughout much of their careers.”

How can you leverage your singular life and work experiences, your knowledge and wisdom, and your unique perspective to set yourself apart from everyone else for the rest of your life?

It reminds me of the times that my home requires some serious electrical work. I do a lot of it myself, so I know enough to be dangerous. But, I am by no means an expert.

I ask multiple electricians for estimates. They come to the house, I tell them what I think needs to be done, and they write a proposal.

The master electricians with the most significant knowledge and experience are never the cheapest, of course. But, a more critical distinction always emerges; they rarely offer a partial solution to what I think the problem is.

They know what the underlying root problem is and what a lasting solution should be, not the quick and obvious one.

The electricians with less knowledge, experience, and wisdom simply give me a direct quote to precisely do what I ask, even if it doesn’t solve the root problem or will create more problems later.

Both can literally “do” the same work. But only the masters know what actually should be done. For example, one said:

“This wiring issue is actually a symptom of a more significant problem. I can replace the wiring here and install GFCI outlets. But, what scares me is that the main box didn’t trip for some reason. It should have, but it didn’t. Let me run more tests on it. Replace that and your whole house will be safer, not just one circuit.”

Now, you might be thinking, “Of course, he said that. He padded the repair work to make more money.

However, I did some more research over the next few days and found out that those types of breaker boxes were indeed a problem. As they aged, they stopped working, and they eventually caused huge problems and even fires.

So, he was right. But, the less experienced electricians only looked at the isolated issue and wanted to jump to fixing that and walking away quickly.

Fast and cheap. That’s good, right? 🙄

Where to focus on maximizing your value

You must find a way to level up your value and tap into what others cannot replicate. Create the leverage that makes you hard to compete with. You need to increasingly focus on what makes you unique to stand out and be in demand forever.

Five essential areas will help you future-proof your long-term career:

  1. Knowledge

  2. Experience

  3. Wisdom

  4. Relevance

  5. Communication


Your knowledge is the culmination of what you’ve learned in school, on the job, and in every other aspect of your life.

While you may have started on somewhat equal footing during school, your path diverged from others. You made one career decision vs. another and pursued this profession vs. that one.

I’m sure that your knowledge has continued to grow as you’ve pursued different interests. Some of the highest value is created at the intersection of different domains, which allows you to make connections and see patterns that others cannot.

One of the best investments that you can make is to dedicate yourself to lifelong learning. Continue to evolve your knowledge and make it a core component of your unique value.


No one has precisely the same life and work experiences that you have had. Everything you have experienced impacts who you are and how you think. You can bring your unique perspective to bear on any problem that needs to be solved.

One way to maximize your experience is to get out of your comfort zone and try new things. Step up into bigger roles and take on more responsibility.

Do things that scare you. Growth happens when you stretch yourself to do and become more.

Your unique experiences enable a diversity of thinking that no one else can truly replicate. They have not lived your life.

They have not walked an identical career path (my career path is kind of crazy). Embrace this, recognize how your experiences contribute to your unique value and leverage it to your advantage.


Wisdom is one of those words that eludes simple definition. It isn’t merely accumulated knowledge. It also isn’t synonymous with experience.

There are plenty of knowledgeable and experienced people who don’t have wisdom. Or, they certainly don’t seem to exhibit it.

Knowledge alone does not solve problems. Wisdom helps you understand how and when to apply your knowledge.

Experience certainly helps with recognizing patterns and knowing what actually needs to be done vs. what pure knowledge tells you supposedly should be done. But, leaning on experience without the benefit of wisdom often results in falling into a rut and trying to solve problems the only way you know how to solve them.

I don’t believe that wisdom only comes with age. Many older folks don’t have wisdom.

Wisdom does require some knowledge and experience. You can’t live in a vacuum and understand how the world works, of course.

Wisdom is more than that. It is a way of seeing the world differently, questioning convention, and understanding higher-level relationships, interactions, and consequences.

For example, knowledge and experience might give you a clear solution to a problem that will certainly fix it right now. It might even be the very best solution if you only consider it in isolation.

However, wisdom enables you to envision the ripple effects of potential solutions, now and forever. Wisdom may direct you to what seems to be a less-than-optimal immediate solution but ends up being one that is better for everyone in the long run.


For you to achieve timeless relevance, you must always remain — well — relevant. That sounds a little recursive, doesn’t it?

What I mean is that you always need to be observing, learning, and predicting where things are going. Remaining relevant requires that you stay ahead of changes that will impact who you are and the value you can provide.

For example, smart print designers noticed that technology was changing everything in their world. They learned how to adapt their core talent to the online world, shifting into web and mobile design.

Stubborn designers clung to the industry and refused to learn and adapt. Many of them have been laid off over the past few years and are scrambling to find some way to remain relevant.

Another way to remain timelessly relevant is to identify evergreen needs.

  • What is always true about the world, human beings, and their interactions?

  • What will people always need, no matter how much technology changes things?

  • What is your unique value that others will always want?

  • What are your core talents that will always be relevant and in-demand?


Here is where most people run into trouble, even though they have deep expertise developed over a long life of experiences:

  • They don’t know how to explain what they know.

  • They don’t know how to communicate and share their knowledge in a useful way with others.

This is the Curse of Knowledge. Once we know something, we find it hard to imagine what it was like not to know it. Our knowledge has “cursed” us. And it becomes difficult for us to share our knowledge with others, because we can’t readily re-create our listeners’ state of mind.” ― Chip Heath, Made to Stick: Why Some Ideas Survive and Others Die

To stay relevant, you must be able to communicate your knowledge, expertise, and wisdom to those who will benefit from it the most. You can do this in person, through your writing, or any other form of sharing that works best for you (e.g., podcasting, videos).

If your unique experiences and valuable knowledge stay locked up in your head, why should anyone care?

Not everyone is naturally gifted at teaching and communicating clearly, but you can learn these skills.

  • Simplify things by getting down to the essence of your ideas.

  • Make it specifically relevant and meaningful for your listeners and readers.

  • Use analogies that bridge the gap between your knowledge and theirs.

  • Connect your message with what they already know well.

Start planning now

We all become knowledge workers if we live and work long enough and accumulate considerable experience in a specific profession. Don’t sell yourself short. You are more than the tasks that you do.

Now, you might be thinking, “Hey, I’m young. I’m just getting started in my career. I have plenty of time to figure this out later.

However, outsourcing and automation don’t only impact the careers of “old people.” If what you do right now in your job can potentially be automated or performed more affordably by hiring someone else, your employer is thinking about it.

I watched it happen time and again in Silicon Valley. The company would lay off our local engineers, and then we’d hire firms outside the U.S. to provide the engineering resources we needed at a much more affordable price.

If you’re also thinking, “There’s no way my job could be automated,” think again. Advances in Artificial Intelligence (AI) will impact more jobs than you would ever imagine. For example:

I’m not trying to scare anyone. But, I’ve been in the working world for a long time, and I’ve coached numerous people through sticking points in their careers. I’ve seen this pattern play out over and over again, across multiple industries and professions.

You have to make yourself difficult to compete with, and you must always be repositioning your unique value to stay ahead of the changes in the industry.

Again, Sam Altman has some wisdom to share:

The best way to become difficult to compete with is to build up leverage. For example, you can do it with personal relationships, by building a strong personal brand, or by getting good at the intersection of multiple different fields. There are many other strategies, but you have to figure out some way to do it. Most people do whatever most people they hang out with do. This mimetic behavior is usually a mistake — if you’re doing the same thing everyone else is doing, you will not be hard to compete with.” — Sam Altman

Some people think of this as investing in their side hustle, and it can be.

  • You could start writing and sharing your wisdom now.

  • You could start doing some consulting work outside of your 9–5 job.

  • Or, you could simply start playing an advisory role and sharing your knowledge with those who would benefit from it.

But, I prefer to think of this as investing in your endgame. You’re probably not in your very last job right now. I’m guessing something will come next for you, again and again, for several years.

The world is going to keep changing. Technology will keep rewriting the rules. Jobs will come and go. Entire professions will disappear.

You can’t only focus on getting better at what you do since what you do may no longer be relevant 10, 15, or 20+ years from now.

For you to have lasting value, you have to change the rules of the game and be willing to stop chasing what everyone else is.

Focus on what you, and only you, can bring to the table; your unique knowledge, personal experiences, and hard-earned wisdom. Be able to communicate this and make it useful for others, and you’ll remain relevant forever.

New jobs and opportunities

  • As the Group Product Manager driving monetization strategy and execution for Trello, you will lead a team of passionate Product Managers and partner deeply with your peers in Engineering and Design to delight customers and grow revenue. You will be responsible for the performance of the business, setting direction, executing on an ambitious roadmap, and growing the world-class Product Management team under you! Learn more…

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  • Spoonflower is also looking for a Head of Diversity, Equity, Inclusion & Sustainability (DEI&S) who will champion a diverse workplace and inclusive environment and will bring thought leadership, insights, and perspectives to their unique business. This person will provide strategic and operational leadership on diversity, equity and inclusion policies, programs, and practices across the global organization. Learn more…

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