5 Skills That Will Control Your Destiny in a Future of Change

Jake Wilder
9 min readNov 4, 2018


When We Can Adapt to Change, We Can Succeed Through Change

“It is not the strongest or most intelligent who will survive but those who can best manage change,” said Charles Darwin, defining not only the key to evolution, but also the key to relevancy in today’s world.

The world we live in is ever-changing. And unlikely to slow down anytime soon.

Today’s technical expert can be full of obsolete knowledge in less than a year. Skills and abilities that once guaranteed success are now no longer enough. The previous playbook of memorized process loses its value if the process keeps changing.

While change used to be gradual, it’s becoming much more rapid. What was previously incremental is quickly becoming unpredictable.

I don’t know what the world will look like in ten years. And the more that people claim to have this foresight, the less likely they actually do. But it’s a relatively safe bet that it’ll be different. And we’ll be faced with any number of changes that none of us can predict.

Without the ability to adapt with that change, we give up our agency in a changing world. We forfeit the opportunity for an active life and relegate ourselves to one of passive drifting.

A new world brings new industry. New industry brings new jobs. And new jobs bring new sought-after skillsets.

So while few of us can predict the specific technical capabilities that will be critical in the future, we can prepare ourselves to adapt into them by developing a core set of behaviors. And not simply survive, as Darwin intended, but thrive in this changing world.

Embrace Iteration

“Few ideas work on the first try. Iteration is key to innovation,” said Udacity co-founder Sebastian Thrun. Yet how many people are prepared to handle iteration?

While we’re growing up, most schoolwork includes working on a project, taking a test, and then handing it in for a grade. After which, we move on to the next thing.

Doing something over is equated with the idea that it was done poorly. We’re taught that the first attempt should always be perfect.

Yet in industry — and particularly in a changing industry — iteration is everything. Nothing is perfect on the first attempt. As Debbie Millman put it,

“Expect anything worthwhile to take a long time.”

Without iteration, we don’t recognize the importance of feedback. We lack the direct consequence from seeking out feedback and constructively applying it. And we limit our development to our own biased perspectives.

Without iteration, we gain little experience in looking at a struggling product and finding ways to improve it. And we miss out on developing the practice of looking at the same problem in different ways.

The solution is to ship. Get your product out there and look for real feedback on how it’s performing. Incorporate, improve, and repeat.

And realize that nothing great is ever great on the first try. Or as Maria Popova once described,

“Progress is incremental for us, both as individual creative beings and together as a society and civilization. The flower doesn’t go from bud to blossom in one spritely burst. It’s just that culturally, we are not interested in the tedium of the blossoming. And yet that’s where all the real magic is in the making of one’s character and destiny.”

Ask (Great) Questions

“It is not the answer that enlightens, but the question.” — Eugene Ionesco

As many of us grew up, we quickly learned that answers — not questions — were rewarded. Answers move us forward. Questions delay. So it shouldn’t be surprising that while a lot of people specialize in giving great answers, few excel in asking great questions.

And yet it’s the questions we ask that separate the innovative few from the conformist many. The ability to ask great questions is a check against our tendency to seek instant gratification and to plod along the same tired, familiar paths.

Everyone is trying to develop new answers to the same, familiar questions. It’s a market full of competition and a push for incremental gains.

But new questions tend to open new markets. They help us look at those same problems from a new perspective — and see something that the rest of the competition doesn’t. As Krista Tippett is fond of saying,

“Answers mirror the questions they rise, or fall, to meet.”

When Edwin Land was vacationing with his family, his daughter asked him why they needed to wait to see the pictures he had just taken. While it was common knowledge that film needed to be developed in a dark room, her question spurred him to challenge this convention. He would go on to develop the Polaroid Instant camera.

Bette Nesmith Graham, a bank secretary (and heavy typist) by day and artist by night, questioned why she couldn’t paint over her typing mistakes as she does with her artwork. She filled a bottle with a mixture of paint and water and developed Liquid Paper — a company she later sold for nearly $50 million.

When everyone else is trying to answer the same questions, the person who can change the question provides a new direction. As the great management consultant Peter Drucker once said, “My greatest strength as a consultant is to be ignorant and ask a few questions.”

Encourage Diverse Opinions

“People who change their minds because they learned something are the winners, whereas those who stubbornly refuse to learn are the losers.” — Ray Dalio, Principles

It’s become a social embarrassment to not have an opinion on a topic. So we encourage people to quickly develop one based on a superficial understanding of the facts and a couple quick sound bites from the echo chamber of their choice.

And once developed, we associate these opinions and thoughts with our very identity. We consider challenges to our positions as the equivalent of an attack on our very person. A process which doesn’t exactly encourage people to share new ideas and different perspectives with us.

In many cases, we’ve reached the point where people are unwilling to even hear arguments that conflict with their current views. As if their opinions are so fragile that they risk jeopardizing everything by merely exposing them to a new perspective.

But it’s important to remember that neither side has a monopoly on reason and intellect. And without an open mind to new opinions, we actively prevent ourselves from growing. As George Bernard Shaw put it,

“Progress is impossible without change, and those who cannot change their minds cannot change anything.”

We should all remember that it’s much more rewarding to understand than to be right. And true understanding only comes from exposing ourselves to diverse perspectives. Above all, we should remember the fifth tenet in Carl Sagan’s Baloney Detection Kit,

“Try not to get overly attached to a hypothesis just because it’s yours. It’s only a way station in the pursuit of knowledge. Ask yourself why you like the idea. Compare it fairly with the alternatives. See if you can find reasons for rejecting it. If you don’t, others will.”


“If you are going through hell, keep going.” — Winston Churchill

I was interviewing a candidate the other day when I asked him to tell me about a time where he struggled to overcome an obstacle. He told me that he’s never really struggled with anything.

Which left me with two main thoughts: (1) he’s either lying, delusional, or too afraid to go beyond his comfort zone. Possibly all three. And (2) there’s no way to trust that when he eventually hits those obstacles, he’ll be able to handle them.

We fetishize the person who keeps striving in the face of all obstacles. We idolize the entrepreneur who never gives up and keeps pushing despite waves of rejection and failure. A dangerous and misleading model.

Because for every Sarah Blakely who succeeds in this model, there are a hundred people who spend their entire lives struggling against the same rejection and the same obstacles.

Perseverance is not persistence. It’s not simply doing the same thing over and over again. A Sisyphean strategy of pushing the same rock up the same hill in the same way is not an admirable trait. In many cases, it’s just stubborn idiocy.

Perseverance is much more than persistence. It’s dealing with adversity. It’s recognizing that we need challenges and the struggles to overcome those challenges. And then trying a different method to make it happen. As Seth Godin told Tim Ferriss,

“If you think about how hard it is to push a business uphill, particularly when you’re just getting started, one answer is to say: ‘Why don’t you just start a different business, a business you can push downhill.’”

We often say that people need to overcome their fear of failure. I don’t believe this is true — people actually aren’t afraid of failure. We see people failing every day — often running headfirst with practices almost designed to ensure this result.

People aren’t afraid of failure — they’re afraid of failing differently. That’s why people stay in the same dead-end jobs and repeatedly try the same ineffective methods that haven’t yielded results. They’re choosing guaranteed failure via established methods over even the chance of failing differently.

Perseverance is much more than persistence. Yes, it’s standing by our commitments. And it’s not giving up in the face of adversity. But mainly it’s about being brave enough to fail differently.

As Walter Eliot described it, “Perseverance is not a long race; it is many short races one after the other.”


“It is easy to see the faults of others, but difficult to see one’s own faults. One show the faults of others like chaff winnowed in the wind, but one conceals one’s own faults as a cunning gambler conceals his dice.” — The Buddha

Ask people if they consider themselves to be self-aware- and nearly everyone will make this claim. Yet research shows that only about 10–15% of us actually demonstrate effective self-awareness. As psychologist Tasha Eurich described it, “that means that 80% of us are lying to ourselves about whether we’re lying to ourselves.”

We’re surrounded by journaling and meditation advice, all focused on helping us to better connect with our own minds. But too often we fail to turn this introspection into worthwhile learning. Eurich blames this on our obsession with asking “Why?”

Asking ourselves “why” questions pushes us into unproductive negative thoughts. It causes us to ruminate over our fears and insecurities instead of making a rational assessment of our strengths and weaknesses.

Instead of focusing on “why” try asking yourself “what” questions. Not “Why did this happen” but “What do I need to do differently next time.” Not “Why do I struggle with these responsibilities,” but “What are the situations where I typically struggle and what do they have in common?”

Instead of guessing at motives and beating ourselves up after the fact, asking what we could have done to handle something differently makes it action focused. It helps us recognize ways to handle things more productively in the future. And it keeps us focused on solutions instead of on the unproductive patterns of the past. In the words of Lau Tzu,

“At the center of your being you have the answer; you know who you are and you know what you want.”

Embrace a Future of Change. Embrace an Active Life.

“We can change. People say we can’t, but we do when the stakes or the pain is high enough. And when we do, life can change. It offers more of itself when we agree to give up our busyness.” — Anne Lamott, Almost Everything: Notes on Hope

We all have the capacity to adapt with a changing world. But first we need to be willing to let go of the current version of ourselves — those fixed mindset identities that are laden with weights of comfort and self-righteousness.

The choice between an active life and one of passive drifting lies in our commitment to adapt and change as the world changes around us. It lies in our decision to equip ourselves with the skills we need to set our own path despite a changing world around us.

Everyone has this choice — we don’t need to know the future to prepare for it. Choose an active life. One that lets you dictate your own path. And you’ll never be satisfied with passive drifting again.

Thanks, as always, for reading. If you enjoyed this or have any suggestions, please let me know your thoughts. I’d love to hear from you. And if you found this helpful, I’d appreciate if you could clap it up👏 and help me share with more people. Cheers!



Jake Wilder

I don’t know where I’m going. But at least I know how to get there.