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Getting Hired

Are You Ready To Be Lucky?

The new era of work requires us to constantly reinvent ourselves and our jobs in an uncertain world. Find out how to stay on top of your game.

We’re at an interesting crossroads in terms of careers. We still want them, but they don’t exist anymore. In the US, the typical job tenure is now 4 years, with most workers cycling through about 11 jobs in their lifetime.*

If the 20th-century career was a ladder that we climbed from one predictable rung to the next, the 21st-century career is more like a broad rock face that we are all free climbing. There’s no defined route, and we must use our own ingenuity, training, and strength to rise to the top. We must make our own luck.

The lightning-fast evolution of technology means that jobs can now become indispensable or outmoded in a matter of years, or even months. Who knew what a “Community Manager” was ten years ago? What about an “iPad App Designer”? Or what about “Chief Scientist” (at LinkedIn)?

A substantive portion of the working population now earns its livelihood doing a job that didn’t exist 10 or 20 years ago. And if your job itself hasn’t changed, chances are you’re using new and unanticipated technology and/or skills to perform that job. (E.g. You’re a designer who blogs, a comedian who uses Twitter, or a branding consultant turned e-tailer.)

A substantive portion of the working population now earns its livelihood doing a job that didn’t exist 10 or 20 years ago.

Ten years from now, we’ll probably all be doing some new type of work that we couldn’t even possibly imagine today. The thought is both exhilarating and frightening. How do we prepare for a future filled with uncertainty?

1. Explore, relentlessly. The tools you use today will not be the tools you use in the future.

You may have heard the term “life sport” before. It refers to sports – like golf, tennis, or swimming – that you can play from ages 7 to 70. The ever-brilliant Kevin Kelly recently expanded this concept to include technology as life sport, outlining a must-read list of “techno life skills” that we should all cultivate. As Kelly puts it: “If you are in school today the technologies you will use as an adult tomorrow have not been invented yet. Therefore, the life skill you need most is not the mastery of specific technologies, but mastery of the technium as a whole – how technology in general works.”

Whether it’s interviewing someone over Skype, developing an affable Twitter persona, learning how to publish an e-Book, or experimenting with a new task management app, we must become adept at testing out new technologies that can benefit us in our personal and professional lives. Sometimes, we will choose NOT to integrate a new technology into our lives, and that’s okay. It’s the experimentation, and the awareness that we gain through it, that’s key.

If you are in school today the technologies you will use as an adult tomorrow have not been invented yet.

2. Recognize like-minded friends and peers, and cultivate those alliances.

Technology will never change some things, and one of those is the power of relationships. As Ben Casnocha, co-author of The Startup of You recently told me, “Opportunities do not float like clouds in the sky. They’re attached to people. If you’re looking for an opportunity, you’re really looking for a person.”

Work, knowledge, and opportunities flow through people, which means that who we know – and how we know them – is our most important asset. But relationships don’t get built by exchanging business cards. They get built with energy, care, enthusiasm, and, most importantly, time – lots of time.

Ten years ago I worked at a publishing startup, and I still know at least 10 people from that job, who have gone on to become creative directors at a global design agencies, architects at cutting-edge firms, lead product developers at digital music labels, fashion entrepreneurs and editors, social media gurus, and the list goes on. You never know where people will end up.

Work, knowledge, and opportunities flow through people. Who we know – and how we know them – is our most important asset.

3. Help people whenever you can. Don’t expect anything in return.

We can all be pretty sure we’re going to need help at some point in the future. As leadership expert and ethnographer Simon Sinek articulated in a rousing 99U talk, “We’re not good at everything, we’re not good by ourselves.” Sinek goes on to describe how the ability to build relationships is the key to our survival as a race and to thriving as idea-makers. The number one way to build relationships, of course, is by helping each other.

But in an age of complex connections and contingencies, there isn’t always a simple 1-to-1 correlation between acts of generosity. (As in, “I’ll scratch your back, you scratch mine.”) And there shouldn’t be. Helping our peers, colleagues, and allies should be a regular habit and its own reward. We usually can’t foresee how, but the goodness always comes back around.

4. Keep learning – on the job, and off.

If you want to stay at the top of your career game, indulging your curiosity is your greatest asset. It could mean attending conferences or lectures relevant to your current occupation, or spending an hour every weekend on Code Academy, or finding an excuse to interview the people you admire most.With resources like Coursera, EdX, Khan Academy, Skillshare, General Assembly,, and more, there’s no excuse not to expand your knowledge. If you can create something tangible that you can show a potential employer in the process (e.g. a writing sample, a portfolio piece, a website, etc), even better.

If you want to stay at the top of your career game, indulging your curiosity is your greatest asset.

5. Be proactive about proposing new roles and tasks.

The days of “grooming” young employees for senior positions are over. No one is going to spend more time thinking about your career than you are. (And, honestly, why would you expect them to?) As NY Times op-ed columnist Thomas Friedman writes, employers “are all looking for the same kind of people – people who not only have the critical thinking skills to do the value-adding jobs that technology can’t, but also people who can invent, adapt and reinvent their jobs every day, in a market that changes faster than ever.”

You won’t be rewarded with exciting new opportunities by keeping your head down and following the rules. If you want a new challenge at work or more responsibility, it’s on you to pitch your boss or your client on what needs to be done, why it’s a good idea, why you’re the best person, and why everyone will benefit. Lead the way with your own creativity and initiative, and back it up with enthusiasm and a strong business case.

6. Always be asking “What’s next?”

If you’re not asking questions, you’re not going to find answers. And we often wait to ask those hard career questions right up until the very moment when we direly need answers. We wait until we get laid off to think about what’s next. Or we wait until we’re completely miserable and burnt out at our jobs before we ask, “what’s next?”.But if you’re going to switch jobs every four years or less, you should probably be asking yourself “what’s next?” all of the time. I’m not talking about asking “what’s next?” in a way that disengages you from your current job. I’m talking about asking in a way that helps you push yourself.

Asking in a way that helps you hone in on your passion. Asking in a way that helps you decide what new skills you want to develop. Asking in a way that helps you reach out to meet that new mentor. Asking in a way that helps you take on that big new project at work that kind of scares you.

Asking because if you don’t ask, you’ll never find out.

What’s Next For You?

How are you preparing for rapid-pace career changes? What questions are you asking? Share your tips in the comments.

More Posts by Jocelyn K. Glei

A writer and the founding editor of 99U, Jocelyn K. Glei is obsessed with how to make great creative work in the Age of Distraction. Her latest book is Unsubscribe: How to Kill Email Anxiety, Avoid Distraction, and Get Real Work Done. Her previous works include the 99U’s own bestselling book series: Manage Your Day-to-Day, Maximize Your Potential, and Make Your Mark. Follow her @jkglei.

Comments (54)
  • Kevin Kestler

    Great post, Jocelyn! Re: #4, at mojoLive we recently launched a beta product that allows professionals to track, share, and be rated on each and every step—big or small—towards personal and professional improvement; the end goal being overall career success, not just the next job. Anyone who’s interested can check it out here:

  • Sofia Garcês

    Great post thank you for sharing it with us! In this new world we absolutely have to keep learning new skills, and most of all realize that no one will care about our future more than we do!

  • Chris

    Fantastic article Jocelyn! Something that I’ve been examining myself that fits into this discussion is expectation, and in particular: not allowing expectation to get in the way of progress or dictate success. I’m going to borrow from Conan O’Brien’s Dartmouth commencement address because, well, it’s better than anything I’ve got to say: “It is our failure to become our perceived ideal that ultimately defines us and makes us unique. It’s not easy, but if you accept your misfortune and handle it right your peceived failure can become a catalyst for profound reinvention.”

  • Richard Batista

    Great Post! Articles like this keep me on my toes and help me inspire and motivate the team around me. If you have patience to learn through and other related websites then you have my respect 100%. Many people I know say I want to learn but are too busy complaining rather than going on their own and asking “Wants Next”! Thanks for the post!

  • James

    Oh my gosh! This is what I’ve been thinking and telling people for so long, but I love how you’ve made everything so concise. It’s so true that everything is moving fast, here’s an awesome video that goes more in depth about the future. It will blow your mind, especially with how soon it is. Here’s a trailer –

    Thanks so much for this beautiful article!


  • Jonathan Patterson

    Excellent. I know so many people that wait around but never act. It’s all about action. Even if you don’t make the “right” decision upfront, at least you’ll be on your way.

  • creativeinfluences

    This is a great motivational and inspiration article! It’s so true nowadays that you can’t remain stagnant with your current ideas. There is always something to learn!

  • 2gnōME

    Great article! In a job interview you never want to complain, be cynical or exude negativity, but you do want to be likeable because interviewers will recruit people that they like. The same holds true at social events and the logic is simple; people are subconsciously drawn to those who have a likable personality.
    This holds true for your social life as well. One of the most important keys to living a happy, healthy and fulfilling life is having the ability to build meaningful relationships. Many factors influence the connections you have with others, but being a likable person is a key element.

    For more see our blog:

  • David Shindler

    Excellent post, Jocelyn, that sums up the difference between getting a job (short-term, risky) and employability (lifelong, security). It’s like a sailor negotiating the next wave as opposed to navigating the boat whatever the sea conditions. The thrust of what you say is about attitude and mindset which are more enduring than skills (which can be learned or developed) or knowledge (which can be acquired) and neither will be the same in 4 years time. I’d sum it up as ‘act your way into a new way of thinking’.

  • jkglei

    That’s a great quote, Chris. Thanks! (Also, the recent Conan O’Brien doc is amazing. Did you see it?) That reminds me of a Toynbee quote I just discovered, which is sort of the inverse: “Nothing fails like success.”

  • jkglei

    So true. There is no new information without action.

  • jkglei

    Thanks Sofia!

  • Deanna Morono

    How is it that I’m 24 and have the mindset that job security is obtainable? I feel like I’ve done everything you’ve pointed out, but it’s still hard. And very scary.

  • jkglei

    Hey Deanna: I think we all carry around a residual hope for long-term security. It’s natural! And being called on to constantly plan and adapt IS scary. But, when thought of from another perspective, it’s pretty liberating, and it’s certainly not boring. ; )

  • Julia

    what an awesome article so simply and intelligently written. I love the points and suggestions re moving forward.This gets my 100% Luv it!

  • BC

    Inspiring post! It is all true, I have always been on these thoughts throughout my design career. Keeping one’s mind and enthusiasm, as well as “toolset” sharp is very important.

  • K K Goh

    Great post, but I disagree on (3) “Don’t expect anything in return”. Maybe it’s just semantics.

    While you should be helpful and “pay it forward”, there should always be an understanding between both parties that at some point in the future, you may be calling on that favor someone owes you or that they should proactively return that favor. It’s not a zero-sum game or 1-1 correlation like you said. But if you don’t make it publicly known what it is you need (i.e. marketing), no one will ever bother thinking about you when the opportunity comes and you’re doing yourself a great disservice.

  • Julia

    Hey Deanna,

    You’re not alone in that idea. I’m 31 and have found myself working in offices with people who have a 15 to 20 year service record with the company. The downside is that the 15 year people often get to keep their job, while junior workers like us have higher turn over. The plus side that I’ve found… someone who has been at the same job for 20 years has a horrible time adapting when they’re finally forced back into the job hunt. As much as I am jealous of those with long-term stability, I’m also thankful to stay out of a rut.


  • Deeae

    It’s also completely exhausting. After all the activity of adapting to the world’s inexhaustible demands, you realize you have been eaten up instead of sustained prospered; your actual life is bankrupt. Drop out of career madness and live. You absolutely don’t need what you’re being sold in your twenties and thirties. Sooner or later you realize you’re dying alongside the world (it can’t give what it doesn’t have) and will look for your life’s revival and sustenance elsewhere.

  • Svetlana

    Great article! A lot to ponder!

  • SuperP

    One of the best pieces I’ve read in a long time! Thanks a Million.

  • Azley Jones

    Great article and well written!


    Visual Artist
    Shubha A Hebbar is a visual artist from Bangalore.Bachelor’s degree in Fine Arts from the College of Fine Arts,Karnataka Chitrakala Parishath, Bangalore. For his M.V.A dissertation on Dot & Circle. obtained a Master of Fine Arts degree from M.V.A University, Bangalore University in( Print Making )
    My works are “Conceptual” so it presented a unique way of its (Abstraction of its own Figurative) Juxtaposed to form a transparent of select images net in sense of tradition but to show two heads of
    same coins.
    My thought process begins inspired by instantly images selected by “readymade computer images” on this serve as a material (New Media) to express my thought as parallel many research made to concert my concept which support as foreword this helps me the growing of my work constant recapping, rejoining, reinventing for new realization of rare experience to exists my world as you viewing.
    Passion to achive highest goal in designing feild,like to display my art works if their is a chance like to work in studio… pls let me now like to work in the designing field as visualiser, let me now if their are any…
    Shubha A Hebbar

  • Darshan


  • Heinz Rainer

    Excellent article well written indeed. Needs time to digest all points raised.

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