Choose a career path that makes you scared of failure

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It is clear from a wide range of polls that the majority of both men and women under 40 are willing to give up power and money to get flexible and interesting work. The problem is that this is not so simple. Taking a low-paying, unimpressive job is not going to give you flexibility. In fact it will probably put you on track to be serving fast-food on a schedule that is so inflexible you have to negotiate with six people to cover your shifts during vacation.

The best way to get flexible, interesting work is to be great at something, and let everyone know your focus, according to research by Ezra Zuckerman, professor of economics at the Massachusetts Institute of Technology. This doesn’t mean being great at climbing the corporate ladder or great at working tons of hours to make partner at a law firm that will dump you. This means getting great at something because, according to Mihaly Csikszentmihalyi, professor of psychology at Claremont University and author of the book Flow, we feel best when we are doing work at a high level of competence.

On top of that, though, employers give flexible deals to people who are in high demand. It’s fortunate that the best way to be in high demand is to do the work you’re great at. Theoretically everyone will be very happy with their flexible, interesting work life.

So, how do you get to that point where you’re great at something?

It’s hard. It’s all about risk, honesty, and, frankly, shattered dreams. Your parents tell you that you can be anything, but you know what? You can’t. If you’re tall you can’t be an Olympic gymnast, and if you’re short you can’t be a runway model. If you’re great with numbers you probably can’t be a talk show host – the skills of a mathematician and a crowd pleaser seldom overlap.

So one of the most important things you can do is come to terms with what you are uniquely suited to do , and what you’re not–and to understand which is which.

Once you admit that some things will suit you better than others, you have to start trying things. Daniel Gilbert, professor of psychology at Harvard, wrote a whole book – Stumbling on Happiness – about how terrible we are at predicting what we’ll like, and nowhere is this more salient a point than in the job world. So start trying things.

Most of what makes people great at something is not raw talent but how hard they work at it, according to research by Steven Levitt, economist at University of Chicago and author of the book Freakonomics. So choose to do something you are excited enough about to work very hard at it, and keep testing things until something grabs you.

Paul Hatziiliades went through this process of self-discovery by starting as an accountant at a kitchen remodeling store. The sales guy left, with no notice, and Hatziiliades found himself greeting customers. And making sales. And liking it.

Then he kept learning about other aspects of the business until he was essentially designing kitchens, which he turned out to have great talent for. He’d have never known this about himself if he had been rigid in what sorts of roles he was willing to take on.

Even when you find that thing, though, at some point you will get stuck. You will see that you are probably great at something, but still not be sure of it. Maybe it’s a startup that you think you can make a go of; maybe it’s a freelance career that is almost sustainable; maybe it’s a big project that could change your career but is very scary.

All these things approach what Seth Godin calls the Dip. In his new book, The Dip, Godin explains that the things that are really worth doing in life – the things that will get you the passion and competence necessary for flow – require getting through a dip. And it’s at the dip where you decide if you can actually get to greatness.

Hatziiliades saw his Dip when the store owners decided to sell. Hatziiliades bought it and turned it into a high-end kitchen design company, called Moda Cucina, that leveraged both his talent for putting together kitchens that customers loved, and his talent for sourcing the right products and materials from all over the world. He had no idea if this business model would work, and he put all his cash into the business. This was the Dip for him. Today, he is on the other side of the Dip, doing what he’s great at, and being recognized for owning that niche he risked everything to get: high-end kitchen design.

Not everyone has Hatziiliades’ experience, though. Sometimes you’ll find you can’t do it – you can’t get past the Dip. Maybe you are trying something that is not the best idea, or you need to shift. Maybe you had an impossible goal. It’s hard in the dip. It’s the time when you doubt yourself, or your ideas, or both. Or you fear failure or you fear success, or both, because both will change you. These are times when you really find out what you can do.

Godin says if you’re on a path worth pursuing, you will walk into the Dip. If there’s no Dip ahead then you are not challenging yourself. You already have accomplished what you will accomplish on that path. And if you never experience the challenge of that Dip then you’ll miss out on the interesting, flexible work, yes, but most of all, you’ll miss out on the great feeling Csikszentmihalyi describes when work is at a high level of competence and engagement.

Sure, sometimes your Dip will come in an area that is not work – for example if you are training for a marathon. Usually, though, the time and energy we spend on our work is so great that it behooves us to look for opportunities that have a dip in them.

With the goals of work changing – from power to personal growth – the process of work will change as well. Work used to be about safety and stability and the Dip was for the risk-loving mid-life-crisis-suffering entrepreneurs. Today a Dip is the necessary path to the dream career where you can control your time and you can be engaged in work at the same time.

38 replies
  1. Andy Lee
    Andy Lee says:

    Dear Penelope Trunk,

    I’ve been reading your blog for a while now. you have a gift for describing these career paths. I’ve been blogging for the design school I’m attending and I just wanted to let you know that I will be linking to this post.

    Kind Regards,
    Andy Lee

  2. Mike Fisher
    Mike Fisher says:


    I’ve said it again and again, and I’ll say it yet again: your column is consistently excellent and one of the few items in the shifting sea of info that rates a daily click.

    Mike Fisher

  3. Avinash
    Avinash says:

    Hi Penelope,

    I’m wondering if you could share some of your own experiences in the Dip, and how you determined what was right for you and what wasn’t? Maybe then I could figure out whether I’m on the right path or not, since I think I’m hitting my own little fork in the road.

  4. Lee
    Lee says:

    A major difficulty is determining whether a risk is useful or foolhardy. A number of friends of mine have taken the leap of faith, only to crash and burn – some into bankruptcy – because they had bad business judgment: overestimating their abilities, underestimating the amount of time and capitalization necessary to achieve their dreams, inadequate market research, poor understanding of human nature, etc.

    When taking the leap of faith, it’s important to be surrounded by highly competent advice. We all hear about the Big Success Who Took The Big Risk – but not about the five other guys who lost their homes, nor the 90 percent of new businesses that fail in the first two years. I’m not trying to be a crepe hanger, just seeking balance: do the homework, get the ducks in a row, then take the risk.

    * * * * * *
    Here’s an idea: Structure your financial life so that you can give yourself the chance to fail a lot becuase we each learn so much from our failures.


  5. Daniel Dessinger
    Daniel Dessinger says:

    One thing is certain: I am not talented in all the things I wish I were and I’m gifted in some areas I could care less about.

    Example: Math – I’m really good at it, and I don’t care! Okay, I’m no Good Will Hunting and I couldn’t rewrite the Google algorithms, but I’m better than the average person at math. This comes in handy at times, but I have no aspirations involving the subject.

    Creative Writing – I desperately wanted to be great at it, but it has been the toughest nut to crack thus far. And not because I have no ideas, but because I lose interest two pages in (perfect for blogs, though).

    My only complaint
    You quoted Seth Godin. This guy drives me nuts. As far as I’m concerned, he’s 75% hot air and self-promotion. He coins phrases and writes books. Yay! I mean, boo!

    So leave out the Godin references and I give it a solid 4 stars.

  6. Guy Stratton
    Guy Stratton says:

    We met at the Olive Garden on Thursday afternoon and you delivered quite the therapy session to us all as to career development, and what we all really WANT.

    I find this blog to be right on. You mentioned to me that this book, the ‘Dip’, was the anti me. I would have to disagree…with some background…

    I am coming up on my 1 year anniversary as a Private Banker. This role has been exciting, and rewarding and I really look forward to coming to work every day. My dip, I believe, came about 13 months ago, when I was working in a lower level position with my bank. I worked in a fantastic branch with fantastic people. I had been there for 2 years, and didn’t have any plans on leaving. One day, my now boss, gave me a call and said that her boss asked her to call me and request that I interview for this position. At first, I was gracious, but told her that I would have to think about it…that I was very happy and couldn’t imagine being anywhere else at the time.

    I decided, as I have always done, to hear more. I have always felt that keeping doors open to opportunities will allow me to keep things on the upward and onward scale. Even if I am very happy at what I am doing.

    In the end, I made the hard decision to take the new opportunity, even though the position took alot more marketing, much more networking, and the occasional public speaking engagement…all of which I really didn’t have experience with…for the most part. This I believe was MY dip. Taking the chance to take a promotion that involved areas of expertise that I wasn’t yet exposed to…and I am thankful. I left a very comfortable job with great people and took a chance. My job now is now very flexible, I work with amazing people, and I have a client base that is fantastic.

    This may not be a earth shattering dip, but in my short career, I have really learned that I really enjoy sales, but moreso the people side of it. And the flexibility and the awesome perks that come with my job have really put me in a place that I just don’t know what else I would want to do….I guess we’ll just wait until the next dip!

  7. Wendy
    Wendy says:

    The first half of this post was great. It reflects my experience — that I have much more leverage negotiating for more time off and flexibility now that I’ve honed unique background and skills into a package that others recognize as valuable (there is no one else out there with my oddball mix).

    I disagree with the concept of the dip, however. I think every chance to get to this “flexible place” in one’s career is really more like an L.A. freeway “on ramp.”

    The challenge presents itself. And either you take it and accelerate to the next level (ie build on your skill set as Guy mentions above, and I did as well). Or, you let it go and stay in your comfortable place.

    For a while, in a new opportunity, the pace might seem fast as you’re learning a new job and honing new skills (just like getting on the freeway seems fast at first). But once you’ve made the transition, the comfort level returns and it doesn’t necessarily take more of your time or energy to do the new job.

    * * * * * * * *
    Well, as a counterpoint, I think what Seth would say is that comfort is boring. There’s not so much feeling of engagement and excitement.


  8. Jonathan Chew
    Jonathan Chew says:

    Hi Penelope,

    Thank you so much for this post. It’s the kind of insight that changes a person’s course in life for the better.

    For me, the hardest thing in choosing a career is picking something I am currently good at versus something I could be absolutely great at. No matter what others may say, it always boils down to my inner faith and courage to walk the uncertain road ahead. So thanks for your encouragement.

    * * * * * *
    Thanks for this comment, Jonathan. The difference between being competent at something and being great at it is so huge when it comes down to the options you have in life and the engagement you have in what you do. But it’s hard to admit when you are just good and not amazing. Hard for all of us.


  9. Andrey
    Andrey says:

    Hi Penelope,

    Our success depends on our leadership potential first, I believe.

    If a person is not an outstanding professional, it’s not as bad for own business, as a poor organizing level.

    Among those, who consider themselves to be good financiers and start their business with good professional advices will remain floating in 3 years only 5% versus 50 % of ones with good leadership potential!

    Thus, don’t forget to develop leadership potential first. This will make one confident, besides knowing, in his business. And luck often smiles to confidence too

    * * * * * * *
    Hi, Andrey. This is true if you want to grow a business that has a bunch of employees. But if you want to be a sole proprietor, you don’t need great leadership skills. Also, you can aim for a dip without having a business. For example, you could do oil paining, or you could run a marathon.


  10. Dale
    Dale says:

    It’s the seeming universal tradeoff, take the Dip or give in to your fear and play it safe. It all boils down to that.

  11. michael holley smith
    michael holley smith says:

    You’re on the right track. In my experience as a resume writer in half a dozen big cities over 30 years, I was constantly amazed how many people “just ended up” doing what they were doing, whether they liked it or not. The majority of people did not work in the field they had planned on (or got their degrees in), and the ones who really did well and loved their jobs were the ones who figured out how to match their creative characters at work with the possibilities of making better money and having more control over their work lives. And they all took chances.

  12. Tiffany
    Tiffany says:

    Thanks for encouraging people to dare to dream big dreams. It’s empowering when you really realize that you can achieve this flow in your life and career – whether it’s through learning a new skill or quitting something or simply believing in yourself. There truly are steps you can take now to help you end up there – €“ but they're not usually "safe" ones.

  13. Matt Bingham
    Matt Bingham says:

    What an interesting article and concept. You can either settle, or find a dip and take it head on. How many of us turn into drones at our jobs – some more visible than others but still drones. We go to work thinking we would rather be elsewhere. We get pigeon holed into the same type of thinking every day. Sure there are different aspects of your thoughts but it all deals with the same content. A great article and a great base of ideas to build on. Thanks!!


  14. Jon D Wilke
    Jon D Wilke says:

    I LOVE IT!! Penelope, thank you again for your constant encouragement. You are doing great things; keep up the good work!
    After a two-year hiatus, I am relaunching myself into a writing career. It is scary, exciting, fun and going great, but I know tough obstacles are approaching. To better prepare myself, I just finished “The Dip” for some added “oomph” to get through. While some readers may not like Seth Godin, I particularly like to read books and posts written by successful people and surround myself with other dreamers.

  15. Recruiting Animal
    Recruiting Animal says:

    A fun posting but not what I expected from the title. Bill Vick told me that he tried to figure out what separates “big biller” recruiters from the rest. The only common trait he could find was a fear of failure. Which sounds like an awful way to live to me.

    I thought that you were going to say something similar but, instead, you are warning that there is going to come a time when you have take a risk or change course.

    The quality of life in your model career seems to be defined by the pleasures of Flow rather than fear. The two are not opposed however if you believe that a fear of failure can push you onto a path of Flow.

  16. ClickerTrainer
    ClickerTrainer says:

    One thing I am uniquely suited to do, that I am good at, and that I enjoy, is being a web developer.

    That said, I feel entitled to make this comment: Underline your links. Not underlining them (1) makes people think (read Steve Krug’s book and (2) is not as readily accessible for sight-limited folks using html readers.

    just my .02

  17. Alan
    Alan says:

    It’s only appropriate for us to follow what is given to us. If we are good at singing, it’s clear that being a singer or any profession about singing is meant for us.

  18. d
    d says:

    This post resonated with me, a late-thirties, mid-career professional.

    I made a pretty clear-eyed self-assessment my first year in college, and decided to focus in an area that would make best use of the gifts I have. Fast forward 20 years: It turns out that I am exceptionally talented at my chosen profession (partly thanks to aptitude, but partly thanks to hard work). While I’m not getting wealthy at it, I earn a reasonably comfortable living, and have accumulated a lot of life experiences I would never have had otherwise. I’ve also enjoyed a lot of freedom and flexiblity: casual dress, largely make my own hours, and so on.

    At the same time, I’ve gotten to the point where said chosen profession is boring me to tears. My dip, I suppose.

    Well, after six years in a very comfortable and secure (and stultifying) position, I just gave notice at my company to take an “onward/upward” leap toward a huge, new opportunity. The new job still leverages my core skills, but it’s a move that “makes [me] scared of failure,” in your words.

    It’s worth noting, though, that this is really an exceptional opportunity. My “superstar” skill set is very specific, and I could go years without again finding a job like this new one…If I hadn’t stumbled across this job, I’d still be doing exactly what I chose to do–exactly what I’m great at–and I’d be miserable, except for the life comforts my job hsa brought me. This tells me that going with your aptitudes may not always be the recipe for career joy.

    Love your work!


  19. Fran
    Fran says:

    Great suggestions. Failure is our way of learning new things, but sometimes it’s better if we avoid failure just to be consistent with our output. We can’t risk our job for failing too much. Some of the learning should have been done as a preparation.

  20. learning how to play blackjack -   -  
    learning how to play blackjack -   -   says:

    Thanks for the update of your journey.I really appreciate the efforts you have made for this article. Self discovery is a vitally important aspect of any career path. Ask yourself, “What am I really good at?Whether you’re unemployed, going to school or working full time, we have all had to consider what career path we want take. Unfortunately, for many, not enough thought goes into this life-altering decision. Many of us end up in a career or on a career path that we don’t like, going through the same routine day after day and month after month simply because we are too frightened to make a change and try our hand at something else. If this sounds like you then it might be time to ask yourself if that’s how you want to spend the rest of your life and start believing that there is a way to achieve career fulfilment.These days, there is now a greater emphasis on personal skills, interests and qualities. Focusing on your internal feelings can tell you a great deal about what professions you are suited to. Also, importance is placed on developing transferable skills, that is, personal skills and qualities that you can transfer to each occupation you enter, then being able to refine them and ultimately form a match between the two to achieve maximum career satisfaction. So do not give up hope just yet

  21. downfromtheledge
    downfromtheledge says:

    This post makes me want to go work in a school again so that I can force every child to read this:

    “Your parents tell you that you can be anything, but you know what? You can’t….So one of the most important things you can do is come to terms with what you are uniquely suited to do , and what you’re not–and to understand which is which.”

    A resounding YES!

  22. Caroline
    Caroline says:

    “It is clear from a wide range of polls that the majority of both men and women under 40 are willing to give up power and money to get flexible and interesting work. . . .Taking a low-paying, unimpressive job is not going to give you flexibility. In fact it will probably put you on track to be serving fast-food on a schedule that is so inflexible you have to negotiate with six people to cover your shifts during vacation.”

    Funny and true! I just read another article about an inverse relationship between ambition and relationships, but it seems like there’s got to be a happy medium. If you’re ambitious enough to be great at something, then hopefully you can find an interesting and flexible job that will allow you to spend time with your family.

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