The old paths through adult life don’t work anymore. Graduate school is no longer a ticket to a stable career, and in some cases, it’s not even a ticket to a job. Student debt weighs so heavy today that people should not expect to have what their parents have. Technology opens up many types of new types of unstable careers, but slams the door on many stable ones.

Workers today will have no fewer than three careers in their lives, and they will change jobs frequently when young. After that, they will cut back when they have kids, ramp up when they need money, and switch when their learning curve flattens.

The good news is that a large consensus of experts say in today’s world, this kind of living will not necessarily hurt your career. And in fact, changing positions frequently makes you a better candidate in many circumstances. Jason Davis, blogger at says, “If a candidate has been at the same company for 10 years or more, you should take a red marker [to the resume], draw a big x through it, and throw it in the garbage.”

Today’s worker focuses on finding positions–all the time–that are fulfilling, engaging, and accommodating of personal time. It’s a nice picture, but it’s hard to imagine it’s a stable life.

And, for the most part, people do not like instability. Even the people who you’d think would be risk takers, entrepreneurs, are not, really. Most people are thinking of ways to mitigate the risks they are taking, according to Saras Sarasvathy, of the University of Virginia Darden School of Business.

So what can people do today to mitigate risk in the face of an inherently high-risk workplace? Get good at dealing with transition, because today’s workplace is full of it. The people who are most adept at dealing with transition are the people who will do best in their career and in their life.

1. Have two jobs at the same time.
The easiest way to make a transition is to do it slowly. The old way to change careers is to quit one, leave everything behind, and start everything over new. This is extremely difficult, and extremely risky. An easier transition is to start a new career while you’re doing the old one.

In some cases, you will end up doing the new career most of the time, in some cases, you will find out you don’t like the new idea and you’ll try something else. Recently, though, some people find they like doing both. Two careers makes sense to a lot of people, especially if one is fulfilling and the other pays the bills. Or one is very unstable and one is stable.

Marci Alboher describes the nuts and bolts of having two careers in a way that works in her new book, One Person/Multiple Careers: A New Model for Work/Life Success. She moves between her own set of careers as author/lecturer/writing coach as she tells a wide variety of stories of how people maintain multiple careers successfully.

“It used to be that the only way to transition was to leave your prior career behind. Today’s strivers are learning how to take what comes before and overlay new experiences on top of that. Today a career can be a mosaic.”

Alboher shows this is a path people can use to not only create more stability as they change, but also to follow their dreams as they’re going.

2. Be comfortable with uncertainty.
Eve Ensler, author of the play The Vagina Monologues and also, more recently, the book Insecure at Last:Losing It in Our Security-Obsessed World, thinks one cause of insecurity in our lives is the expectation of being secure. “If you think you’ll get to the point that you’ll be secure, then you’ll be chronically depressed,” says Ensler.

Since we can never really be secure, we should instead learn to be comfortable with that. Getting good at dealing with a world that does not provide security is actually a more healthy way to live than trying to find that one, perfect path through life that leads to a mythical security.

Ensler’s ideas suggest that today’s career paths, that wind and stop and turn and surprise us along the way, may be better for us once we get used to not knowing what’s ahead. “When you start working with ambiguity and living with it initially, it’s scary because there are no signposts. But eventually it seems to be a much more interesting way of living.”

3. Take time to explore.
It used to be people started exploring when they turned 40, and we called it a mid-life crisis. It seems clear, now, that exploration and self-discovery is something to do throughout life, not just when you get sick of your mortgage or your marriage.

But this process requires we take time to check in with ourselves during transition times. Jumping quickly from one thing to another is not as effective as taking time to figure out how you’re feeling, and what you enjoy, each step of the way.

Mike Marriner was planning to go to medical school but realized he wasn’t passionate about biology. He decided to take time to figure out what he should do next.

During this process, he started Roadtrip Nation, which sends teams of students around the country to interview people about their lives and careers. The idea is to provide inspiration or cautions for people as they consider making a transition. “Today there is no transition period,” says Marriner. “Everything is very quick and we are trying to put the spirit of exploration back into American culture.”

Roadtrip Nation has become a book, a summer program for college students, and a PBS Series, all addressing the idea that transition is serious business, and part of moving into adult life is getting good at figuring out where to go next.

To many people, the continuously shifting workplace is disorienting and discouraging, but really, you just need to reorient yourself and develop personal tools for a new workplace. Transition is an opportunity, and today life is full of more opportunity than ever before.

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20 replies
  1. Tim
    Tim says:

    Another great one Penelope… couldn’t agree more.

    This issue of obsession over security goes well outside the realm of careers of course, but that’s probably an article for another day.

  2. peter vajda
    peter vajda says:

    change, ambiguity and uncertainty…it’s no surprise the NIH reports major spikes in mental health statistics around depression, addiction, obeisity, etc.- psysiological, emotional and mental reactions to change, fear, unhappiness.

    I find that coaching folks to consciously explore inside, to look at what really, really, really, supports true harmony and balance, core values, is a positive, supportive and effective first step at understanding, and being able to accept, instability, change, and uncertainty as opportunities.

    When folks are at the top of a roller coaster they can scream with fear or scream with excitement. It’s the same energy; we just interpret it as one or the other depending on our past and how we were taught to deal with risk. The job market today is one such roller coaster.

    Doing the necessary inner work to learn how to scream with excitement allows one to view risk and uncertainty as a journey, an adventure, to be “OK” with “not knowing” and allow the energy of fear or uncertainty to propel one forward with strength, courage and intentionality rather than keep one stuck or paralyzed.

    Your advice to step back, do some conscious self-exploration, and develop personal tools can certainly support one to experience harmony and balance, to gain clarity on both their short-and long-term visions and live in a place of change and uncertainty with positivity.

    Jumping from one thing to another usually results from a fear-based approach, or “unconscious”, reactive approach to life and living and almost never results in inner peace, harmony or balance. For these folks, yes, mid-life crises begin at 25 and really never stop.

    Transition is serious business and those who face it, explore it, proactively will be all the more comfortable, inside and out, with the uncertainty that accompanies the experience.

    * * * * * *

    Peter, here’s the problem I see with all this stuff you wrote: I think you misunderstand job hopping and constant career transition. These trends are a result of a strong, deep commitment to be true to oneself. Not about fear.

    You write about the journey of learning about oneself, etc — I think that is the journey people take through the constant career transitions that are happening today.


  3. Emily
    Emily says:

    Great thinking, Penelope, and very helpful – and validating – for what I’m going through right now.

    Re. what Peter Vajda said: “Jumping from one thing to another usually results from a fear-based approach” – isn’t it more true that staying in the same job forever is fear-based? I think my colleagues from my former job are still freaked out that I left behind all that security…

  4. peter vajda
    peter vajda says:

    Emile, yes, and thanks. I should have said “unconscious” and reactive (and perhaps left out fear-based) The fear of the unknown, risk, and moving out of one’s emotional, psychological, and mental comfort zones is what keeps folks stuck, paralyzed and in a “faux-rational” mindset of why I need to stay where I am, almost like it’s not a choice but a “passively-imposed” obligation.

  5. Erik
    Erik says:

    Peter – I’ve read over your comment a couple of times. I still can’t figure out what you’re actually trying to say – though you clearly have a great vocabulary. I think you’d be more suited to poetry than giving people career advice, though. If it wasn’t a Sunday, no one would even have time to read your poetic advice, let alone try to figure out what it means.

  6. Deborah
    Deborah says:

    Very nice advice if you are not over 50. When you are that age, you say you want to change and advisors tell you do something similar to what you’ve already done in life, even if it hasn’t worked out. I feel like I’m going to be stuck selling donuts or at Wal-Mart with a Master’s Degree.

  7. Deborah
    Deborah says:

    Oh, and I forgot about the mortgage and the husband losing his job soon, too. What is your advice to that?

  8. Jacqui
    Jacqui says:

    Taking time to explore and embracing uncertainty are very romantic ideas I’m sure we all think we’d like to enjoy. That’s originally why I chose to work in the political arena. It’s always changing, and no two days on the job are alike. Working in politics is my true passion.
    Last November, I left the political arena (the 80 hour weeks, living on greasy pizza, and impossible deadlines that I love) for a much less political 9-5 job. There were moments of near emotional breakdown as I contemplated that I had just left the one thing that I felt defined me.
    And then … I realized that for the first time in my life, I knew I’d be able to pay my rent, my car payment, my student loans six months from now. And this amazing peace came over me.
    I know that I will not keep this job forever, but I also know that stability is not a new dirty word. It’s a beautiful thing. And those who seek it are not foolish or unhappy – just sane.

    * * * * * *

    This is a really important comment. It makes me wish I had been a little more clear in this post.

    I think what Jacqui writes about stability is so true. Stability is important. The stress of instability has made for some of the hardest, most unproductive times in my life, and I’m a big fan of making decisions that lead to stability.

    The reason I wrote this post is that I think it’s very hard to find stability in a career today. For one thing, old stable paths don’t work. And the other problem is that no job is certain to last. The only thing that’s certain is transition. So, in my own quest to make a more stable life, I have found that getting good at transition makes me feel less unstable.

    At any rate, Jacqui, congratualations on getting yourself to a spot where you know you can pay rent. I have first-hand knowledge of what an incredibly huge relief that is — a way bigger relief than finding one’s dream job.


  9. Anastasia
    Anastasia says:

    A frightening thought. No roller coaster can last forever, and if it did no one could ride it. Sounds to me like a recipe for Depression and unionization in a decade or two. And that’s coming from a twenty -something art student. I think transition is fun. But I also think that too much chocolate cake will make anyone sick, and the more often you have it, the less it takes.

  10. weelbaro
    weelbaro says:

    I used to be a technical project manager. 18 months ago as I was reluctantly driving to my job that paid 30K for the type of workload that I made 80K for 5 very, very, very long years ago, I decided that I’d had enough.

    Now I scrape by at an IT helpdesk asking people if their system is plugged in when they approach me w/ a system problem. I do this so that my evenings will be free for my secondary, secondary education. I’m currently enrolled in a web application development program. I enjoy doing the work, and like the hope of a better day through career transition … BUT … there is something to lose in all of this.

    I’m not really looking forward to a brave new world of constant career re-education or supplementation. I need more than a career focus to feel whole, yet my current career and my future career is all I have time for. Things won’t change over time as, by the time I”m ready for full fledged application development, the rules will be changing again, as is the case w/ most industries these days.

    I used to read voraciously. I got lost in good books. I know a little something about most subjects and enjoy learning about whimsical things. In our wonderful world of transition, I’m forced to kiss that all goodbye. I don’t have time for it. I can’t see how this is something to be relished.

    * * * * * * *

    I really appreciate the honesty of this comment. The truth is that it’s a lot of work to always be learning new things. Some times in life are better than others for continuous learning. Some times in our lives we just want to get by. Those of you who think this will never be true of you, it’s probably because you’ve been very lucky. But no one is lucky forever. So, what I mean here is that I have emplathy for the problem laid out in this comment. 

    But look, the good news is that the new, relatively unstable workplace rewards people who are curious and love to learn. The bad news is that if you are not curious about your particular field, then having to learn new things all the time will be really annoying. So maybe what you need to do is figure out how to start doing work you enjoy learning about. So maybe web application work isn’t the right thing for you to go into if you don’t enjoy learning about it.


  11. Working Girl
    Working Girl says:

    Deborah, Your advisors are giving you what they think is “safe” counsel. You most certainly can change your life, even after age 50. I did. I think Penelope is right in that there is no such thing as permanent stability any more. If there ever was! In my experience, periods of stability and calm are just that, periods. They are bracketed by bouts of upheaval, opportunity, stress, possibility, challenge, and stark naked fear. I.e., change.

    When we are in the change parts of our lives, we might not appreciate being told that (everlasting) security and stability are illusions. Then again, we might find this oddly comforting. I did.

    I happen to think that—whatever change scenario you are now living through—you are smart enough to figure it out.

  12. weelbaro
    weelbaro says:


    In response to your …er…. response. I both agree and disagree with you. I think the current and future workplace does and will reward curiosity and a love to learn.

    I really enjoy the challenges of learning new things about object oriented programming languages (how nerdy do I sound!). I guess the point that I was trying to make, is that change in the workplace can be so all consuming that I personally find it cutting some other areas of my own personal knowledge and growth that I used to enjoy. There’s no money in Japanese Haiku, or knowledge of Shackleton’s bravado below the 60th parallel. I like to be well rounded, but feel like I’m being pulled from that reality. I always said that my soul was sent to the wrong planet because 24 hours just isn’t enough.

  13. Davey
    Davey says:

    I’m curious…where do you go to research your writing material? Better yet, have you thought out the material and advice you offer, or at least speak from experience?

    For instance…where did you find Jason Davis, whocm you quoted in your article, and do you actually believe his nonsensical, illogical and out-in-left-field thinking that he espouses?

    So according to this clown, if someone lists having had more than 10 years of experience at a job, you (the recruiter) should put a big x on their Resume and chuck it in the garbage? Really? How insightful, or should I say inciteful!

    So, being at a job for more than 10 years is a no-no, well then, I guess whoever decides to look at Jack Welch’s (ex-CEO GE)resume should do just that – except that he is happy getting millions from Business Week as a Columnist. Regarding Bob Nardelli, now that’s a different story. Or I imagine Microsoft should can Ozzie ___, the former CEO of a MASS-based software firm, because he was at the company he founded for more than 10 years.

    Perhaos, Ms. Trunk, you should take a bit more time to research and qualify the material you add in your column – lest you find yourself out of a columinst position at thg Globe, and start looking for another job yourelf.

    Now, how long have you been working in this capacity for the Globe?????

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