How to manage a career right now


I have never been great at picking my own clothes. I’m great at interior design, but I have a blind spot for clothes. So I email Melissa photos of my outfits, and she uses her photographic memory of my closet to edit my outfits.

When I sent her this photo, she said: “What is this?”

I only wanted her opinion about the color of the shirt, so I thought it was okay that it was blurry. But the more I look at the picture, the more I think that it’s how I feel about myself right now.

I am not quite sure who I am, right now. And given the current career climate, this is actually how most people see themselves, too—blurry from constant movement, settled on the basics, but unclear on the specifics.

And then I read an article in Fast Company this month titled Generation Flux. The article is about how careers are constantly moving and our identity is therefore moving as well.

So I am focused on how to make myself more clear about what I look like. At least right now. And here are things I think we each need to do to pin down our moving-target, career-jumping selves.

1. Get a plan for post-35.
This is a great post by Matt Heusser, from Google, that outlines why you only have fifteen years to put a plan together. By the time you’re 35 you have to get out of any career space that is for young people and settle into an older person job.

Want to know what young people jobs are? Making sales (as opposed to managing), writing code (as opposed to managing), working across three time zones. These are jobs that middle-aged people do not get. Mostly because no one would respect a person who has worked for 15 years and still has to take a job like this. These are not good jobs for having a life. These are jobs for working long, hard hours with the intention of laying the groundwork for a better career.

Sara Horowitz, writing in the Atlantic, suggests that the new jobs will be independent, short-term and maybe even coffee-shop based. Others, like Cathy Benko at Deloitte, suggest there will be a series of lateral moves that will somehow become respectable. Anya Kamenetz, writing in Fast Company, says this will look like continuous, back-to-back career change, so that job hopping begins to look tame and totally normal.

At any rate, you can’t get through the second part of your career doing the work you did in the first part. So there is not time to rest in a safe spot for your career.

The other reason you only get 15 years is that your salary tops out in your late 30s. (Actually, age 35 for women and 40 for men.) Statistically speaking, you are extremely unlikely to earn more than you are earning at that age.

2. Get good at setting boundaries.
In the old workplace you could take one job, on an established path, and move forward in a predictable way. The average job today lasts four years. (And other research shows that people who are staying a lot longer than four years are probably getting themselves into trouble.)

If you are changing jobs every four years, you are going to have to manage lots of close relationships with co-workers and bosses. This requires being very good at setting boundaries, which, in turn, requires good self-knowledge.

I have a bookshelf full of boundary-building books right now, and I’m blown away by how relevant they are to careers. (Examples: I Hate You Don’t Leave Me and Stop Walking on Eggshells).

Most of our career problems have, on some level, a boundary component. For example, many people in their 20s know what they’d like to do but they cannot separate the dreams of their parents from their own, and so they make bad choices for themselves that they spend a decade undoing.

In other cases, career choices are clear and good, but a spouse has dreams that are incompatible with this choice. For example, the spouse wants a income, or more attentive child care, or a relocation that is not possible. In this case there would need to be a family talk about boundaries and how one person’s dreams cannot depend on impossible career feats by the other person.

The better we are at managing boundaries in our personal relationships, the better we’ll be at managing our career decisions. And as careers become more dynamic, this equation becomes more true.

3. Get tons of coaching.
I have always been a huge fan of coaching. It’s not only that I have hired people for help with what to wear. In fact, I think one of my biggest strengths is to get coaching from a wide range of people.

As a result of realizing this personal strength, last year I started doing a lot more coaching for other people, and I started reading more about coaching as well. For example, all high performers get a lot of coaching. And the need for coaching does not wane as you get better and better at your job.

So many people told me that the coaching session I did with them changed their life that I decided I wanted to get that. I wanted a coaching session that changed my life. So I asked Christine Carter to do a coaching session with me. She wrote the book Raising Happiness: 10 Simple Steps for More Joyful Kids and Happier Parents. She coaches families on how to create systems that promote family happiness. She helps them restructure schedules and priorities, which are exactly the things I’ve been having trouble with since I moved to the farm and started homeschooling.

We dealt with fundamental decisions like when I will do my work each day and how the family can be more predictable. And you know what? She changed my life. Because she took questions that are difficult and complicated for me and she was able to find good answers quickly. Which, by the way, is exactly what I am able to do when I coach people about career decisions.

A coach works on the same problem with hundreds of people, so the coach is great at seeing how to solve that one problem for you. For anything. I’ve written about coaching for mental imaging, coaching for more optimism, coaching for gait. Each of those coaches have blown me away by teaching me something totally new about myself and helping me solve problems related to that area.

So I can’t stress enough how much I recommend that you get coaching this year. You cannot rely on your company to teach you what you need to know to manage your career. Because first of all, no one knows that answer except you. But also, a company cannot make that kind of investment in employees when the average tenure is four years.

And one more thing about coaching: It’s very hard to know what question to ask. Which may make you think that this is a reason to not get coaching. But in fact, learning to ask good questions is something you can get coached for as well.


79 replies
  1. Erin
    Erin says:

    Stop Walking on Eggshells is awesome. My mother has BPD. I am guessing you are reading these because of someone other than your parents but I also reccommend “Toxic Parents”. Changed my life and my career. :)

  2. Amy Parmenter
    Amy Parmenter says:

    You know why you are a good coach?? Because you are a good mirror! I see myself in you – but, somehow, it also makes me see myself differently. I think it’s easier to look at other people than it is to look at yourself. You help people see things in themselves. Mirrors are important.

    Amy Parmenter
    The ParmFarm

  3. Hope
    Hope says:

    View from the dinosaur age of 58: Made my best money between 44-50. Did sales management and HATED it. Am now doing a sales job (horrors!) in an industry I know intimately. Pays more than the last job, and I have a home office with LOTS of flexibility. Couldn’t be happier. Hope to retire in this position, if only because it leaves so much of brain free for whatever pleases me. Biggest challenge: Subjugating my ego and getting along with some real idiots. BUT, I have freedom, income, and benefits. In this economy, at my age, nothing to sneeze at. All that said, I totally agree with your advice on boundaries and coaching. Have learned the former and used the latter throughout my career. Times changes, but basic human skills don’t. Bon chance.

      • karelys
        karelys says:

        the thing about stats is that they are the opposite of inspirational stories.

        statistics tell you where you’ll be if you act like the majority.

        the truth is, we are not all made for the success stories that inspiration boards/videos/speakers shoot at us.


        not all boys in a wheel chair end up in olympic basketball.
        not all people make the best money of their life during their 44-55 age bracket.

        i would say that Hope makes that much money because she’s smart, she’s the difference, she’s the alternative story.

        For me stats work because it helps me see down the road, where I’ll be if I don’t change my course of action, alter my attitude, etc.

    • Anna
      Anna says:

      Thank you Hope. That is very reassuring. Just like knowing that when you get old you don’t HAVE to get an ugly perm, be interested in nothing but what’s in TV and walk an ugly little poodle all day long. There is space for individuality, talent and variation.

      • Hope
        Hope says:

        For the record I went through the ugly perm stage in the late ’70s. LOL. And not to brag on myself, but if you met me, you wouldn’t know I’m almost 60…I know this by the look on people’s faces when they hear my real age. And I haven’t given in to gray hair or big weight gain. Image means a lot in the work world, whether we like it or not.

  4. Tina
    Tina says:

    Coaching is VITAL. As for asking good questions, that’s certainly important–but a good coach also ‘draws’ the questions and information from their client. This makes the conversation one that expands from one place and spirals outward rather than the coach simply being a sounding board. Since pretty much anyone can call themselves a coach, it’s also important to make sure the person coaching has some experience in the area you want coaching in–some measure of success. (I would advocate this in all areas actually–from doctors to dentists to financial planners. They don’t need to be perfect, they just need to be credible.

  5. Alyssa {Second Floor Living}
    Alyssa {Second Floor Living} says:

    I’m fascinated by this idea of “young people jobs” and job hopping as the new norm. I’m personally working in a very “young person” job right now (ad agency account management) where people burn out quickly, and I don’t think this assessment could be more true.

  6. therapydoc
    therapydoc says:

    I was looking for DaMomma’s blog, which has moved, but she links to you, and wow, what a find. The stuff about how you (we) try to protect our things from the reality of life, just priceless (as is electricity).

  7. Heroine Worshiper
    Heroine Worshiper says:

    Middle managers still work their asses off, 7 days a week. People over 35 seem to be the ones with the least free time.

    • WorkingMom
      WorkingMom says:

      I do agree to some extent with Heroine Worshiper that it’s the over-35 middle management crowd who still work the same long hours, perhaps because they have more responsibilities. Now that I have my own almost-adult, my advice is that no job is secure, so find something you like doing that let’s you put a roof over your head and food on your table while providing you a great quality of life. Like the parable says, no one ever looks back at the end of their life and says, “Gee, I wished I’d spent more time in my office at my desk”.

      • Nina
        Nina says:

        That’s what I am trying to do but since it does not pay much during start up I also have to keep my regular job. I enjoy my regular job, but it is not secure! Many long hours trying to start up something. Wish I could invest 8 hours for my own thing, not only my regular job. But at least I’m enjoying it. Will not look back and say “I didn’t try”

      • Jen M.
        Jen M. says:

        I’m in the same position as Nina. I started business in 2008 and am struggling to grow it. Meanwhile, I have to keep a day job to keep my family housed and fed. My BF also has an income, but we’ve done the math and can’t get by on one income, so here I am.

        That said, I’m looking for a less obnoxious day job.

  8. Can't stop watching
    Can't stop watching says:

    The photo is IMO gorgeous. Very artistic; it looks almost as if you had painted it with watercolours.

    It takes courage to realize that sometimes things are only beautiful if viewed through a film. Deciding to live in sharp focus is not easy. But blurriness can convey an impression, an image or a sentiment – not information or opinion or guidance.

  9. Penelope Trunk
    Penelope Trunk says:

    @ karelys (I don’t know how to make my comment nest under the comment from karelys — scroll up a bit to find it)
    I like how you say that statistics tell you what you’ll be like if you act like the norm. That’s true. But I think so often we think we are not the norm but it is the norm to not be the norm. Because no one is the norm. It’s an Escher puzzle or something.

    But now I’m thinking that seeing statistics like the ones about pay topping out at age 35 — that inspires me to take risks that look totally insane. Because if the norm is to not be the norm than to beat the norm you have to be so far off the norm that people think you are nuts and doomed and write you off.

    Oh. Maybe being written off as insane is a career badge of honor.


    • karelys
      karelys says:

      i read it so many times until i went cross-eyed! ;)

      here’s my image of it, we’re on different boats (everyone is different) but on the same river. if you just go with the flow you’ll end up on the rocks. If you navigate correctly you may avoid rocks, the precipice, and actually shave off hours of floating so you enjoy the destination and not have to convince yourself that it’s about the journey.

      i hope that makes sense.

      i too like the stats so i can avoid the grind that everyone seems to go through. but i can’t seem to figure it out. i’ve figured other things out, much of it has to do with reading this blog.

  10. Mark Wiehenstroer
    Mark Wiehenstroer says:

    I think the color of your clothes are matching based on the advice and use of the color wheel described at this site ( ).
    I really liked the Fast Company article on Generation Flux as it points out that this generation description doesn’t include any age parameters. It’s more about mind set (i.e. – open mindedness and adaptation). The article reminded me of your blog post – – in some respects.

  11. Anna
    Anna says:

    This scares me… ‘by this and this age, you have to have done this, or you are stuffed’…

    Hopefully it applies to people in traditional careers only who don’t have too much drama in the past history so they managed to get through all the right career checkpoints by all the right ages. Hopefully there are alternative ways to not be stuffed, too.

    • MM
      MM says:

      “You have to by ___ or else ____” is, in my opinion, always bunk. There are no rules, but strong opinions make page hits and sell ads.

      • Jen M.
        Jen M. says:

        I tend to agree. We are all different with different skill sets, different experiences, different support networks (or without one in some cases,) etc.

        I still thought this was a good article, except that coaching is so damned expensive it’s not an option for me. I’m sure I’d benefit a lot from it, though. Such is life!

    • karelys
      karelys says:

      i think it’s more about “well, if you want to be this age and working on certain positions you better accelerate the pace” type of thing.

      do you think that someone that has been dinking off in entry level jobs will be qualified or have the references to land an amazing job where you have to oversee many people and also make bank?

      most likely no!

      and as for work out of corporate america i think is very much the same. many of the most successful bloggers already had years of experience working for magazines and other publications, or they have something that brings incredible value to their blog or whatever business they are taking off the ground.

      the first response says that these opinions are bunk. but i think they make much sense.

      now, if you’re older and don’t invest time and money cultivating yourself on classes and gathering of knowledge on the side (things that your job may not offer) you’ll gather tons of experience on your one job and then that’s it. you won’t be able to just hope onto another track that may be too different from where you’re at.

      someone named Hope posted that she was in sales and made the most money between 45-50.

      but i think it’s way different when you have a certain type of job by choice or you feel stuck there.

      i’m 24 and i feel stuck in my job. i’m trying to get great at sales because i think that no matter where i turn i can always have a paycheck from that. i want something else but i have no experience, just 5 years in the ins. industry. and so i’m stuck.

      can you imagine my office manager that has been here for 15 years!?

      she’s 39 and has loads of knowledge which make her super valuable but i don’t think she even breaks the $17/hr mark. she’s stuck. unless she grabs a job at office management or greeting at walmart. i guess stuck going up.

  12. Katy
    Katy says:

    I totally disagree with people over 35 not being considered for coding positions. Who said that every dev should/want to be a manager anyway?

    • Daniel
      Daniel says:

      Absolutely – I earn (well, let’s just say a lot) as a software developer, and I just turned 40. Granted, I do a lot more than pure coding – software design, requirements review, etc. but Penelope’s post is yet another example of people assuming and even promoting the idea that once you’re a certain age, the only way “up” is management.

      I out-earn everyone short of a VP in my company and I love my work. Granted a) I’m very good at what I do (sorry if that sounds conceited, but it’s true) and b) this story isn’t typical. But I could say that people with Aspberger syndrome are incapable of holding outward-facing roles in a company. Generally that might actually be true, but draw a line in the sand is pretty silly.

      • karelys
        karelys says:

        you just mentioned the one detail that makes you “not stuck” like everyone else that could be in your situation: you do more than just coding, you’re good in many other things.

        and that takes effort; to get good at different things. not only innate ability but being proactive about learning different things.

        so her argument is actually true. if you were just a programmer you’d have to be in an environment where not even the young people are at least as good as you to be able to outearn everyone.

  13. Gwen
    Gwen says:

    Interesting stuff. I’ve been getting that feeling about the coaching for a while now. Definitely something I need to look into… first things first, I’m 23, trying to look professional, and have absolutely no clue how to put on makeup. Ack. Any recommendations on where I can hire a “Apparently I was never a teenage girl” coach? I guess I could just walk into someplace where they sell it and ask for help, but I feel like the employees would be trying not to laugh…

    • Yvette
      Yvette says:

      @ Gwen – makeup artist will be more than happy to help you, believe me. They will see a nice canvas to work on.
      So go ahead and pass by a nice department store and enjoy the free makeup lesson-you could buy a tinted mosturizer or some other not too expensive item.

      • Gwen
        Gwen says:

        Thanks for the encouragement. I guess I just need to swallow hard, do it, and not care if they are laughing at me. I’ve been trying to get used to not avoiding uncomfortable sbut necessary social situations, so I guess it could be good in more than one way?

        I think I’m going to stop by the Jenner’s near us after work tomorrow.

    • karelys
      karelys says:

      honestly i google stuff and youtube tutorials ALL THE TIME.

      also, i go to expensive clothing sites and see their “look books” on the “professional section” or “office wear.”

      There are slideshows in vogue, marie claire, etc. or just read blogs.

      Then I see what applies more to my situation and personality then i got to target or goodwill (thriftshop in town) and get my budget version of everything.

      I don’t wear much makeup but sometimes i can step on the side of “too little makeup” which i don’t like.

      also, i pretend i’m communicating something with my apparel so i go by what i’m trying to communicate :)

      hope that helps.

      also, makeup counter people will try to sell you TONS of things that you will barely use yourself and will take you like 20 minutes to put makeup on.

      just use tried and true methods and then add little by little: eyeliner, sometimes eyeshadow, etc.

      the fastest way to look presentable for me is black everything, just foundation, mascara, tiny bit of blush and red lips. oh and tight my hair in a bun.

      i can be done getting ready in 10 minutes.

      • Gwen
        Gwen says:

        Thanks for all the info. YouTube is sounding pretty good. I think I’ve developed a pretty good professional dress sense, although it’s a bit masculine. (What can I say, I love cufflinks.) I guess part of the problem is that I’ve always avoided those magazines like the plague. I should get over it. I’m not going to start reading Take a Break just because I look to Vogue for makeup tips I suppose…

        I wear my hair in a bun right now too. It’s not very flattering, though – I only wear it tha way because it’s so long that I can’t do anything else without it being horribly tangled. I think I’m going to get it cut much shorter soon. Haircuts, that’s another thing to start looking up! It’s makeover time…

    • Kristin
      Kristin says:

      I would walk into Ulta and find a stylist whose makeup looks appropriate for work (not too dark or sparkly) and ask her. They will show you how to apply it. You can also buy kits that teach this. There are also tutorials on YouTube. I was (or am) in a similar position, except that I had the look down for work, but not for social occasions.

      • Gwen
        Gwen says:

        Man, I don’t even want to think about the fact that I’m supposed to be able to do different kinds of makeup for different situations! Luckily (in this sense anyway) my social scene is mostly still freaks and geeks, so in social situations it’s fine to have no makeup, or goth-eyes and blue hair, or… I guess I should get ready for social situations with colleagues etc though… everyone knows me as the token strident feminist so I’m sure they’ve taken my lack of makeup as a statement so far!

        I’m in the UK, I don’t think we have Ulta here. But I think I’ll look around for an equivalent. I guess that would be walking into the cosmetics department of a large Boots or something. Or maybe a store like Jenner’s or Debenham’s. Ehhh, youtube is definitely starting to sound good…

    • karelys
      karelys says:

      you know i’m 24 and been employed as insurance agent for 5 years now. my first few years had zero training. so really, not much help experience wise.

      but lately, rather than totally making a career change (i want to be in psych anyway) and try new everythign and new education i’ve been making lists of the skills i’ve gathered.

      many of them are “soft skills.”

      and i’m repurposing anything i can get my hands on. i love chandeliers but they are super expensive (easily $6000 for a beautiful one yikes!).

      rather than longingly looking at websites with light fixtures i can’t afford i decided to use my basic knowledge of electric work and tons of google, youtube, and blog tutorials to work. I’m in the process of creating beautiful things without breaking the bank.

      let me bring all this full circle by saying that if you don’t want to be where you’re at and just getting a different job is not as easy as some have it maybe you can start making lists of skills you’ve gathered and start “repurposing” all those years of experience.

      maybe with a little bit of this and that you can create something that is different enough to satisfy and bring a fat paycheck but also similar enough that all those years of experience won’t be a waste.

      at least that’s what i’m trying to make work with me :)

      • Jen M.
        Jen M. says:

        Yup. Also, freelance on the side.

        That’s what I’m doing. I pay the bills as an admin, but on the side, I am a photographer and a reporter for a local blog. I’m rocking it–the money’s just not coming in yet; however, I am leveraging those skills and that experience in my job search.

        When I can figure out funding, I’m probably going to go back to school and get my bachelors in journalism.

        Who cares that I’m in my early 40s? I don’t!

  14. dianna
    dianna says:

    After waking up wanting to puke for five days, I just got out of a direct marketing business. I messaged my 16yo dtr that I couldn’t bring her lunch because I had to fax a letter to these people to get my money back. She expressed her disbelief that I had ever considered sales by texting “HA you hate people!!!”
    My point is this (very bright) 16yo knows more about me than I do myself.

  15. Alan Taylor
    Alan Taylor says:

    I have a professional degree – civil engineering – and 30 years experience in that field. It’s hard to see what different work I could do and earn so well. What is the advice for those in regulated professions – doctors, lawyers, engineers – who worry about the effect on their families of a major drop in income?

    • MM
      MM says:

      Nothing is guaranteed for anyone anymore.

      If you are a lawyer or doctor, in private practice, you are your career and are just supposed to keep selling services, getting projects, and making money. You “should” be making more after 35 or 40 because you have more skills, more contacts, and are generating more work. If engineers are tied to employers I have no idea what they do. Become consultants?

  16. Harriet May
    Harriet May says:

    I think I am having my quarter life crisis. I am sure I see myself as blurry, but also I can’t help but see where I want to go as blurry too. And how can you get from one blurry place to another? It’s impossible. I think my relationship is falling apart, and I think it is a bad time for that to happen. I think I don’t have enough friends, enough connections, enough experience, enough drive. My dad thinks he’s dying, and my mom thinks she can’t pay the mortgage without him. I think I want to go somewhere else. I think I’m finally going to run a marathon this year.

  17. Yuse Lajiminmuhip
    Yuse Lajiminmuhip says:

    P, I am still in the phase you described earlier where I have the choice between getting married or making money (I am focusing on the latter) and I like to think that I have a pretty good life/career plan set up. The problem is I actually want to get married by the time I’m 30 and my lack of experience in the whole marriage thing (my parents divorced when I was young) makes me think that maybe my plan will fall apart once I bring in the spouse.

    Am I to expect my flying-solo plan to crumble once my situation turns into a two-person affair? How can I “plan” for the unexpected?

  18. terri
    terri says:

    Speaking of coaching, I liked reading thoughts from one of the documented best coaches, NBA Bulls/Lakers great Phil Jackson. His book- Sacred Hoops: Spiritual Lessons of a Hardwood Warrior

  19. Gordon Chen
    Gordon Chen says:

    These days inspirations and advice can be found everywhere, when you’re ready to be coached a coach is great otherwise advice can be found from books, movies, blogs, friends, google, youtube, this blog etc…

    just need to be careful who the advice is from as some people are good at preaching yet not so good at practising what they preach, whilst there are also great coaches out there :)

  20. Victoria
    Victoria says:

    P – And yet no mention of a pleasure coach. The holy grail for type-A, can-do people (read: Americans) is a real sense of happiness and satisfaction. And why is this? No matter how much is accomplished there always seems to be the “if I had more or did more…” gap. My view: many live with a disconnect to body and conflicted feelings about sensual pleasure. And so the contant (disconnected) search for the holy grail comes up short. I believe sexual energy is behind much of what we do – and yet, many are taught to deny or compartmentalize it. I think an integrated, embodied sexual self is fundamental to a rich, full, authentic existence. So yes, this is now my field of work….I am a pleasure coach.

  21. Kristin
    Kristin says:

    Hi! I was just thinking about this! I am 29 and have a career in IT, but a few years back I was a copy editor. I heard about a job paying much more than I am making, but it’s an editing job. I guess it was interesting to think about it becoming the norm to switch back and forth between careers, since right now I am worried it will look really bad!

    • Sarah Wendtland
      Sarah Wendtland says:

      I am 41. Started out in computers, switched to marketing and then worked in both areas. Recently I completed a masters in Education. Don’t worry about if it will look bad. I’ve had a lot people comment about all the jobs I have held. I explain how all the experience gives me the know-how and a well-rounded perspective! It hasn’t hurt me, except that I can’t move into management. Do what makes you happy! That’s what I’ve been trying to figure out.

  22. poppygirl
    poppygirl says:

    as usual, relevant to the biz world, but not much else. Went back to science/research grad school and doubled my salary at 40. At 56, tripled it.

    Like the coaching piece, tho. Never hurts to get some insight/help.

    Photo looks like art, or that you need bifocals. Pink looks like a good color for you if that’s not too Midwest/San Diego…..

  23. Mom Doc
    Mom Doc says:

    Talk about making the wrong choice in my 20s… I am turning 35 this year, I owe almost a quarter of a million in medical school debt (none from undergrad btw,) two years out of residency, and all I want to do is stay home with my two children and homeschool them. Hanging out with them and providing for them to explore the world teaches me so much and makes me sooo happy. I feel so trapped.

  24. Havaladırma
    Havaladırma says:

    I was looking for DaMomma’s blog, which has moved, but she links to you, and wow, what a find. The stuff about how you (we) try to protect our things from the reality of life, just priceless (as is electricity).

  25. susan pagor
    susan pagor says:

    Hmmm I truly hope you are wrong that your earning peaks at age 35 just wondering what statistics you are speaking of? I am making more each year in my mid forties and must say my plan is to inch up yearly. I am far more focused in my forties about what I want and with my kids in school I can spend some solid time focusing on my career something that was not possible in my mid twenties and mid thirties as I had four young kids to care for. My point is every body has a slightly different situation and you really can’t say who is going to make what when.

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