How to figure out what you should be doing with your life

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There is no other way to figure out where you belong than to make time to do it and give yourself space to fail, give yourself time to be lost. If you think you have to get it right the first time, you won’t have the space really to investigate, and you’ll convince yourself that something is right when it’s not. And then you’ll have a quarterlife crisis when you realize that you lied to yourself so you could feel stable instead of investigating. Here's how to avoid that outcome.

1. Take time to figure out what you love to do.

When I graduated from college, I was shocked to find out that I just spent 18 years getting an education and the only jobs offered to me sucked. Everything was some version of creating a new filing system for someone who is important.

Often bad situations bring on our most creative solutions. And this was one of those times: I asked myself, “What do I want to do most in the world, if I could do anything?” I decided it was to play volleyball, so I went to Los Angeles to figure out how to play on the professional beach circuit.

I spent my days on the courts, and late nights at the gym, and in between, I worked odd jobs in bookstores. And then I realized that the other thing I wanted to do was read. I had been so stifled in school being told what to read all the time. It was thrilling to be able to read whatever I wanted.

I wasn’t making very much money. Sometimes I couldn’t pay rent, and my landlord hated me. And sometimes I couldn’t afford to wash my clothes and I pretended that bikinis never get dirty. But, in fact, you really don’t need much money to figure out what you love to do, you just need time and space and a willingness to keep yourself busy until something sticks.

2. Take time to figure out what you can get paid for.

It took me a few years to navigate the arcane hierarchy of Southern California beach volleyball, but I finally played on the professional tour. For a summer. And what I found was that I am not nearly as competitive as the top players. I was, at one point, ranked 17, but I can tell you that I never cared as much about my rank as the other women.

What I did excel at, though, was winning sponsors, which, on some level, is what professional sports is all about anyway. I always had better sponsors even than women higher than me in the ranks, and I won partners and trainers by dint of my ability to attract sponsors.

But the truth about professional volleyball is that it is a really tough life. The eight hours a day on the beach starts getting old, and so do the Budweiser commercials I did (totally not fun) to manage to scrape together enough money to support myself.

So I thought to myself: Who is using the skills I have to make money? And I landed on marketing. And I had this boyfriend who was going to hire someone to do marketing at his Internet startup, so I volunteered to do it for free, to get something on my resume. And then I got a job.

3. Watch people around you to figure out who is happy.

I ended up having a pretty big job at a Fortune 500 company running their web site. Don’t get me wrong. It was the earliest days of the Internet, and it actually took more people to redesign my blog recently than it did to launch that Fortune 500 site in the early 90's.

But anyway, I started climbing the ladder and tons of people wanted to mentor me, to help me get to where they were. And they told me they were happy, but when I watched them, day in and day out, I realized that the people at the top of the ladder were not nearly as happy as I had expected them to be. They tucked their kids into bed from their phones at their desk. They were overdressed constantly and they had hair-trigger tempers for topics that seemed inconsequential to me.

So I went to where coolness seemed to be: At startups.

Now that I’m on my third startup, I can tell you with certainty that if you looked at my life you would not see that I am happy. Running a startup is really high risk and really difficult, and entrepreneurs work longer hours than anyone else. But I’m almost always there to eat diner with my kids, because I control my own hours.

So the final step of finding out where you should be is looking at everyone’s life with a clear lens. Adult life is really hard. Finding out who we are, and finding someone to share our life with, and having kids and still having a life, and being able to pay for all of that: Impossible, really.

So you look around and see who is doing what part of that well. And you pick the sacrifices that they made. Because no life is perfect, but all lives have some things to offer. Be clear on what you’re choosing and what you’re giving up, and don’t pick anyone’s life if they tell you they have everything: they’re lying.

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  1. malingerer
    malingerer says:

    this.. this was a good article.. needle in a haystack lately, but definitely better than those of late. thanks!

  2. Eric
    Eric says:

    So true. You have to make a “Priority List” and you cannot afford to put down “Work” when you are an Entrepreneur.

    Some friends can be bored to hear everytime the same excuse : “I can’t. I’m working. I’ll call you back, I swear.”

    Someone to share my life at this moment ? Too difficult.
    Have kid ? Oh, yeah. I want one from a long time. But I know that I couldn’t be a good father (nor a good husband) at this moment. My company is very young and I have a lot to do. I’m still young (27) and I keep “Work, Making Money, Have Fun” in this strict order.

    Until the time come when I’ll do enough money to hire someone to do a part of my work, I’ll keep this strict priority list active.

    Well, in fact that is full theory. I cannot stop myself to wonder “What if I make enough success with my first company to hire a top manager ?”. Maybe I’ll start another company. I’ve got plenty of ideas and that’s the trap. What if I’ll look back in time in few years and see only work ?
    I want a family. When ?

    That’s the “One million dollar” question.

    • laura
      laura says:

      Hope you do well with that whole “everything can wait until later” theory. My husband had that same attitude – wanted to get his master’s degree before we started a family, etc., though I REALLY didn’t want to wait. We had the nice big house and big yard and dog and all the rest. He died of a heart attack at 29, six weeks before his 30th birthday. Now I’m 40 and still haven’t figured out what to do with the rest of my life, since most of it centered around being a stay-at-home mom. Hated my job, still do, and I’ve never been able to afford to get out of it.

      Have fun while you’re young.

      • chelsea
        chelsea says:

        laura, that sounds like a very difficult thing to accept. i hope you do soon and live the life you deserve. you are loved and you are worthy. go and get it girl, go get that life you see in your dreams… or maybe you have to search a little to uncover what your dreams are… that’s okay to.

  3. Ed Borden
    Ed Borden says:

    Climbing the corporate ladder : Feeling frustrated all the time because you can never live up to your full potential, and depression comes from the fact that you can never set goals that allow you to do the best work of your life.

    Working in a start-up : Feeling frustrated all the time because, as a small fish in a big pond, outside forces are always able to affect your ability to succeed, with long stretches of time spent staring at yourself in the mirror wondering whether bringing yourself to the breaking point and keeping yourself there for prolonged periods is really worth it, or if being a corporate shill for the sake of your family really might be the sacrifice your one and half year old baby would choose if he was able to.

  4. Bethany
    Bethany says:

    With the review process at my “real” job starting and more and more of my time being devoted to “why can’t I do my volunteer work for a career?” this post was what I needed to read. Thank you, Penelope! Hopefully by this time next year I’ll have followed these steps to actually doing what I should be doing with my life.

    • mo
      mo says:

      Wow. hi im glad someone other than me has great heart too. please contact me lets talk. Maybe we can exchange ideas. N info.

  5. RedEye
    RedEye says:

    I normally hate those kinds of books, but I found the exercises in “Passion at Work” to be really helpful in sorting out my career issues.

  6. Jamie Varon
    Jamie Varon says:

    They were overdressed constantly and they had hair-trigger tempers for topics that seemed inconsequential to me.

    This seems to be one of the biggest indicators of general dissatisfaction. Sure, there are always going to be times where people need to vent, but someone who flies off the handle every time a small detail doesn’t go their way is a person that is battling their own unhappiness.

    I wrote an entry on my blog that fits into this topic. It was about how I don’t take everyone’s advice, because I have to screen who’s opinion matters to me. The URL to this entry is:

    I like your view on people. I like that you talk about who is really happy, versus who says they are happy. Too many times, we tend to take people at face value and not analyze their behavior to figure out who they really are. There are clues everywhere that can give us insight into people that go beyond what they choose to say and not say to us.

    Penelope, your insight and perspective is fantastic. Thank you for sharing.

    • Bethany
      Bethany says:

      HTML screwups happen. I’m impressed that you caught and addressed it so quickly. Penelope’s take on people is part of why I started reading her blog and taking the advice she offers. My version of happiness involves an emphasis on relationships, seeing all the ways Penelope lives that makes her advice easier to take–even when it’s hard or scary.

      Heading over to your blog on my next coffee break to read what you have to say.

      • Jamie Varon
        Jamie Varon says:

        Her advice is easy to take mostly because she’s so honest. She talks about her downfalls, even when she knows investors and anyone in between are absolutely going to read her blog.

        As an honest (to a fault) blogger, I know that it’s difficult to write something when you know people are going to read it and digest it in their own way.

        I’m heading over to YOUR blog right now, Bethany.

  7. KateNonymous
    KateNonymous says:

    Funny, I was just saying to Mr. Nonymous that I finally do have everything. Here’s the thing, though. It’s not everything. It’s everything I want. And I know what I want because I’ve lived long enough to think I know what I want, not get it, and be happy with something else–while observing other people who are happy and unhappy, and paying attention to what makes them so.

    Happiness is based on self-knowledge and priorities. It’s also based on choosing to be happy. Because just about everything can make you unhappy if you let it.

    • Dara
      Dara says:

      Kate, I think you hit the nail on the head. “It’s not everything, it’s everything you want.” I think the theme of a lot of Penelope’s blogs are really about taking the time to actually think about and/or try “what you really want.” That may not be a huge paycheck and high-profile career, but it might be. If you’re trying out your passions and always disgusted that you don’t have enough money, then maybe a career/work oriented life is for you.

      And I totally agree that a lot of being happy is choosing to be so. For me, it’s a religious, but also a great non-religious life philosophy: “Be content in all situations.” For example, as a young adult/teen (influenced by my well-meaning father who saw potential) I thought I wanted to be really professionally successful and make a lot of money. Fortunately, my passion for writing was so strong I tried to combine the two in a degree plan in college. I got off the career track really early voluntarily for my husband’s career/relocation. He’s the really well-educated successful, money-making one.

      I’ll never get the respect he gets automatically for his success. I guess I could envy that b/c I know I could have that if I’d chosen it, but I don’t. I guess I figured out that wasn’t what I really wanted. Instead I do what I love, make respectable but not great money and am envied for my flexible work schedule. Nobody’s going to say “Wow, you’re a (insert profession here)” to me, but I know very few people who are as happy as I am.

      • KateNonymous
        KateNonymous says:

        I do think that there are some situations with which one should never be happy or content.

        That said, I think happiness is often based in recognizing and appreciating the value of what you have. We just bought our first home. It’s small. I love it. If I wanted a big home, I wouldn’t be happy–but both of us wanted a small place.

        I’m not as passionate about my job as some bloggers would say I should be. But I enjoy it, I have great co-workers, and I get to go home on time the vast majority of days.

        Could I make more money? Quite possibly. But I don’t really need more money. We make enough to live the life we want, comfortably.

        My family is healthy and happy.

        There you have it. I’ve got what I want. And most of that is gravy, because what’s really essential to me is a happy and healthy family, and my husband in my life. If I didn’t have the house, money, or job, I’d still have those things. And if I didn’t have those things, what would the rest of it matter?
        But as it is, I have everything.

  8. Mark W.
    Mark W. says:

    This is a very honest post. I know about not settling and yet having had to settle for various things because adult life can be really hard and impossible at times. Life is a compromise no matter which way you slice it. It’s also a puzzle and a maze to navigate. Sometimes it’s fun and interesting and other times it stinks. I think controlling your hours to the extent that it’s possible is very important. I like your advice about looking at everyone’s life with a clear lens. Everyone would include ourselves. The last thing anyone of us wants to do is lie to ourselves.

  9. Oliver Bendzsa
    Oliver Bendzsa says:

    Thanks for the good think piece. Do you have any advice as to where/how to find the time to pursue good thinking?

    Aslo, this post reminded me of a Fast Company article from a few years back called, Balance is Bunk: “It’s the central myth of the modern workplace: With a few compromises, you can have it all. But it’s all wrong, and it’s making us crazy. Here’s how to have a life anyway.”


    • Lane
      Lane says:

      I LOVE that article in Fast Company (written by the owner of When I was a manager, I actually clipped that article out of my Fast Company and had it available to my employees. Sometimes, an expectation of “balance” is more overwhelming than just doing what you can, when you can. If you have this sense of “I should be feeling this way, but I don’t” you can stress yourself out.

  10. Susan
    Susan says:

    “Everything was some version of creating a new filing system for someone who is important.”

    That’s really well said. I could never put my finger on why the early stages of my career felt kind of hollow. I never felt like I was contributing to -something- important, just to make someone’s (who was more important in the office) life easier.

    I became a writer instead.

  11. Ian
    Ian says:

    “And then you’ll have a quarterlife crisis when you realize that you lied to yourself so you could feel stable instead of investigating.”

    So what if I’m already at this outcome? Now what?

    Anyway, really digging your blog and I really like this post. So much more grounded than the “if you can dream it, you can do it!” BS that so many others who weigh in on this topic seem to fall back on.

  12. Tiffany
    Tiffany says:

    When I decided that I wanted to be a hotel manager many people told me that it wasn’t the right career move because of the hours and lack of free time. Many of the successful people in this career told me the same thing but it was one sacrifice that they never regretted or felt was a sacrifice at all. Like them (or not) I have a partner who is willing to be as flexible as I am and who is down for the adventures that that career choice could bring. I questioned my choice a few times because I would like to be as much around my child as possible. But just like he has to live and discover his calling, I have to as well. I had to remember that even while being a mom, it was ultimately my life and my choice.
    Great post, as usual!

  13. Natalie
    Natalie says:

    Really appreciated that one. Great advice – food for thought and the encouragement I needed to keep mulling over my options – with a bit of structured guidance thrown in for good measure.

  14. KerrySS
    KerrySS says:

    You know, lately I’ve talked to a lot of people who are “trying to figure out what to do with their lives.” I don’t get that. Is there only ONE thing you should be doing? Is it a lifetime commitment? Doesn’t the “right thing” change over time?

    I did the thing that was right for me in my early and mid-20s. Then, the “right thing for me” changed, and I did that for a decade or so. Then the “right thing for me” changed again, so now I’m doing something else. When it changes again, I’ll change too.

    People act like this is some big thing you have to figure out. For some people, I guess it is, if you are really set on being something that requires a linear progression. Fewer and fewer things, though, require a linear progression.

    I can see why it seems like such a big question if you treat it like a lifetime commitment…but it isn’t. It’s more like a hairstyle. You wear what suits you until it stops suiting you, and then you change it. The happiest people I know are the ones who get that.

    • thatgirlinnewyork
      thatgirlinnewyork says:

      i agree very much with the sentiment that one’s career at any point should be a “lifetime commitment”. I’ve tried to live that axiom, and it’s been successful and not-so at the same time. but we also live in a society that for too long expected you to live for one career, because it’s easier on HR directors and recruiters who DON’T support transitions or changes, let alone understand them. most people would be happy if they could easily change their direction (and do so without having to worry about debt, healthcare coverage, and all the other very un-sexy needs in life).

  15. mamaworker
    mamaworker says:

    I am turning 30 this year and I think I’m still having my quarterlife crisis, so I appreciate the reference! I too was shocked entering the working world – mundane. Right now my family is more important than work, but seeing as I still have to work, I’m looking at expanding my skills set to shake things up. Thanks for a good post.

  16. Sam
    Sam says:

    I’m still considering what I want to do. I should really spend more time thinking about it as it is very important. It is just too easy to put things off.

  17. Milena Thomas
    Milena Thomas says:

    I love that you talk about not having it all. I hate that that concept has been forced upon us via annoying, overly-happy, pop-psych pushers.

    Uh, I guess you can see I’m a little bitter.

    But I’ve found what makes me happy for now: being a wife, and being in grad school. Anything else that happens beyond that is icing.

    I know my needs will change – and that will likely mean giving up something else, because we can’t have it all.

    Like, I could really use a marble bathtub…

  18. Problemsolverblog
    Problemsolverblog says:

    I call jobs that you do in your twenties “figuring out what you DON’T want to do.” I ended up with a nice long list, went and got my Master’s degree in something I did want and then was off and running. (Actually, getting kids and married and a home wasn’t all that much of a breeze, but at least I had a list of jobs I hated.)

  19. Grace
    Grace says:

    Lovely post, but Penelope, are you really happy?

    Your honest blogs are filled with strife, tension, fatigue, and tears. Sometimes, we think our work sacrifice is worth it because it will only be for a while -we think things will settle down when the start-up is started up. But it only gets crazier. Are your truly satisfied, not because you know you worked like a dog all day in an important job, but because you did something you truly received enjoyment from?

    If we are to look to someone that is truly happy in their work for inspiration, I think you inspire me to want to slow my life down even more.

    Just as a previous post debated the difference between nice and kind, perhaps we should debate the difference between happy and content.

  20. Dale
    Dale says:

    Corporation: Stifling, working for someone else
    Startup: Risky, scary

    How about starting a business while you’re working in the corporate world? You use your job as a venture capitalist… granted things probably go slower because you don’t spend as much time on it, but you reduce your risk a ton.

  21. Fox
    Fox says:

    I am in a good place but without anywhere to go. I work really hard and get accolades and recognition, but noone has offered to mentor me. I have only been with my company for nearly 2 years, but I’m impatient and unhappy. I haven’t found any other jobs out there – especially in this crappy economy – I can’t go out on my own. So I’m stuck. This is the longest quarterlife crisis ever…

  22. Marsha Keeffer
    Marsha Keeffer says:

    This is a tough post….finding what you want to do can be frightening – especially when you’re in that search state. And the truth probably is that there are several (even many) things that we’ll all do. I like thinking that if one thing doesn’t work out, there are many other opportunities for me.

  23. Karen
    Karen says:

    It is so scary to have HAD a long, successful career(by the traditional standards of money and title that I never even tried to question). And to now be looking at what to do next because your job is gone, and what you had been doing is no longer an option.

    Quite honestly, I have been STUCK. For quite a while. I have been going round and round without really asking myself what I love to do, or giving myself permission to try it. I have decided (as of reading this post – this morning)to spend at least one hour per day for the next month — until Valentine’s Day — to work on this and take some scary steps. They won’t all work. And one month will just get me (hopefully) moving and thinking. People in my life won’t necessarily agree with me or even support me. But I’m ready to do this for me. Penelope, thank you for the push!

    • Kathy
      Kathy says:

      Karen, you post said it all for me. I’m trying to determine that next step, that right move that will make the discomfort of the last years all just part of the process. But I’m finding it really tough to break free of old patterns, regain my confidence and strike out in a direction that will bring me back to me. I think it will happen-most days! In the meantime checkin’ in with Penolope’s reminds me I’m not alone and I like her emotionally honesty.

  24. le
    le says:

    We have a lovely speaker here downunder – a honest and interesting woman named Terry Hawkins … she says to be happy do happy … I totally get this. It’s about choice and choosing your response – being responsible for oneself. One of Steven Covey’s lines too I think.

    Not always so easy as we love to blame the boss, the weather, our mothers and our partners …

    So do happy folks and live your life your way – cheers le

  25. Kathy Caprino
    Kathy Caprino says:

    Thanks, Penelope, for your great straight talk and tips. They’re very “real.” As a career coach for people in transition, I recently blogged about “a job” vs. “a calling” ( I think it’s critical to figure out which one you have, and which one you want. They’re very different, with benefits and costs to each. In the end, we don’t reinvent ourselves and our work overnight, but with an empowered perspective, letting go of the behaviors and beliefs that keep you stuck, and saying Yes! to what compels you, it can be done! Thanks for sharing your fresh perspectives. Best, K

  26. Jason Zimmerman
    Jason Zimmerman says:

    There are some new web sites that I recently discovered that are geared towards helping people with career and jobs that I just talked about on my video show The Web Mix.

    There is one site that is brand new that helps with your career path and there is another one that is aimed at college students to help them get their resume online.

    I think there is a lot of value in this episode for job seekers.

    Take Care,

  27. Elizabeth
    Elizabeth says:

    I love this blog entry! I’ve been feeling very unhappy in my current career and I want to pursue something that I will enjoy waking up and going to. Yet, whenever I talk to someone about this topic I always hear “it’s not realistic to think that way” or “its impossible to find a job you absolutely love.” This entry gave me some hope that there truly is a position out there that will give me the fulfillment in my work life that I’m looking for. Thanks!

  28. GenerationXpert
    GenerationXpert says:

    Something that helped me be happy was to just stop bitching and make an effort to enjoy some stuff. It took me a long time, but I can roll much better with the punches now. I still get disappointed when work stuff doesn’t go my way, but being able to just have some fun has made a difference.

    This year my New Years resolution was to go out more. And it’s made me happier. I used to have big New Year’s resolutions (usually career related). But now I make an effort to just enjoy the life I have. Live in the moment. Want what you have and you’ll get what you want.

  29. sophie
    sophie says:

    I smile to myself when I think of “figuring out what to do with your life.” I’m almost 50 and from the time I was 19, quit college and got married because I was pregnant, my life has been full of surprises. It’s never gone in the direction I’ve planned. As a result, I gave up trying long ago and now take the paths as they come.

    That’s not to say I live recklessly or never make decisions. Of course not. Check lists, annual goals and business plans are a fun relaxation for me. But when I fail to accomplish a weekly to-do list because my child had an important school event, it doesn’t matter. As a spiritual person, I’ve learned God has the overall plan for my life. I’ve also learned it’s a good plan and I’m very happy with it.

  30. Ben Stroup
    Ben Stroup says:

    I’m always amazed at how many people – if given the opportunity – would want to do something else, even if they aren’t sure what that “something” might be. Just finished a great book on vocation, The Echo Within, by Robert Benson.

    Discovering what it is that we are meant to do and want to do and need to do is hard work. Growing up, everyone made it sound easy. But if it’s so easy to figure out, why do so many feel “stuck” in life.

    Thanks for drawing attention and adding to the conversation on a subject that can be overwhelming and scary.

  31. Brian Kurth
    Brian Kurth says:

    Spot on, Penelope, regarding your comments about a start-up being the most difficult thing to do — ever. I so see stories about someone with a great idea and they have a successful, money-making business in a year. Well, that DOES happen. But the reality is that most of us entrepreneurs work our asses off and put ourselves, spouses, family and friends through a roller-coaster of highs, lows and economic instability for a minimum of three years….and often much longer than that. I speak from experience on that one. Not sure where I’d be if it weren’t for my partner, Wade, my family and friends cheering me on along the entrepreneurial path.

    When I hit the three year mark with VocationVacations in 2007, I wondered, “OK, where are the big bucks? I hit three years. Isn’t it suppose to happen now?” The truth is it takes much longer for most of us. Especially if you’re starting a business from scratch versus purchasing a franchise business. I love the story of the folks at Stonyfield Farm yogurt. It took them something like NINE years and over 250 friends and family investors to become profitable. Sometimes, that’s what it takes. But they did it! All due to unwavering passion, fortitude, determination and, at times, throwing all caution to the wind with the faith that it’d work out. It did.

    I write this comment from my sunny but very small “corner office” of VocationVacations’ “world headquarters” (all 400 square feet of it!) here in Portland, Oregon. Views of a stunning Mt. Hood this morning. I came in at my own time after not having to commute as I once did in my 12-year corporate life in Chicago. In fact, I now even hit the gym in the morning. At nearly 43 I’m in better shape now than I was at 33. And, although I still put myself through the fear of the unknown and lack of economic stability that comes with a start-up versus a “secure” corporate job (but, as we’ve seen, they’re really not always so secure, after all), I won’t trade in my flexibility, autonomy and creative work for anything in the world. I may not have “the corporate corner office” but I sure do have a corner office that works just fine for me. And I really encourage others to do the same. It won’t be easy but if you have any sense of being an entrepreneur, now’s the time to go for it. What do you have to lose other than some time and money? Nothing.

    Brian Kurth
    Career Coach, Founder of VocationVacations & Author of Test-Drive Your Dream Job: A Step-By-Step Guide To Finding And Creating The Work You Love (Hachette, 2008)

  32. Grace Briones
    Grace Briones says:

    I really loved this article, Penelope. I’ve been reading your blog for nearly 4 years now. This is your best post yet. Your advice helped me through my quarter life crisis back when I was 25, with big dreams of becoming a CEO, admiring the likes of Marissa Mayer. I’m turning 30 this year. I ‘m married with a 16 month old daughter and a fairly toned dowm career that allows me to get home no later than 5:30pm. You’ve consistently been right about one thing: Relationships make you happy; not career success or money. I took a leap of faith sometime in my late mid-twenties and took this advice – it was scary at first to scale back on my career ambitions. But, what I got instead, I wouldn’t trade anything in the world for. I invested a good amount of time just hanging out with my then boyfriend (now my husband) and truly getting to know myself. I don’t have everything – BMW or the million dollar loft downtown. But I think I have the things that matter; the things that can sustain a fairly healthy, most times happy, well adjusted life: family and friends. Invest time in family in friends. Cheers.

  33. says:

    Reassurance. Penelope, that's what you have given me. After spending the past 15 years in PR and Communications, I've decided to take a year off and find a trail that leads to my passion. My goal has been to inhale and absorb as much knowledge of what's out there as well as understanding my purpose. As crazy and risky this move has been, I have had the good fortune of having the support of my family and friends. Reading your article has strengthen that support even more. Thanks for your validation.

  34. principalspage
    principalspage says:

    My advice to students as we send them off into the world… find something you love and are passionate about… something you would literally do for free… then find someone to pay you for it.

    And most importantly, realize your thoughts, ideas, and standards will change over time… so anticipate your occupation also changing.

    It’s advice that has been around forever, but I think it still holds true.

  35. Anca
    Anca says:

    Great post. I think I ought to come back and reread it once a week. I’m trying to figure out what I want to do with my life and how to get there without getting sidetracked into another uninspiring job, but I feel like I’m doing it with my eyes closed and I don’t know how to open them. (This economy is certainly not helping matters.)

  36. Froggylou2
    Froggylou2 says:

    This article definitely speaks to my heart. I love that I’m not stuck in life, and that I have the guts to do what I want. People always tell me that I’m so busy with volunteering, working two jobs, etc. What they are missing out on is that I’m busy getting experience in the places I want to be. When a spot opens at the company I really want to work for, I’ll already have the experience and still managed to pay my bills.

    I think it’s crap when I ask people what they would really like to be doing and they respond “this or that BUT I have bills so I can’t pursue it.” Load of crap! Everyone is in charge of their own destiny and if you want to do something- make the time to do it. The best things are sometimes the most difficult to achieve.

  37. jenx67
    jenx67 says:

    Great post, and great comments. I wonder if those who commented about their disenchantment in the workplace are Gen Xers working for Boomers. A $5 Starbucks card says every single one of them is an Xer.

  38. Karl Staib - Work Happy Now
    Karl Staib - Work Happy Now says:

    I’ve been watching more great people who are around me from great bloggers to co-workers at work. All I’m doing is taking notes. I’ve learned a lot from you, Penelope. The openness and easy to read writing style has become a part of me. I’m not quite as open with my sex life, but you are one of a kind.

    The most important thing that I have to add is trying all these things. Not just reading, learning and listening, but actually trying and failing is the most important part to doing what you love. When you fail you figure out how to use that to your advantage and make sure that pain never happens again.

  39. Reality Check
    Reality Check says:

    This makes 2 mostly reasonable posts from Penny in a row.

    In my experience, the only place to be is in small business. In really large firms, moving up is obviously who you know, how many asses are you willing to kiss, and how much kool-aid are you willing to drink. If you are in one of these and feel alone, rest assured the person 3 levels above you has to get up everyday and kiss dirty asses all day just like you do. It doesn’t change until you are at the very top — and these people will do everything in their power to keep others from getting in.

    Yes, small business is hard and being an entrepenuer is hard, but at the end of the day, you can work without losing any self-respect. That is, of course, if you have a real business with real products and real customers. It’s still difficult, but you are choosing your own path and making as much money as you like.

  40. Steve Errey - The Confidence Guy
    Steve Errey - The Confidence Guy says:

    Too true Penelope – allowing yourself the time and space to evolve and roll with things is one of the very best things anyone can do, and I think it takes a good deal of courage too.

    Pressurising yourself to have all the answers right now just doesn’t work.

    Adding to point 3 – Watch people around you to figure out who is happy – I’d add that you watch yourself to figure out what makes you happy. What are the things that feel good, where have you felt like you’re firing on cylinders and doing great work? Where have you felt most like you?

    My life and my career continue to evolve, and while I’m looking to make changes this year I know that difference between getting everything I want and honouring what’s most important to me.

  41. Dan Erwin
    Dan Erwin says:

    Penelope: Great post. Esp, “if they tell you they’ve got everything: they’re lying.” For me, I looked and moved gradually into what I liked, always recognizing that there would be a few things I didn’t like about it. So, first career–11 years, second career–11 years, third career–25 years, fourth career–just starting. Uhhh, don’t add those up. My rule: Never Retire. (I’t the most asinine thing on the earth.)

    Oh yeah, just as you, each career builds upon interests and expertise from the previous career(s). That’s the nature of career development–evolution far more than revolution.

    And another thing I’ve learned: developed friends in other industries/vocations–and develop friends in other generations. E.g. I have nearly 20 close Gen Y friends, two of whom are intimates. Not only does that spice up my life, but it also gives me both different lens and different perspectives.

  42. Lise, Melbourne, Australia
    Lise, Melbourne, Australia says:

    Loved this post in as much as it was so pertinent to me but in that it spurred a thought that isn’t it wonderful that we live in a time where people are actually questioning what they do, whereas even when I left school in the late 70s and the ultimate question ‘well what do you want to do when you leave school’ hits you full face and obviously you HAVE to DO something, anything which is what I did. Have no regrets that I didn’t become that surgeon I longed to be, but the fact we are all thinking about how we like to spend our time and make money from it is liberating, obvious but true. Its not so long ago that we lay back and thought of England as far as our careers ago and as a woman years before that our only option was to be the happy wife and mother, our best and unpaid job! Questions are good and finding the answers fun. Imagine how the world will look in even 5 years with people endeavouring to make their lives happier through finding work they love!! Your post has given me fodder for my moleskine, thanks Penelope! Love ya, Lise:^)

  43. Melissa
    Melissa says:

    Last week I finally sorted out my office and settled in. The funny thing is that I’ve been here for 9 months. When I came here I was taking the promotion for the money and planning on getting out of here as soon as I could make it on my own somehow.

    Slowly I began to realize all of the wonderful things this job has given me. Easy hours, great co-workers, the occasional sense of accomplishment, a level of autonomy, a really great paycheck (this is a big one) and I am able to be home by 5:30 to be mommy. Would a life of self-employment give me all of these things? Would I be able to walk away from my business at 5:30 and put on my mommy hat? Would I go to sleep at night secure in the knowledge that a paycheck was forthcoming every other week? Probably not in the early stages.

    So I have decided to stay. It’s not the ideal job, but it has so many great aspects and I finally realize that you cannot have everything you want, but there is much that you can have if you are willing to be flexible.

  44. John
    John says:

    What was the Fortune 500 company, Penelle? I don’t think one of them had a web site in the EARLY 90s!!

    You are so fulluvit.

  45. Danielle
    Danielle says:

    This was a great read. I am inspired to continue pursuing what it is that I love to do….reading, writing, and music. Even though it doesn’t make me ANY money :)

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