reinventing yourself, and rambling thoughts on career change

April 30, 2014 |  Category:   life me rambling


I was presented with an interesting question on two separate occasions recently which really made me stop and think about my perception of myself. “What do you want?” In the context of jobs, deals or my career, it’s not exactly a question that I get asked since it’s usually about the needs of the client or the project. Usually it’s something along the lines of “what can you bring to the table? What can you do for this project?” But what do I want? It’s such a simple question, but a deceptively hard one to answer.


My particular issue has always been that I don’t really know what I want (well I kind of do in a big dream sort of way, but that involves some serious random luck with a lottery ticket. Yeah I know, happiness isn’t about money, but I wouldn’t object if it started there). While it’s been a painfully slow process, I’m finally getting closer to focusing in on what I want by identifying what I don’t want to do. More importantly, however, I’ve come to realize that I’m not allowing myself to acknowledge the things that I want because I don’t believe in myself enough.
Yeah. That’s a big one. It’s really easy to brush things off by saying, “oh, I’m not an artist, I’m not a writer, I don’t feel like an entrepreneur.” I do it all the time. I did it just an hour ago on a phone conversation I was having with a friend. I have no idea why it’s easier to discredit myself than it is to own up to my skills and accomplishments, but it is. It’s been pointed out enough times in articles that this can be a gender thing, that women aren’t confident enough, but I also keep having conversations with people about the difference between my generation (I guess that would be X) and the generations younger than us. I believe we might be the last generation to have this mentality that accomplishments and accolades are earned and the only way to get there is to work your way up and “pay your dues”. I’m certainly old enough to have earned confidence in my field, but it’s been hard for some reason to shake off the grips of perpetual self doubt. It gets even further complicated when you’re raising girls and trying to nurture their own self confidence. The irony at play here isn’t lost on me.
As you know, a career change has been on my mind for a long time (are you tired of hearing about it? Because sometimes I am). My own mom did it around this age, partially to leave a demanding physical job and partially because she didn’t know how she was going to send 2 kids to college on a nurse’s salary. It worked out really well for her and she tapped into a business side of herself that she never even knew existed. Even though I have a great role model in her, a career change is daunting for a lot of reasons. Logistically, the process of getting there can be challenging and time consuming and this is *after* you figure out what you want to do. But it’s also daunting because our identity is so tied to our jobs and careers (at least here in the US) and for me, personally, my sense of self worth is often tied to my ability to bring in a paycheck. We always get asked the question, “what do you do?”, so if we strip ourselves from our jobs, what’s left? A lot, obviously; we aren’t one dimensional, but sometimes it’s hard to see who we are without the filter of our careers.
This year feels different though. Entertaining a few recent opportunities has made me take a look at what I’ve done and what I can do. Not surprisingly, it’s more than I give myself credit for. It’s long overdue, but it’s time take ownership of what I’ve done with my career in the past so that I can define what I want in the future. It’s not validation from others that I need, it’s validation from myself. And if you’ve gone through a career change and reinvented yourself, I would love to hear your experiences too.

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  • Pink Ronnie April 30, 2014 at 7:22 pm

    Hello Jenna,
    I’ve been thinking about the whole reinvention thing too. I started my own graphic design business back in 2005. I loved it, and it helped to pay the bills while my husband went through college. A year and a half ago, I decided to close it down as it was no longer inspiring me. I knew I needed a change, and I sort of knew what I wanted to do, but I decided to just pause, focus on blogging (for fun) and let the idea brew. Eventually, my idea and my blogging sort of coincided and my friend Trish and I were able to start up a memory keeping and photography workshop here in Sydney. It’s been such a whirlwind, and so much fun. I’m so glad I stopped designing for commercial clients because if I hadn’t wiped the slate clean, I wouldn’t have gone into this different direction. Looking ahead into the future, I have all sorts of ideas and would love to see some of them happen. I think that’s the thing with the social media and the engagement that it brings – it’s opened up so many possibilities in terms of what we can do now. The key for me has been to keep asking myself: “What is true to me? And what can I bring that is unique and special?”
    Anyway, sorry for the ramble. I still love to come here and read your thoughts. Really appreciate this space of yours. Looking forward to sharing this journey with you.
    Ronnie xo

    • Jenna April 30, 2014 at 7:29 pm

      I always appreciate your comments Ronnie, and so glad to hear of this news. Yes, how do you transition from designing for clients to something else? It’s been a hard break for me, especially since jobs continue to come in with little effort on my part. Again, that the self worth and paycheck equation comes into play here. I like earning money and supporting my family. We need my paychecks, but I do think, unlike in the past, I’ve reached a point where I do feel like it’s the right time for change. Sometimes that in itself allows other opportunities to enter our lives. Good luck with your new endeavor!

      • Pink Ronnie April 30, 2014 at 8:05 pm

        I totally understand. I used to charge $100/hr and I miss that sometimes. But it’d gotten to the point where I’d become quite disenchanted with my work, and even when jobs came here, I would here myself whinging. I think that’s when I realised I needed to stop. Of course, Rick had started working full-time at that point so we no longer relied on my income to survive. Also, our family had gotten bigger and I’d been spending much less time on the business, so organically, it had already been winding down itself. Mmm… the transitioning. I forced myself to pause for some time and not actually rush into anything. I really wanted to make sure that what I did next was something I would love doing. It’s hard because you see everybody in the blogging world making leaps into this project and that project and it’s easy to catch yourself thinking ‘Oh my goodness I should be doing that and that’ or worse – thinking you want to do what everyone else is doing when really it’s not what you actually want to do at all. (Okay, that made more sense in my head.) I remember once you said “I like to write and I like to take pictures.” (Maybe not those exact words.) That would be an excellent place to start! Because, honestly, I think that you’re already a writer and already an artist. And a superb one at that.
        Ronnie xo
        p.s. Um, what time is it in NYC right now? :)

        • Jenna April 30, 2014 at 8:13 pm

          Thank you. I need to believe that myself and I am learning how to do that. Oh, and it’s only 8pm here. I have 6 more hours till my bedtime, ha!

  • Fiona April 30, 2014 at 11:20 pm

    Jenna, I did this about five years ago. I’m not in your field, though.

    I was on the faculty of a regional comprehensive university. I teach American history. It was a decent job and I loved my colleagues. But the teaching load was high ( a 4-4, four classes per semester) and the salary low. Plus, the thing I do the best – teaching – mattered least to the administration and to my success at the institution.

    So I went looking for a gig where I’d be happier. I now teach in a private high school. It’s a much better fit for me, plus more money and a lower student load (more classes, actually, but 2/3 of the students).

    For me, the trick was to identify the core of my attraction to the profession and alter my professional circumstances to reflect that new information.

    Thank you for continuing to blog. I find it very interesting and as my son ages I’m especially focused on your comments about parenting.

    • Jenna May 1, 2014 at 9:07 am

      Thanks for telling your story Fiona. It’s nice to hear that it all worked out for you – better pay and less workload, you can’t argue with that. For me…I do want to see if I can get out of my field completely, or is some capacity. I think that’s why it’s been so tough.

  • erin May 1, 2014 at 12:22 am

    Love reading about your career journey. I left publishing after 12 years doing sales there to take a job running a little retail store (really a bookstore) inside a gorgeous new library. It’s been the most insane learning curve: hiring and managing staff for the first time, becoming a retail buyer, planning events, both big and small, etc. No one says no to me but I have to learn everything from scratch on my own. It’s overwhelming and deeply rewarding. I know it’s not forever but it’s given me the chance to learn so many new things after thinking I only knew one field. And it’s also showing me that nothing has to be forever- that I can learn what I want to from this new experience and then take what I want to do next or what I now know I don’t want to do and move on to something else. It’s definitely helped me let go of fear of change. Anyway, that’s my rambling experience :)

    • Jenna May 1, 2014 at 9:08 am

      That’s great Erin. Yes, I do miss the learning that comes with a new career/ job. I think that this is crux of it, that I’m feeling stagnant right now. Thanks again for you comment.

  • Sam May 1, 2014 at 1:33 am

    I just turned 31 and have been grappling with this for the past 3 years. Still not sure what I really want – or can – do and with moving around am finding it hard to really commit to what I am doing 100%…
    I suppose at the end of the day if what you’re doing means you can live, makes you proud and is work worth doing then that’s all that’s important. But it’s finding out what that is for me that seems to be the problem!

    • Jenna May 1, 2014 at 9:10 am

      This is my problem too! Good luck, and I hope we both can figure it out.

  • Em May 1, 2014 at 5:25 am

    I used to do freelance webwork a few years ago, as I tired of it I wrote a list of things I wanted to try next – I mulled over the list for awhile and in the end crossed just one of them off the list – making online products. I started to try a few of the others, then I thought of a small online product idea that would take a couple weeks to get up online. I got it up, it showed promise. I kept tweaking things and a few years down the track, the one thing I crossed off the list is all I do and I’m having a great time. For me it was a series of small bets – some that worked out, some that didn’t. Still working a lot out but very much enjoying it. Good luck Jenna and look forward to reading about it here, thanks!

    • Jenna May 1, 2014 at 9:36 am

      Thanks for sharing your story Em – it’s encouraging and sounds like you’re having a great time on your new direction.

  • Lynn May 1, 2014 at 10:51 am


    I think we might be around the same age. I’ve been letterpress printing for 10 years now–and I’m ready for a change. I’ve been considering going back to school for a masters degree in public policy with a focus of social change. This is a huge shift away from studio life, but not such a leap when I think about what’s become really important to me over the years: issues of disability, accessibility, inclusion, and advocacy. I’m a year away from being able to start a graduate program (because, yikes, I’d have to take my GREs first, among other things) and so I’d be turning 40 the fall I start (if everything works out). It’s scary to consider such a change and yet I have felt less and less connected to the blog/design world and more and more sure that I need a different kind of challenge.

    I don’t really know if this is going to all work out, but I’m pretty certain I’m going to give it my best try. And I don’t think it means just walking away from the little studio business I’ve created either.

    xo lynn

    • Jenna May 1, 2014 at 12:58 pm

      lynn, totally can relate to wanting to disconnect a bit from the design/blog world. It sounds like you have a plan and a big change ahead of you! SO happy for you, but yes you’re right. This is the stuff that has been and will be important in your life so it makes so much sense. Good luck!

  • Lakshmi May 1, 2014 at 11:32 am

    It has been a very organic process for me and I believe it has not ended yet. Will it end? I don’t know.

    I began life (:)) as a civil engineering graduate (simply because I was in the Science stream and all smart kids went the engineering/medicine route, well most of them). I managed to graduate in four years, got a job in the software/IT field and started to work. I always knew that it wasn’t what I’d really like to do but I thought – hey, I have a job! I should thank my lucky stars, shut up and work. That went on for a few years and I became more and more aware that it wasn’t what I wished to do.

    Then come a stint at grad school, a MA degree in Mass Communication and a job in media/writing/communication. Yes, this is what feels most natural and meaningful and authentic to me.

    But is this my life path? No, it is a career and it may change, I know. I have dreams… :) Will see where life takes me. I have no kids, so maybe my options are different than others.

    • Jenna May 1, 2014 at 1:54 pm

      I think it’s great when we take meandering organic paths to get where we are. I’d like to think that we take a little bit from what we’ve learned at every job until we find the path that allows us to apply all of those skills and experiences. Sounds like you’re leaving yourself open and that’s great. I’m trying to do that as well.

  • Shelagh May 1, 2014 at 1:07 pm

    Hi Jenna,

    I’ve been a blog reader for a long time and may not have commented before.
    This post was so timely for me, it is exactly where my head is at these days!
    To be honest, this kind of questioning has been an ongoing theme for me
    and I envy those who KNOW what they want to do, what their “purpose” is.
    I, like you, have always had the grand dream of happiness and freedom
    but not necessarily a clue as to how I plan to get there or what my skills are.

    I am a new mom after 40 and I think that brings up a lot of these questions.
    I want to set an example for my son, to practice what I preach about
    being true to yourself, believing in yourself and working hard.

    I feel less like an outsider now that I’m a parent and even more so
    knowing there are talented, interesting people in blog land
    going through the same things.

    Your blog is wonderful and I’m rooting for you on your new path!


    • Jenna May 1, 2014 at 1:57 pm

      Shelagh, hello! Nice to hear from you. I know what you mean about envying those people who know exactly what they want to do in life. I think the only time I’ve felt that way was when I was younger in high school. It’s been a meandering path since then, always on the creative side of things, but always never a straight road. Congrats on motherhood! And thank you for your nice comment.

  • katrina May 1, 2014 at 7:56 pm

    It’s encouraging to me to read about other women who have changed directions in their lives, both in your original post and in these thoughtful comments. Sometimes I feel like I’m “too old” at 37 to consider a change, but then I shudder to think about spending the next few decades of my working life in this same capacity. I know what I want to do, but it is very competitive and very difficult to break into. I will keep trying but it can be a challenge to continue to try when I’m not having immediate, spontaneous success.

    And you mentioned this propensity you have to doubt yourself and your abilities. I do the same thing. I’m training to run my first full marathon, and I’m finding the biggest hurdles are all mental. I just don’t think I can do it. I have years of experience, a solid training plan, excellent health, but deep down I question if it’s something I am capable of doing. It’s enlightening to suddenly become aware of the fact that limitations aren’t always necessarily external.

    • Jenna May 2, 2014 at 9:26 am

      Oh lord, if you feel too old at 37, then how should I feel!? Truth is, it is NEVER too late to consider a change. Plus people are living longer/working longer/retiring later. I think it’s unrealistic to expect ourselves in one job or one career for the whole duration. I would get bored! I am bored! I would say you have a better start than I do because you know what you want to do. Good luck in your training…and yes, it is all mental.

  • Rachel May 2, 2014 at 11:44 am

    “…but I also keep having conversations with people about the difference between my generation (I guess that would be X) and the generations younger than us. I believe we might be the last generation to have this mentality that accomplishments and accolades are earned and the only way to get there is to work your way up and “pay your dues”.

    — A thought on this from a Generation Y-er/Millenial: I agree that the mentalities between the generations are very different, but something I’m a little worried about when it comes to myself and others having the mindset of instant, viral success or whatever you want to call it is that just because we have that mindset, that doesn’t make us right. Does that make sense? In other words, having the mindset of “Oh, I just have to get my stuff seen by the right people and then BAM, I’ll be an overnight success” is, I think, kind of delusional. We might not think we have to pay our dues, but we could very well be wrong about that. I think part of the problem is that we are exposed to so many final products or successful careers, usually online, and we don’t see the years of sweat and tears that it took to get to that point, so it looks like some kind of instantaneous process to us. But most of the time, that’s not the case. I think there is a lot of value to paying your dues, and I am seeing so much frustration in myself and others my age because we are in our twenties and not having tons of success yet – duh, it’s because we haven’t put in the time/effort yet, dummies. It’s also an issue of entitlement. Anyway. Just my rambly two cents. =]

    • Jenna May 4, 2014 at 8:47 am

      Thank you Rachel on your perspective. I think we are concerned (?) or talking about the same things. Sometimes I feel like we only hear the overnight success stories, but the reality is probably so far from that. Social media and the internet has a lot of play here, most likely, and it’s contributing to this illusion and perhaps affecting work ethic and job loyalty. People seem to change jobs so frequently these days. On the other side of this, I hear a lot of frustration from friends who are employers or the ones hiring.

  • Jennie May 3, 2014 at 10:55 pm

    I find it incredibly comforting to read your thoughts and entries about this topic. I’m a long-time reader, mostly because I love your writing and photographs and general sense of style, but also because I’m a designer with two young children and a baker husband (The Cheeseboard, across from Chez Panisse) :-) And believe it or not, I used to live about five doors away from Lighthouse Roasters up in Seattle.

    All that aside, a career change is something I’ve been thinking about for several years. I’ve had middle-of-the-night panic sweat attacks about it. I’ve wondered if I’m just the type of person who is always searching and never satisfied. I worry that I’m too much of a dreamer and not enough of a doer. Quite honestly, the biggest thing that holds me back is money. It’s hard to get past that, especially when I think about putting my two kids through college. But I know that way down the road, I’ll be extra pissed at myself if I realize I held back just because of money.

    There’s so much more to say because I think about this ALL the time. But it’s late and I’m starting to ramble. Please keep updating us. It’s inspiring and helpful.

    • Jenna May 4, 2014 at 8:50 am

      Hi Jennie! So many parallels to our lives (including the Lighthouse Roasters reference!) I hear you about middle of the night panic attacks. It’s true that some people might be the type to be constantly searching while some people can truly be happy with where they are in life. You can probably guess where I fit it :)
      Money is a big one, and of course that holds you back. Me too. I still have to earn a living so it’s hard to figure out when to do a career change when often it take a time and money investment to do so. Sometimes that feels a bit self indulgent when you have a family to support and kids to send to college–that’s been weighing heavily on my mind too, so you’re not alone there. Good luck on your search as well!

  • Melissa@Julia's Bookbag May 5, 2014 at 6:05 pm

    Ah Jenna. I went from being a lawyer, to a stay at home mom, to blogger, to…trying to be a photographer. It’s been ROUGH. Many a day I’d like to flee back to my law firm job, (which was low stress, strangely, and paid quite well), sit there quietly for 8 hrs and collect my paycheck. But I would see my daughter maybe 2 hrs a day. I just can’t call it quits on trying to make something work in a more creative endeavor, even though we have made great sacrifices in letting go of my paycheck. I feel like I got on the wrong road in the first place, with the law thing, and now here I am mid-life, trying to figure out what to be when I’m a grownup….

    • Jenna May 5, 2014 at 7:34 pm

      There’s a lot of us in the same situation Julia. I have to have faith that we will all figure it out, every one of us.

  • Shea May 5, 2014 at 10:45 pm

    Hi Jenna,

    I, too, have read your blog for a while. This is my first time commenting. Nice to meet you (sort of)!

    Just wanted to send some good wishes to you. I know there is only so much you can share in a public forum about your ideas and hopes, and all the whimsical things you’d do if you had a brilliant stroke of luck with a lottery ticket.
    I guess we will have to be patient and wait for the next phase to unfold.

    In the meantime, I hope you’ve got lots of coffee dates lined up with your most supportive, creative friends. A little caffeine-fueled imagination and conversation is always nice for bringing ideas into focus, even if they’re still around the bend.

    All the best,


    • Jenna May 7, 2014 at 5:10 pm

      Shea, thank you. And yes, I have been having more coffee dates with friends! Good conversations always happen during those.

  • Michelle May 7, 2014 at 5:07 pm

    At 40 I feel like I am in a similar situation as your mother, wondering how we will pay for college tuition for the kids. Also, feeling like Melissa above trying to figure out what I want to be when I grow up. I’ve been a stay at home mother for half of my life with my husband being the breadwinner. I came across this Denis Waitley quote that I found relevant: “It’s not what you are that holds you back, it’s what you think you are not.” I have faith, too that we will all figure it out. Everyone deserves to be fulfilled.

    • Jenna May 7, 2014 at 5:12 pm

      Michelle, I’m wondering how we’re going to pay for college too. It’s 8 years away. It’s weighing on my mind fr sure. I love that quote. It is so true!

  • Kristine June 12, 2014 at 9:58 am

    I just recently discovered your blog and I was instantly taken with your thoughtful, insightful writing. Very happy I found you. I am 45 and have been wanting to do a career change for ages. I am burnt out but seem to be stuck and unable to muster up the energy to move forward. I am still holding on to the hope that I will find my way, and I have no doubt that you will as well. Looking forward to reading about your journey.

  • Deena October 22, 2014 at 4:39 am

    Thank you for sharing this post, I’m so glad that I’m not the only one feeling like this, you’re all my kind of people *big hug, I also recently had the midnight panic attack I thought I’m about to lose my mind. Reading this post and all of your comments making me feel less alone because in real life not many people will not understand what we’re going through. I hope that we’ll be blessed with strength and love to unfold our beautiful journey ahead.