when being your own boss isn’t enough

April 27, 2011 |  Category:   life me rambling

I’ve been feeling restless again. Oh, you know me…it’s nothing new, but I’m feeling like I need to do SOMETHING. A change – and I will be the first one to admit that this feeling is cyclical – but here it is again, for the umpteenth time. I have lost count. That feeling. Perhaps I am fickle. Or bored. Or unchallenged. Or restless.

I know I declared this very thing almost 2 years ago. That I wanted to make the moves to transition careers, but then….I had the best year ever as a freelancer, after having my best years as a freelancer the 2 years before and I was busy, no room to even breathe. The surprising thing about it was that I actually felt fine being a designer. I didn’t hate it or make excuses about hating it as I have so often done in the past, plus we weren’t struggling financially like we were before. It was nice to have money and be able to take a yearly vacation and to buy not only things we needed, but wanted. Ironically, we flourished during this recession and built something from nothing in the process.

But, it doesn’t feel like enough.

There is still so much work to do if we want to grow our brand, but I have yet to figure out how my skill sets fit into this puzzle on a daily basis long term. It may not be enough. I want to do more.

Sometimes it’s really difficult when you are your own boss and you work independently to feel any real quantitative measures of success when you’re not on that corporate ladder climb. There isn’t anyone to give you a raise. There aren’t promotions with job titles. There aren’t co-workers or staff or a boss telling you that you did a good job. Those affirmations that are traditionally built in within a corporate structure don’t really exist in the freelance world. When you’re the boss, all of this is on you. Often, you feel like you’re just moving laterally and not up. And so, this is what I’ve been feeling. That despite the fact that I’ve worked on some pretty interesting and high proile projects, I feel like I’ve been moving laterally for the last 10 years, but not really going anywhere professionally.

There was an interesting thread on my NYU grad school listserve about a month ago. Someone had posted their frustrations during a job search because of the ambiguity and changing nature of the jobs in their field. They wanted to shift to something related but still within that discipline, but was having a hard time defining that role to possible employers. Someone replied back that it wasn’t until she started calling herself that role and thinking of herself in that role that other people started seeing her that way too. I think that’s really good advice.

So friends, an answer to a question has finally emerged that has been so elusive to me in the past. “What do you enjoy doing? What do you feel passionate about?”. It may not be the one and only thing, but for now, I can stand by this answer and believe it to be true, and it’s that I like taking photographs and I like telling stories. Let’s see where this goes.

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  • gia April 27, 2011 at 6:06 pm

    Good for you for speaking up about it. When I start freaking out about my priorities and how to change paths, I journal about it and it helps immensely. It also helps to talk to my recent MBA graduate brother who looks at it without emotion.

  • Wendy April 27, 2011 at 6:18 pm

    God, how I can relate to this post! I think that is why I feel validated with my press pieces as we had briefly touched upon via Twitter. Your photographs are beautiful and I think you are on the right path.

  • Susan April 27, 2011 at 6:43 pm

    I so relate…I have gotten “that feeling” throughout my life, wanting more-whether it’s more of a challenge, more excitement, more knowledge. I’ve never truly put my finger on it. I started my own design company in 2006, and it is still going (although having taken on other forms). I enjoy making a beautiful home for myself and others, I know that for sure. But lately that doesn’t seem like enough for me…the blog helps, but I’m still searching, like you. 😉

  • Bess | English Muffin Shop April 27, 2011 at 7:05 pm

    Your stories and photos are the very reasons I love your blog soooo much! They are honest and real and beautiful in their simplicity. I think you’re definitely on to something and naming that thing just makes it even more real. Go Jenna!

  • Pirco April 27, 2011 at 7:18 pm

    there ARE similarities in the freelance world…
    instead of your boss giving you a raise, you just raise your own rate (I just did this year :).
    instead of a boss or co-worker giving you praise, your clients tell you that you did a good job (at least, they should).
    just remember how lucky you are to be able to make your (next) hobby into a profession. I know you’re good at it, though!

  • Jenna April 27, 2011 at 7:21 pm

    Alright @P, I knew there would be someone who would chime in with that. Of course this is all true, but you know what I mean!!

  • Kelsey April 27, 2011 at 8:36 pm

    What that person said on the NYU forum is exactly right. Speaking as someone who is graduating college in a month and a half and is starting to job hunt, I found that when I stopped saying, “I’m a web design student”, and started saying, “I’m a web designer”, was when I finally *felt* like a web designer, and when freelance clients started taking me more seriously as such. I stopped referring to class projects in my portfolio as such and simply called them “projects”…I stopped talking about classes/teachers when I met with prospective clients…and suddenly *bam* I’m one of those “real” web designers too.

    It is so true, and such good advice.

  • sarah April 27, 2011 at 9:57 pm

    I know exactly how you feel in so many ways Jenna. I think it’s pretty amazing that you may have found a new thing in photography. You’re certainly great at it & always inspire me to take more photos of everyday goodness. I’m trying to figure out my next thing as I too am crazy bored with what’s going on right now. I lack that adventurous free spirit that so many small business owners have to just dive right in… so instead I stay at a job I hate (though there isn’t really anything wrong with it) and struggle to turn my side work into a career. Perhaps one day I’ll stop analyzing every “what if” and just go for it!
    Your personal stories are always so inspiring… thanks for being so open on your blog. 🙂

  • jennifer April 27, 2011 at 10:44 pm

    Yes, yes, YES!

  • Kath April 27, 2011 at 11:06 pm

    I adore your photographs, and I adore your stories. Do it!

  • Sandy April 27, 2011 at 11:23 pm

    Your blog and photos are amazing. I love reading your stories. You can do it!

  • lesley April 27, 2011 at 11:39 pm

    echoing all the sentiments above! jenna, i love visiting your blog because the way you tell stories makes it feel like we’re just hanging around shooting the sh*t. it’s familiar, easy, and comfortable. you have a wonderful way of painting a picture with words, and your awesome photos just top that off perfectly. whatever you’re on to, it’s going to be great. have fun and enjoy the first step, the revelation!

  • Renita April 27, 2011 at 11:54 pm

    And you are damn good at photos & stories

  • shruthi April 28, 2011 at 1:35 am

    my whole career and life has changed based on the premise of passion and the last paragraph in ur post!!! I AM the last line that you wrote. anyway, I am passing on the Versatile Blogger award to you, which is a blogger to blogger award. As much as this sounds like a chain, its a good way to route some extra traffic towards blogs that deserve them and showcase some extraordinary talent. You are one of my picks simply for your honesty and thoughtfulness and it helps that you and Mark run whimsy and spice!

  • shruthi April 28, 2011 at 1:37 am

    Oh shoot u can read about it here – http://photoppurtunist.wordpress.com/2011/04/28/versatile-blogger-award/

  • gizella April 28, 2011 at 1:39 am

    YES! do it! love your pix, your stories,go with your gut

  • heidi leon April 28, 2011 at 5:18 am

    Jenna, you have a strong firm voice that can easily connect to people. Your photography is honest, real and able to express so many tones and emotions.

    You really have a talent writing and photographing life, and maybe you can find a way to add your design skills and knowledge to create art.

    Perhaps a sweet fine day photodocumentary book?

  • Jess (Where My Heart Is) April 28, 2011 at 5:50 am

    Jenna your photos and stories have me captivated… so I think you are on to something.

    I put my career on the back burner 19 years ago when I had my daughters and until recently I felt it was enough. It really did fulfill me. If I had to do it again, would I do the same??? Not sure. I am advising my daughters to keep their finger in their careers/passions once they start a family (at least part-time) as it helps validated who we are. Maybe if I had had a career that was my passion I would have not given it away!
    Be true to your heart.

  • Stéphanie April 28, 2011 at 9:55 am

    Another question that is so difficult is that when you make a choice, when you engage you in a way, when you open a door,you close other ones especially when you get older. Sometimes it’s like you need two, three or four lifes to know what you are made for or what is good for you and furthermore, it’s not always the same at different ages.

  • Annie From Seattle April 28, 2011 at 9:57 am

    Yes. Do it!

  • Caroline April 28, 2011 at 10:32 am

    Oh this I can relate to! For good, or bad..
    I think the creative person in you craves change and needs to evolve. Its a sense that doesnt really go away. Being creative, however you do it, is a way to explore and make sense of the world, make meaning. I find design taps into my creativity but doesn’t allow me to create anything meaningful to *me*. When I make art, it does. I think it’s because I’m actively reflecting on my day to day observations when i make art (it’s almost diaristic) but I don’t get to do this kind of reflection in my work as a designer. I wonder if this is what you’re going through?

  • heather April 28, 2011 at 12:04 pm

    I can completely relate. I have practiced an art form for 15 years, spent a ton of money on graduate school (still paying off debt), built a community of friends and peers around this art, and now find myself increasingly disconnected from it and unmotivated to practice it. It’s an awful feeling to admit to yourself that you’ve lost the passion for something you have long identified yourself as (still identify yourself as); that you’ve invested so much in, and that you know you’re good at. What do I do now? I have skills, sure, I live in NYC where there are opportunities in many fields, but how do I transition my skills to something else, how do I find that next thing I can be passionate about, and most importantly, how do I go easy on myself during the transition? I can’t help but think I’m a ‘failure’ or ‘giving up’ – these are words that tend to be applied to artists when they transition to something else. Or maybe they’re not – it’s just the story I’m telling myself.

    In my experience, renewing yourself in your late 30’s/early 40’s isn’t filled with excitement – it’s filled with panic, disappointment, and even some (wrong, I know!) regret.

  • Vanessa Rae April 28, 2011 at 12:10 pm

    I enjoy the way you capture your life through words and photographs. It’s easy to compare yourself and feel like a little speck in the creative spectrum but I think if you determine what you consider happiness and success then there is no glass roof when it comes to a creative life. Just keep doing you…

  • heather April 28, 2011 at 12:13 pm

    btw – my situation is clearly different from yours – I didn’t mean to imply it was similar (“I can relate…”). I think I’m where you were 2 years ago. Either way, I’m encouraged by both your realization of what it is you want to do, and your commitment to pursuing it. Your photos are so personal and your stories relatable. Look forward to what’s next.

  • Loren April 28, 2011 at 3:16 pm

    I am finding it less typical for people to remain in the same job their whole lives as my parents and countless others have in the past and instead become “restless” or grow and seek out new occupations. I don’t think it is something to ever be apologetic for, either. I have only been out of undergrad for five years now and am already finding myself straying from the world of illustration and design that I had worked so diligently toward since I was old enough to contemplate college. Sometimes you spend so much time hoping and picturing life a certain way that you are shocked when you realize it is not what you planned and perhaps not the correct fit after all. I realized I wanted to be busy and enjoy my job but have flexibility and enjoy life out of my job as well. That decision actually kept me from pursuing further freelance art endeavors and sent me into a world of education and children. I couldn’t be happier and am now regaining my love for art that I had lost when it became a chore.

  • Catherine April 28, 2011 at 4:36 pm

    I think life is meant to be enjoyed and savored. That’s one reason I have always struggled with working. I know many people find immense pleasure in their jobs, but for me the pressure itself of work is debilitating. It doesn’t help that I have an illness that feeds on these feelings. I am lucky enough to not have to work unless I want to, this brings amazing freedom. I find myself dabbling here and there in different creative pursuits and slowly but surely, I am learning to enjoy a simple and fulfilling life.

  • Justine April 28, 2011 at 5:04 pm

    Do you really, really, really never want to monetize this blog. I know you don’t, but I bring it up just one more time because you ARE a blogger. Yes, you’re a designer and a small business owner. But you are also a blogger. And I for one think you are good enough to get paid for your talents (if you want to).

    Just the other day someone asked me what I did. For the first time ever, I said, “I’m a blogger.” “Really!” They said. “I’ve never met a blogger.” “Really!” I thought. “Doesn’t everyone blog?!” But actually it felt good. I felt like, “Yes, blogging is really an end, not just a means to an end.” And I enjoy it, so why not.

  • Jenna April 28, 2011 at 5:17 pm

    Nope, I don’t. I already did the blog/ad thing and I have zero interest in it. Blog advertising isn’t like it was back in those days so the money I’d make on this blog wouldn’t be much anyway.
    The ONLY way I’d consider it is if this blog grew so much in traffic that it would cost substantially more money to host this site, then yes, I might ONLY to offset hosting costs.

  • Justine April 28, 2011 at 6:06 pm

    Ok. Ok. I knew I was going to get into trouble throwing that out there ;). And of course I wouldn’t expect it to be like BabyG. But I just wanted to let you know that if there were a way to make money so you could be more free to “pursue your passions,” then this reader, at least, would be Ok with it. But I get. And I wont mention it again. Promise.

  • Jenna April 28, 2011 at 6:25 pm

    Justine, don’t feel bad for bringing it up! It’s a totally valid question. And I will never say never. But I guess I feel that since I have other means to make money right now, it doesn’t feel right on this space since it’s a personal blog….

  • Cookie monster April 28, 2011 at 6:35 pm

    Your blog is awesome. I just love it. You write with a clear, honest voice and your pictures are amazing and beautiful. What about a “how-to” documentary style book? Maybe how to run a small business. Something different and more creative than your typical “how-to” book with lots of personal stories intertwined. Something that is more from the creative or artistic or lifestyle perspective of running a business. Thank you for your blog in the meantime!

  • dee April 28, 2011 at 7:47 pm

    I have a wise friend who recently explained to me that much job dissatisfaction arises from the mistaken belief that our careers should be upward trajectories (with similarly upward incomes). In fact, she said, for most people there is an upward slope the first ten years, and then a plateau the rest of the career. Knowing that is the most common scenario was quite comforting—I’m now looking to find some additional satisfaction outside of my career, and feel much freer without the burden of trying to grow my income.

  • veggietestkitchen April 28, 2011 at 8:03 pm

    Jenna, I’m surprised you haven’t been offered a book deal yet. Our lives are so different, and I generally could care less about family issues (seeing as how I don’t have one) but I LOVE reading your blog. Everyday. Just for the pictures and the stories. I’m sure there are enough out there who think the same and who would support a sweet fine book =)

  • Jenna April 28, 2011 at 8:21 pm

    @veggietestkitchen Thanks for that lovely comment. I’m not sure what a SweetFineDay book would be about though!

  • Lakshmi April 29, 2011 at 2:55 pm

    Me too, Jenna. Taking pictures, telling stories, connecting the both to people.

    Finally, got my website up and am able to fill in the ‘website’ field correctly on your blog space! I think I always mistook that as the ‘Subject’ field… 🙂

  • Lakshmi April 29, 2011 at 3:01 pm

    Another thought.

    Why don’t you (rather, can you PLEASE!) tag some of your ‘clothes’ posts? I love your style and would love to see/know more of your style choices, layering, outfit combinations, etc.

  • Mef April 29, 2011 at 6:37 pm

    more on your thought process when taking pictures. love you style.

  • patricia April 29, 2011 at 9:40 pm

    I can relate to this so much—but there are some differences. I have found what I’m more passionate about aside from design. My problem is that I need to make it a financially stable situation. Even though my design work is where most of my income comes from, it no longer thrills me the way it used to. I feel like I can climb so much higher and yet I feel like you—I’m moving laterally. I’m still trying to figure things out.

    Your idea to develop your story telling with photography is really spot on. I agree with all the comments—you have such a gift with writing and with images. I can’t wait to see where it leads you.

  • Alicia May 1, 2011 at 12:34 pm

    I think you’ve written about fashion a little bit in the past and maybe I’m just forgetting the specific posts, but just writing to say I love what I can see from what you’re wearing in that pic, so cute!! 🙂

  • Jenna May 1, 2011 at 10:39 pm

    @shruthi thank you for passing on that award.
    @Lakshmi, I don’t think there are enough “clothes” posts for me to tag.

  • Lakshmi May 2, 2011 at 1:24 pm

    Well, then create a series of such posts, maybe? Would love to see them.

  • Rita May 2, 2011 at 7:01 pm

    Oh, my friend, you and I are in the same pattern of restlessness and doubt. Except I’m on the other side, working for corporate America. If it helps, the praise and promotions are not as frequent in this climate, and I quite envy how you have more freedom. What am I passionate about doing? I could take pictures all day, every day. And make paintings. But can I do both just for me, and not for clients who have very specific needs?

  • Thaddeus Teppo July 24, 2011 at 2:14 pm

    I recently came across your web site and have been reading plenty of posts of yours. I just thought I’d add a fast comment and let you know that you’ve got a truly nice weblog. I’ll watch out for updates from you!

  • ulga dla inwalidów November 29, 2011 at 7:37 pm

    I’m a freshman in college and I was planning on majoring in Computer Engineering, but unfortunately it doesn’t really seem too interesting to me, especially all the computer programming. I’m considering changing my major to Computer Science except I don’t really know what kind of career a degree in Computer Science will get me. So what is the difference between the two? Please help me out, I don’t really have too much time to ask the advisers at my university, so any help would be appreciated..