When Having A Dream Job Takes Work



Confession: After our 3-week trip abroad I was so ready to come home – but I wasn’t ready to go back to work. It was a depressing realization I made on our flight back to the US and I had no idea what to do with those feelings. I was terrified that maybe I hated the job I had created for myself. In order to keep from having a panic attack at a cruising altitude of 30,000 over the Atlantic ocean I had a glass of red wine. Or four.

After we landed in Oklahoma, unpacked and had a solid 10 hours of sleep I reevaluated these feelings in the safety of my own home. I think it came down to feeling overwhelmed. Overwhelmed by the insecurity that comes with being responsible for your own paycheck. Overwhelmed by all the amazing talent already out there and how little I can sometimes feel (ah, the comparison trap). Overwhelmed by the gap between here and there. Overwhelmed by the idea of starting a family on top of growing a baby business of my own.

But here’s the deal. As soon as I settled back in to my desk all the things Tara and I have been working really hard to achieve over the past year started coming to fruition. We’ve committed to positioning ourselves to creative entrepreneurs and overhauled our website to reflect that bold shift. We’re developing an ECourse (launching in September) to better serve the creative entrepreneurs who can’t quite afford a one-on-one engagement with us but deserve solid branding & positioning of their own (and I’m here to say – branding goes WAY beyond a logo design). We’re turning down work from people like government agencies, law firms and financial institutions with lots of money and great marketing directors but no decision making power. Some think we’re a little crazy for this but we’ve recognized that we’re best suited to work with other creatives like us, the “solopreneurs”, who not only need help with a brand identity but positioning and business visioning. That’s what we’re best at. That’s what makes us happiest. We’re working hard to make Braid Creative a resource and a place where we can celebrate other creative entrepreneurs.

I also had this idea of going beyond blogging and getting more personal with letters that will go straight from me and Tara to you. These are free, exclusive, emails for creative entrepreneurs (and the aspiring artistpreneurs) that will go straight to your inbox – and they aren’t old-school newsletters or regurgitated blog posts – but letters, from us to you. In fact, email no. 2 is going out this morning – in a couple hours – if you’re interested sign up below.

Here’s an example of the first letter you’ll receive, explaining what it’s all about, when you sign up:


These are the things that make me happiest. Sharing content. Writing (I almost think of myself more as a writer than a designer these days, fragmented sentences and all). Genuine connections with other creatives.

All of this to say having your dream job takes work. That’s what email no. 2 going out this morning is all about. And I’m taking a healthy dose of my own advice and working hard to make it all a dream. Because, lately, I have no tolerance for doing anything I’m not in love with – and that’s okay by me.

Do you guys ever feel overwhelmed? What do you do to keep your dream job from turning into a nightmare?

Top photos by the talented and radical Greer Inez.

  1. Naurnie

    I constantly feel overwhelmed and I don’t even work for myself. I think when you’re invested in what you do, when you love what you do, and you’re committed to doing your absolute best, you are always putting some sort of pressure on yourself. I think that means you’re doing it right.

  2. I think what it all boils down to is that work is work. No matter how much you love what you do (and I really do love, love, love my job) there are some days where you wake up in the morning and just don’t want to do it. You can be on vacation and just not want to come back yet.

    That’s not a bad thing, though. I think it’s completely normal. Five days a week (or more!) devoted to one thing is tough. I think everyone would rather just go off exploring or lay on a beach or just sit and not think instead of working all the time. But as you’ve said so well before, it’s all about the balance. We’re not going to be ecstatic every single day, but who wants to be that damn chipper anyway? 😉

  3. Naurnie – I hope so. The longer I do this the more patience I gain. I think a lot of this pressure comes from wanting everything to be perfect right now, rather than taking the time to build the experience and skills it takes to be my very best.

  4. Francine – I think you’re right. The myth of the dream job doesn’t exist when work is work. I think then it comes down to a couple of questions which are:
    1. What am I working for? What does success look like to me? Is it $100,000 a year? Or 8 weeks of vacation? Or 6-hour days? and
    2. Is it worth it? At the end of the day am I proud of the work I’m doing and the people I’m helping?

  5. Thank so much for sharing your insecurities. You are someone that inspires me as a designer and a creative entrepreneur and it’s comforting to know that you go through the same types of feelings. I appreciate that your blog is very real. You don’t sugar coat things. I love it. I’m glad to see that Braid is doing so well!

  6. Kelsey

    Your post reminds me of something my mom always says… To stand upon the mountain, you must walk through the valley. Which is to say, it takes a lot of hard work and patience and keeping the press in order to reach your goals. I think you’re just bushwhacking your way through the valley right now… but you’re definitely on your way! Not sure if that helps, haha. You have my mom to thank for that. I agree with Francine though… work is work and some days you’re just not going to love it. But at the end of the day, if you’re still satisfied with where your priorities are and the direction you’re headed, I think that’s what matters. You’ve set your sights on a good mountain!

  7. Erin – Thank you for the sweet compliments & feedback! While I like to use this space as a place to celebrate the things that inspire me, I also want to keep it real (but also constructive). XO

  8. Kelsey – I love that. And it’s a very literal lesson I learned trekking to Everest Base Camp. Nothing beats knowing that you put in a lot of hard work for such a beautiful view. I think the tricky part is defining what that mountain looks and feels like – that way I actually recognize when I’m on top of it. Ha. Thanks to you (and your mom!) for the comment.

  9. I have been feeling overwhelmed for months and its so comforting to know that I am not the only creative who feels like this from time to time.

    Also I am beyond excited that you guys will be offering an e-course! Its been killing me that I had to postpone working with you guys!

  10. Stacey – *sigh* Well, I can safely say I know how you feel. Do you have any tips for getting through the slumps? Or is it more of a pull-up-your-bootstraps and get-to-work kind of thing?

    And we’ll be here if and when you’re ready for our help! But yes, definitely stay tuned for the ECourses!

  11. As Director of Oklahomans for the Arts, I deal with a lot of strong personalities and personal agendas every day. I deal with these challenges by reminding myself every day about the kids in Cherokee County – poorest county in the state. When I get discouraged, I remember they haven’t heard opera or seen ballet and it always gives me the push to keep on keepin’ on. Thanks, Kathleen.

  12. I’m going to buck the trend and say work shouldn’t feel like it if you really love it.
    I really love what I do and I love it 99% of the time because it keeps my mind and soul full (I’m happiest when I’m creating). The other 1% is sheer frustration that I don’t have more time to “work”. That’s not to say I don’t have a personal life, and I guess at the minute its a rebellion against spending the 9-5 breaking up fights or hustles and trying to make sure sharing and caring is being carried out between my children. I will say that I almost resent not putting them in nursery and being a stay at home mama because I know I could achieve so much more (and be a happier person and therefore better by far for my kids)if work could be done at a normal hour rather than starting at 8pm.
    Kathleen I just re-read your last paragraph and I think you hit it on the head “having your dream job takes work” its the battling through to carve out the space for you to do your “work” not the actual “work” itself.
    I for one am in the middle of re-brand and creation of products for launch and find the work is the business side, never the sitting down to create. If only someone could invent dream Instabusiness hey?

  13. Jennifer – YES. I feel like I failed to mention here (but hopefully it came across) that the ultimate goal is this higher calling of actually helping other people in a genuine way. Nothing is more rewarding than that.

    Nicole – YES. I think we’re definitely saying the same thing here. I think we just need to be careful to define (and redefine) what “work” and “dream job” look like. I guess when I say a dream job takes work I mean it in the same way that a good marriage takes work. “Work” doesn’t have to equal “hard” and success doesn’t have to come with painful due-paying.

    For me it’s been about identifying the parts that fill my soul – which are writing blog posts, emails, connecting with other creatives (like you!), working with entrepreneurs and making an actual difference in their business – that’s what I want my “work” to be. That is my dream job that I could spend all day at.

    Thank you for your comment, friend!

  14. I feel you, sister. You and your sister… Dave and I… we’re both blessed and cursed by the freedom we’ve created for ourselves. Dave and I have a tendency to say ‘yes’ to projects we don’t really want to do… and I think we say yes out of fear. Fear of not having neough money. Fear that if we say no to the wrong opportunity, the right one might not follow. But we’ve promised each other not to do that anymore. We learned two things this summer that are helping with that:

    1. At a yoga class in Mexico, our yoga instructor said, “Remember who you work for.” And he meant it in the large scheme of things: who is your life for? why do you do the work you do? Dave is making us both posters to hang in our offices that say “Remember who you work for.”

    2. We now have a “hell, yeah” policy. If an opportunity doesn’t make us say “Hell, yeah” we turn it down. We’ve spend 20 years saying OK to projects for the “logical” reasons. But we need to be bold and stick to our dreams now. Hell, yeah.

    Love you. You’re are living your life so beautifully.

  15. As per usual, this hit home with me. I was just doing our laundry (out here in Laguna), and thinking…
    I like it out here. Obviously, the lack of heat + ocean are huge components to my happiness out here. But is it because I am “not working” as much?? (I have brought edits out here, but I am not meeting with clients right now.) OH NO!
    Kathleen, you are clearly talented! You are one of the most successful human beings I know! I think part of owning your own business (especially a creative one), is one of the hardest things to do on this planet. We do it in the same way we live life! We do it to the fullest. And we insist on even acquiring more/better for ourselves. We want to get the most out of this life. But there is that fine line between not enjoying your beautiful life/career you’ve created & being motivated/driven to be better!
    Just as every situation is complex and unique in itself, I am not trying to narrow down your feelings to just this, but sharing something I was thinking about this morning…
    Adore you! You are such a gem!

  16. Tara

    I own my own biz and have been feeling a lot of these things lately too. I’ve been feeling extremely overwhelmed lately, which has turned into kind of a lack of motivation. It’s weird, and I feel bad complaining about how busy I am, like it’s a bad thing. I’ve come to learn that growing your own business means constantly feeling both extremely lucky and cursed at the same time.

    I love knowing that I’m not alone! Thanks for posting about this!

  17. HAILEY

    Kathleen, you are constantly a refreshing breath of fresh air for me. Thank you.

    1) I’d love to be on the mailing list. Please sign me up. (haileykingphotography@gmail.com)
    2) I still want a logo design by you. I want the branding/consulting too, but still can’t afford it. Lets please talk.
    3) If and when you have a baby, I really, really want to photograph you.
    4) Yay for keeping it real. I could not relate more with being overwhelmed, trying to make my dream not turn into a nightmare, and also the “comparison trap.” Scary stuff. Glad to always be reminded that I’m not the only one.
    5) I love the braid creative blog. Keep it up!
    6) Welcome home. 🙂

  18. Thank you so much for this! Your vulnerability and honesty is completely refreshing. I’ve been feeling super overwhelmed lately… as a creative, a designer, and a freelancer, I look around and see so many people doing the same type of job and they just seem so put-together and so much better at this. I just can’t help but think, “Everyone has their shit together but me!!” When really, that is so far from the truth. We all struggle, we all feel inadequate at times, and there are days where we all wonder “what the hell am I doing?”…it’s always encouraging when a fellow creative shares these feelings, to let us know that we’re not alone. Thanks, Kathleen, I needed this today. 🙂

  19. tfh.

    This is an AWESOME post. I myself am trying to change direction as far as career goes and it’s tough to imagine doing so being a new mom and all. I’ve only worked really lame jobs to pay the bills (i.e. clerk at a debt collection law firm — yuck) but know that I am so much more suited to a creative field; it’s deciding what to do that’s so difficult and once I figure it out, knowing how to make a living from it. Thank you for this. I am so excited about your emails!

  20. Kelljo

    Ha! I decided to check your latest posts since I ran into you this eve and totally understand now where all your questions regarding Eames were coming from. Not sure if I was clear but he is the best decision I ever made. He gives me more motivation to do my best at everything, my work And most importantly my marriage. Also, please tell Jeremy that when I use the word nerd it’s a term of endearment. I’m smitten with a big ol nerd myself!

  21. Mel – Oh, big hugs to you. It’s amazing how many of our decisions are made with fear in the forefront. A couple things I always ask myself are:
    1. What would you do if you weren’t afraid? and
    2. Who are you working for?

    I say hell yeah to working for creative entrepreneurs. To making this world a little braver one person at a time. XO

    Mama hus – Oh, I miss your face. I cannot wait to brainstorm and chat and scheme with you.

    Tara – Yes, it can feel like a blessing and a curse. You’re so not alone in that!

    Hailey – Gah, I’m so sorry for not sending you more info before I left for Europe. I’m shooting you an email TODAY. And of course you can photograph me if/when I have a baby! I would be honored.

    Kelly Ann – You’re welcome. I’m so grateful that this space and everyone that visits here lets me process and work through these feelings as they surface. But yes, you’re definitely not alone in feeling like you don’t always have your shit together. Fake it ’til you make it, right!?

    TFH – Sometimes the hardest part is figuring out exactly what you want! Use this time to explore and soul search what direction you want to go in – and then it’s all about stick-to-itiveness.

    Kelljo – See, I’m obsessed! And OH MY GOD. Eames is THE cutest baby ever. He was so sweet and you are such a fantastic mama! Jeremy knows he’s a nerd and wouldn’t take it as anything but a compliement. 😉 XO

  22. I don’t think I got email No. 2. Do I need to sign up for the list? And I love this idea. Okay, now I’m feeling massively overwhelmed by all I want to do and I can’t sort through it. (I’m nearly in tears right now.) So, yeah, overwhelmed definitely. But I don’t think I’d feel overwhelmed if it all wasn’t worth it, and that’s what pushes me through.

  23. I love that I’m not the only one freaking out – I am currently in a full time paid job and keep bouncing around the idea of being my own boss but it doesn’t really happen because I start worrying about whether I can do things or not.

  24. Just signed up for the newsletter and exciteda about the ecourse. Hopefully (or not) I’m still gainfully employed in time for it.

    I think on the working for yourself front, it’s about the passion piece. And that happens whether your dream job is working with/for someone else or working for yourself. I often catch myself wishing/hoping/dreaming (ie, being on the LOW end of the accountability ladder) that I worked for myself doing the creative stuff I love. For the same reason I don’t really live up to my potential at my “job/job”, I still have not just gone on and DONE the creative leap. I’m super passionate about the work (education and creativity) and that pressure of “living up” makes the dream job totally hard.

    It was never really all that hard for me to get up and go to work when I stocked shelves in the orgo dept of a big chain grocery store. I wasn’t passionate about it, it kinda mattered, but really didn’t. And yet in still, I find myself fantisizing about that being my dream job – no pressure, just get it done and then have time to live life to the simple fullest.

    Alas (smile).
    Therapy session complete (smile).


  25. marylynn

    I’ve just started doing business coaching, trying to focus on people who are doing creative work or themselves working in the arts. One of the things that’s a universal struggle and that we talk about all the time is how gobsmacking it can be to find out that this thing you decided you must do – your calling – is a whole lot of work. And work that isn’t about the work you feel you mean to being doing, instead it’s all that boring “business-y crap”. It’s a shock to many entrepreneurs and a difficult thing to work through. It sounds a little like you’re hitting that wall but pushing through nicely.

Leave a Comment