How to Get Out of a Career Rut

October 11, 2018

How to Get Out of a Career Rut I wit & whimsy

When I was preparing to be self-employed (a period of six months during which I did a lot of networking and preparation) I penned an article for Create & Cultivate called 5 Ways to Prepare for Self-Employment. Selfishly, I think the act of writing it was therapeutic for me. And it must have done well for C&C as about every six months they re-publish and re-promote it and I know when this happens as my inbox gets hit with several emails immediately with people feeling stuck in their careers, curious about self employment or newly self employed – all seeking advice.

How To Get Out Of A Career Rut

Blazer + Ponte Pants I wit & whimsy

How to Get Out of a Career Rut

Ann Taylor Factory Blazer + Ponte Pants I wit & whimsy

Ann Taylor Factory Plaid Blazer + Ponte Pants I wit & whimsy

How to Get Out of a Career Rut

One such email struck a chord with me recently and around that time I also attended an event at Crate & Barrel featuring some amazing career women (Reese Witherspoon, Crate and Barrel CEO Neela Montgomery and Poshmark co-founder Tracy Sun, all moderated by former EIC of Teen Vogue Elaine Welteroth) with conversation surrounding courage in career and the two cases inspired me to pen this post about how to handle a career rut. We’ve all been there.

Things at work will feel like you can’t go on. Getting out of bed in the mornings seems unbearable. You’ll loathe Monday mornings. Your boss is driving you nuts. You suddenly hate your job more and more. The clients are driving you nuts. Your hours have become insane. You’re questioning every career decision you’ve ever made. You don’t have any sense of work life balance. You want to cry or pull your hair out. Or both.

My best piece of advice for feeling like you’re stuck in a career rut?

Grant yourself the time and space to explore other options. Take it as an opportunity to learn. And I don’t mean using your lunch break to scan But rather get out of your comfort zone and take time to really ask yourself what needs you have that aren’t being met. Research other industries. Research other careers where your skill set could be applicable. Read a lot. Books, articles. Watch TED Talks, listen to podcasts. Consider a solo trip to give yourself a new environment to consider your choices. Surround yourself with information and opportunity.

Then, take a step back, and allow yourself to listen to your heart and your gut instinct. My gut instinct is what led me to be self employed in the end. (And man have I learned a lot since choosing it!) Job satisfaction is possible! But sometimes it takes time to find it. And a lot of patience.

And I thought I’d share the email I received and my response to the person who sent it to me as I think it is broadly relatable:

I have been having quite the career struggle and dilemma over the last few months, and recently read your blog post on Create + Cultivate about self-employment. I went to school to do graphic design, and have worked for a home improvement e-commerce company as a visual designer for the last two years. I’ve only been out of school for about a year, and just moved to LA a few months ago.

>I imagined moving to LA would give me endless opportunities and new connections. However I’m having issues even getting my resume read by someone. I started a job here about a month ago, and decided it wasn’t a good fit for me after about two weeks. There were some serious issues with the management, and I was very uncomfortable with the way the art director spoke to women in the office.

Anyways, long story short I’m struggling to find my next move and having some serious career doubts. I am a creative person naturally, but don’t always enjoy hiding behind the computer all day. My previous job gave me the opportunity to work on photoshoots and with the marketing team developing campaigns, so I got a wide range of projects throughout my work week.

I’m feel as though I’m in a serious career rut, and I feel like I’m too young to say that haha. I read your post and it inspired me to reach out because it sounds like you’ve been in a rut before. I feel like I don’t have enough experience to jump out on my own, but I’m having issues finding a position that seems fitting for me…

From your experience and all that you’ve learned is there any great advice you could give me? I don’t know very many people in my industry and need some guidance or at least someone to tell me that what I’m going through is normal.

Glad you enjoyed reading my post and do know that career ruts or stagnation are totally normal! This won’t be your last and that’s ok. The good news is that there are lots of jobs out there especially for people with design experience. Since you hold a valuable skill it may help you to pick up some work on the side as a freelancer helping companies that need extra assistance or even bloggers who want to up their design presence.

Doing freelance gigs can greatly expand your network and could even turn into something full time! Check sites like Upwork to see who may need help and tell everyone you know you’re looking for extra gigs. I got all my client work at the onset from my network and continue to see word of mouth & personal referrals as my #1 driver of business. The best jobs don’t come from job postings, they come from who you know. So my best advice is to get yourself out there! Attend networking events, join Facebook groups (C&C has one – are you a part of it?) and meet as many people as you can.
See someone who has a job you think you’d like that’s also in LA? Reach out and offer to buy them coffee or lunch. A few may take you up on it! Send personalized notes through Instagram or LinkedIn. I do this all the time. And for every meeting I took, that person introduced me to someone new so my network continued to grow. It’s a sign of strength to ask for help and guidance! And the good part is, everyone loves talking about themselves and these types of meetings allows them to do so 😉 Consider attending a C&C conference or something similar and put yourself out there to meet as many people as possible. Are their graphic design groups on Facebook or Linkedin? Are there companies you admire who are doing great things in the creative space? Find a way to meet people at those companies.


Finding the right job involves a lot of putting yourself out there.

When you do, your network will expand and therefore so will your opportunities! Never be afraid to cold email someone. (I can already tell you’ve got good instincts just by sending me THIS email!) All the efforts will pay off in the end. And remember – the power of positive thinking! In fact, it’s one of the things I have to tell myself all the time on the tough days. Put good out = get good back.

Career ruts are tough and they can seem like they go on for forever. And one last piece of advice – no matter how unhappy you are in your current job – don’t let your colleagues or boss see it day to day. When the day comes that you’re gone you want to be the person that everyone remembers as a hard worker. As a contributor. As a go-getter. And as a high performer. Industries are small and so you want to always be remembered well and spoken about highly. Go out on top; not as a person people are relieved to see go.

. . .

I hope that helps for anyone experiencing this sort of career mini-crisis.

Know that change will come along and that your current situation isn’t forever (unless you are complacent in which case you will always be unhappy where you are!) Grant yourself the space and time for change and you’ll be well on your way to a new, exciting chapter in your career.

As for this outfit…did you guys know Ann Taylor Factory is now online?! They were kind enough to let me pick a few pieces from their latest arrivals and can we have a moment for this plaid jacket!? It is perfectly oversized (I’m wearing a Small) and the quality + price are awesome. (It also got an amazing response on Instagram immediately, too!) Other great items I spotted on the site were these faux leather leggings, this sweater, this top, this lace trim cami, this coatigan, these pants and this amazing suede moto jacket.


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