Career Advice for Lost Twenty-somethings

Me at my college graduation in 2012

In my twenties, I’ve felt so much pressure (both internal and external) to find the right career. I think most of us have.

Since graduating from college, I’ve worked in sales and marketing. I’ve freelanced and blogged and au paired. I’ve entertained many, many career paths, from journalism to the foreign service. At many points in my twenties, I’ve wondered which professional path is right for me.

Now that I’ve finally figured out what I want to do (I just started grad school!), I wanted to dole out some hard-won career advice. Finding the right career path can be agonizing, so I wanted to share what worked for me.


Here are some ideas if you’re feeling lost:

If you’re still in college, do as many internships and extracurriculars as possible. Switching jobs and careers is difficult, so experiment as much as you can before starting your career.

Take the Meyers Briggs personality test. The Meyers Briggs is a test that helps identify your strengths and weaknesses. It helped me figure out why I flourish in certain areas (brainstorming) and flounder in others (repetitive tasks) — classic ENTP over here! You can take the test for free at

Follow your gut, even if it goes against conventional ‘good’ advice. When I was in college, I turned down an internship with the Chicago Tribune. Instead, I decided to work at a startup, where I managed their blog and learned WordPress. This later gave me the confidence to start my own blog, which led to so many wonderful opportunities. In the long run, turning down a prestigious internship was 100% the right choice for me.

Think critically about what you value in a job. I recommend making a list of all the jobs you’re ever worked and listing out what you loved and hated about each of them. Write down everything you’re good at as well as what other people say you’re good at.

I did this, and realized I need the following things in my career: to feel respected and valued, to have creative freedom, to work with other people, to feel like my work has an impact, and to be well-paid. Your priorities will probably be different, but it’s important to be honest with yourself about what you need in your career.

The view from my office in Boulder

Realize you’re never going to find the perfect job. The expression “do what you love and you’ll never work a day in your life” is totally misleading. Unless you are passionate about “invoicing, meetings, and taxes“, you’re going to dislike some part of your job. It’s called work for a reason.

Know that you can do anything, but not everything. For a long time, I stalled in my career because I was afraid to make the wrong choice. But as Sylvia Plath’s fig tree warns us, by failing to choose, you miss out on opportunities anyway.

Think carefully before going into significant debt. I never saw myself going to grad school because I was afraid of putting myself in debt. I am now only going to grad school because I know exactly what I want to do with my degree.

Consider starting a blog. Starting a blog was one of the best things I’ve ever done. It gave me a creative outlet, introduced me to some of my best friends, and helped me hone my writing and photography skills. It’s also been very useful professionally (it looks great on a marketing résumé, for example), and earns me passive income every month. I know blogging isn’t for everyone, but it may be worth considering if you like to write, share, or build things.

Understand that only you know what you want. Other people may have suggestions for what you should do with your career, but they are just that – suggestions. In the end, only YOU know yourself, your abilities, and your goals.

For example, growing up my dad always told me I should be a dentist. As a creative, absent-minded klutz, I’m very glad I didn’t listen to his advice (I would be the worst dentist ever).


Here are some resources that helped me find my way, and may help you find yours:

Am I There Yet? by Mari Andrew

You Are a Badass by Jen Sincero

The Defining Decade: Why Your Twenties Matter (this book gave me a heart attack about my career progress, but I’d still recommend it nonetheless)

How to Be a Person in the World by Heather Havrilesky

Any article about successful people who got started later in life – did you know Julia child was a spy before she was a cookbook author?

The Fringe Benefits of Failure, J.K. Rowling’s Harvard commencement speech (pretty sure I watched this at least 10 times while job-hunting)

Anything by Cheryl Strayed or Brené Brown or Haley Nahman, a brilliant writer at

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And in case you were wondering, here’s my very windy career path in a nutshell: I got a bachelor’s degree in advertising, thinking I would become a copywriter. Instead, I moved to Paris to au pair. On the side, I started a travel blog. After a year in Paris, I spent a year traveling Europe, India, and Southeast Asia, freelance writing and blogging along the way to earn money. I soon realized working as a digital nomad wasn’t for me, so I decided to pursue a traditional career. I landed a sales job at a digital advertising company in Colorado. A year later, I was promoted to marketing, which was a much better fit. Then I took a job at a startup in Kampala, Uganda. It was there that I tried my hand at UX design, which I really enjoyed, so I decided to apply to a UX design program at the University of Michigan. I got in, and that’s where I am now.

. . . . . . . . . . .

So, more a thousand words later, that’s everything I know about finding the right career! I would love to know — what do you do, and how did you get there? Did you know what you wanted to do from a young age, or did you have a more circuitous career path?

P.S. How to Find a Job after a Gap Year and Is It Smart to Travel Young? A Follow Up Five Years Later.

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About Ashley Fleckenstein

Ashley is a travel and lifestyle blogger who lives in Ann Arbor, Michigan. Since college she has au paired in Paris, backpacked the world solo, and lived in Uganda. Her work has been featured by Buzzfeed, Forbes, TripAdvisor, and Glamour Magazine.

3 thoughts on “Career Advice for Lost Twenty-somethings”

  1. Thank you SO MUCH for writing this post. Came when I needed it most! Currently a semi-lost 26 year old with way too many different interests and have changed my mind about a billion times concerning my life path. I also love Haley Nahman! I relate to pretty much everything she’s written (that I’ve read anyway). Going to check out some of your other suggestions – thanks again, and good luck in grad school!

    • Hi Kelsey, I’m so glad you found it useful! Isn’t Haley Nahman the best?! She needs write a book already. Good luck with everything — in your career and otherwise :)

  2. Great advice, Ashley! I’ve going from the traditional office job, to teaching abroad, to another office job, and then going back to school to get my teaching license. Now, I’m teaching ESL in the US and working with students from all over the world. I learn new things about my students’ cultures and the world everyday. Is this what I want to do forever? I don’t know. I’ll be 30 next month and am still trying to figure everything out, but I agree with you that you should follow your gut, even if everything about that feeling is unconventional and goes against what others say.

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