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The Best Career Advice I Ever Received


I recently watched a TED talk by Drew Dudley and it’s a great talk about leadership, but a question he posed in it made me reflect on my own life. He said,

How many of you guys have a lollipop moment, a moment where someone said or did something that you feel fundamentally made your life better?

It struck me mostly because I had been thinking this past week about the things that have led me to where I am today. It’s still pretty early in my career, but I definitely have had my own lollipop moment.


My last year of college at UofA, I spent most of my free time applying to jobs. I can’t even remember how many I applied to and how many interviews I went on. I remember it being the worst because I was about to be a new college grad with no internships under my belt and the only relevant work experience I had was working part-time at an IT Help Desk for one of the colleges on campus.


Tech interviews were especially stressful because I’d often get asked to write some code on the spot or verbally draft up some logic over the phone. It didn’t help at all that I suffered badly from Imposter Syndrome, but I sucked up my nerves and went through every interview I got hoping that somebody, anybody, would say yes. At the end of every interview, they always asked if I had any questions and my favorite one to ask was this:


What’s the best career advice you have ever received?


I’d get great reactions and thoughtful answers – I really wish I remembered them all. But there was one answer in particular that’s stuck with me.


I was interviewing for a Software Developer position in Ithaca, New York. I had interviewed with one other person in the company and they wanted to set up a second interview with their Vice President at the time; she had seen my resume and wanted to speak to me herself. We had a great conversation; she seemed intrigued by my background and satisfied with my answers.


When I asked her what’s the best career advice you ever received? she replied:


Never take a job that you know how to do.


I was confused by what she meant and she explained, when you take a job you already know how to do, you’re not learning anything new. It doesn’t mean take a job that you’re absolutely unqualified for, but take something you can learn and grow in.


I was surprised – and relieved. Mostly because I had felt so unqualified and inexperienced for most of the jobs that I was interviewing for, but also because it put things into perspective. It’s guided me every time I’ve come to a crossroad in my career. Every time an opportunity came up, I’d be scared that I wouldn’t know what I was doing and the advice always came to mind.



There have been several times where I felt completely inadequate. Like I wasn’t smart enough, wasn’t good enough, or I didn’t deserve to be in that position, but I’d remind myself that it’s okay to not know everything. I’d take a step back and realize that the few things I didn’t know how to do, I could figure it out with some help and guidance. Pretty soon, those ‘unknowns’ became familiar territory.



In Sheryl Sandberg’s book, Lean In, she brings up research that found that men apply for a job when they meet 60% of the qualification, but women only apply if they meet 100% of them. It’s surprisingly true. I know that I’ve felt that way and I’ve even seen this in practice – my male friends have much more confidence applying to jobs than my female friends.


That confidence comes with time, experience, and a little bit of faith in yourself. I’ve found that as long as you have a great attitude, a willingness to learn and work hard, you’ll figure it out. Don’t be afraid to take that job, or at least apply for it! You never know – it might just be exactly what you needed.


I ended up not getting an offer for that position. They had asked if I was willing to relocate and even though at that point, I would’ve gone anywhere, it probably wouldn’t have been the best decision. I think they were willing to give me a chance, but in hindsight, they knew it wouldn’t have been the best fit for me. I didn’t even have a clue where Ithaca was and having a little Hawai’i girl moving from Tucson, Arizona to upstate New York would’ve been some serious culture shock.


It’s kind of crazy to think how much of an effect that lollipop moment had on my life. I doubt that VP even remembers interviewing me. You never realize how much of an impact that moment makes until much later, but in retrospect, it ends up being so sweet.


Have you had a lollipop moment?
 What’s the best advice you’ve ever received?
 Share with me in the comments!

By Roxy

Roxy is a millennial minority woman in tech and first time mom. Born and raised in Hawai'i, she currently resides in the DFW Texas area with her husband and daughter.

7 replies on “The Best Career Advice I Ever Received”

Roxy this is truly a great post. It was engaging and really hit home to me. I write about women empowerment and about the tremendous gaps in the markets that are currently in demand. The person that gave you that advice is filled with wisdom. You seem to be young and super intelligent. The confidence and experience will come. However, vision, a keen eye and open mind and heart to take in what’s right and asses situations doesn’t come naturally to some. That’s an advantage you have as well. I am subscribing to your blog and hope to read more inspiring stories like this.

Aw, thank you Emely! Your comment really meant a lot! Where do you write? I Feel like there’s not enough real inspirational content out there about women empowerment and I’d love to subscribe to you, too.

The best advice I ever received was to stop over analyzing and just start doing. Sometimes we get caught up in all the what if’s. The world could use more do-ers.

Gosh that does sound like great advice! It makes sense to seek jobs where you can also grow your skills. I’m going to share this from now on , thank you for sharing this!

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