Ask Me Anything | The Courage to Change Career Paths

Today’s reader Q&A is all about career development.

Black Convertible Camisole (also comes in white) / Blush Tapered Ankle Pants / White Embossed Clutch (on sale for $45) / Suede Cutout Sandals (all courtesy of White House Black Market)

Before we dive in, I want to give a shout to White House Black Market for sponsoring this post and outfitting me in the perfect summer work outfit. As much as I love dresses and skirts, there’s something a great fitting pair of pants that makes me feel like a boss – and these blush tapered pants are it! I think they’ll transition well into fall, but I love them right now paired with a simple black tank and maroon strappy heels. FYI – the heels run a little narrow!

Earlier this summer, I started a new series called ‘Ask Me Anything’ – basically an extended answers to questions from readers. Today’s question:

“I know you’ve talked about leaving law for marketing, but how did you get the mental and emotional courage to do so? I like my job and think it’s time for a change. Since I’m employed, I know I can be picky about choosing my next step, but I keep second-guessing my credentials when I read job openings.”

If you’re new here, you can read about my crazy, unconventional career path here, but to make a long story short: I graduated law school, moved to NYC without a job, then landed my dream job supporting communications in the retail industry before later scoring the ultimate gig managing internal communications for a major U.S. airline. Whew – still with me?

Truth be told, I don’t consider myself the courageous type. But the older I get, the more comfortable I get with knowing what I want and what I don’t want in life. 

I’d say that halfway through my second year of law school was when I realized that I didn’t want to be a lawyer. The public service life wasn’t for me, but neither was the idea of working for a law firm. I loved school – I even loved studying for the bar exam – but I didn’t want to pursue a career that wasn’t ultimately going to make me happy.

I moved to NYC without a job and one of my very first interviews for was a legal internship in a small law firm in Queens. I was offered the job, but I was going to have endure a hellish 1-hour commute for a job that didn’t excite me. Two hours round trip after a full day of work wouldn’t leave me anytime to pursue anything that I was truly passionate about.

So like with any reasonably sane, unemployed person paying sky-high NYC rent, I declined the offer and took a gamble. I was going to leverage the skills that my legal education gave me (critical thinking, analysis, writing) and take them elsewhere!

To me, it wasn’t courage – it was just what felt right.

If you’re fortunate to already be employed when you’re making this decision, then you have the luxury of time to consider what you really want and how your strengths can take you there. I’d start by making a list of the transferable skills you bring to the table. These are skills you’ve mastered in your current career, but can also apply in completely different roles. Maybe it’s project management, data analysis or the art of  negotiation. For me, writing was the biggest skill that I could offer, which is why communications was such a natural pivot for me. 

In every cover letter that I submitted, I wrote about why I was making the “radical” jump from law to communications, and the skills I had that actually made it a natural fit. It’s not so much about courage – it’s understanding where your skills can take you and then demonstrating that to future employers.

I hope this helps and if you have any more questions for this Ask Me Anything series, feel free to email me at

Thank you White House Black Market for sponsoring this post!

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  1. Maureen wrote:

    What a great post! You are so right about knowing ones skills set and strengths. It works in our favor to know what we are after and even more so in finding our passion. After all, a degree can only take us so far before we really have to take the drivers seat and show the world what we are made of.

    Maureen |

    Posted 8.14.19 Reply