The Careers You Won’t See on my Resume and Why They are Important

“The fastest way to succeed is to double your failure rate.” — Thomas Watson, Sr. (IBM)

Photo by Andrea Piacquadio

He was talking about products and innovation. But, I think it applies across the board of life, and most especially in your career journey.

Something that isn’t on my resume, that I don’t often share but realize I should, is that I held nine different career-level jobs in a three year timespan, before starting at Microsoft. NINE.

Here’s where I worked, how long, and how it ended:

Wilmington, NC
EMEC — 1 year (laid off/let go)
Winglish — 3 months (quit)

Atlanta, GA
Mac McGee’s — 6 months max (quit)
Insight Global — one week (quit)
Tech Recruiting Firm — one afternoon (they decided to go with a different candidate)
The Metropolitan Club — 3–5 months (quit)
Continuous Health — 9 months (quit)
CallRail (tech start-up) — 3 months (quit)

Wilmington, NC
EMEC — 4 months (part-time/temp)
*ya, the company that let me go

Roadtrip USA (not a job, but a literal road trip that I took after accepting, but prior to starting at MSFT) — 3 months
Microsoft — 6 years to date (still here)

Until I wrote this, I had no idea that I had really worked that many roles for that many companies in such a short timespan. But, I can tell you that if I could go back, I would do it all over again.

Here’s why and what I learned:

1. It’s okay to move around in your career. It’s okay to experiment and to explore. It’s okay if you want to try something new, hate what you are currently doing, not a good fit for your current thing (or the next thing or the next thing). It’s okay if you quit early and it’s okay if you get fired. You don’t have to work in the same job, or for the same company until you retire.
2. By ‘failing fast’ and pivoting into and out of so many different roles, I was quickly able to discover and understand 3 things:
   — My disposition: what I enjoy (and don’t enjoy) doing
   — My skill set: what I am (and am not so) good at
   — My priorities/trade-offs: what I believe is important (or not at all) in my career, life, & in places of work
   For some people, it takes years to learn these three things. And it was the discovery of these things that allowed me to become very intentional about my career and my growth in the early stages of my career. AKA — I have no regrets.
3. By listening to my gut, each of my jumps were jumps up and into expansion of some sort. I didn’t move just to move, but I did move when I felt that it was right. With each move, I gained deeper experience, cultural value, a raise or promotion — all things that I wouldn’t have expanded into if I didn’t listen to my intuition and follow it. Not to mention — had I not jumped, I wouldn’t have made it to Microsoft. I wouldn’t be where I am today.
4. People went bonkers. No one knew what to think, or what I was doing, and everyone was worried about my resume. I learned to be really resilient to criticism and unsolicited advice. PSA: The concerns of others didn’t matter. Not all of these jobs made it to my resume(today), and my resume is a-okay, TYVM.

When we listen to our intuition, take the time to learn what we like, where our value is, and get clear on what matters to us, we can move from a place of total confidence that transcends even the opinions of others. Not only this, but we can move quickly. We can tolerate when we fail because we are moving from something deeper than a false sense of success.

In the practice of growing ourselves, it is like any field or industry: if you fail fast, you’ll succeed even faster. If you can become absolutely tolerant to failure, your growth is uncapped.

Don’t be afraid to make a move in your career, to try something new in your life, to put yourself out there in some way. The job title doesn’t matter. What other people think is keeping you small. Focus on yourself.

What do you like?
What do you want to do?
What are you capable of doing right now?
What’s working and not working?
What can you change?

Start asking yourself these things now because a year from now, you will thank yourself EVEN (especially) if you aren’t still doing the same thing next year. Expansion starts with introspection and becomes reality through action.

That thing you’ve been thinking about doing, do it. No one is keeping score, I promise.