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3 Lessons I Learned from Making a Difficult Career Choice Mid-Pandemic

Changing careers can be hard -- changing careers amidst a pandemic is even harder.

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A lot of people had hard decisions to make during the pandemic — especially women. Although I didn’t have to choose between my family and my career or anything nearly so drastic, I did have my own decision to make. It wasn’t easy, but it paid off in the end, and I want to share that story and what I learned from it. 

I already had a great job working at Deloitte. In fact, I’d recently been promoted and found myself running both the Google Marketing Platform Alliance and the Google Cloud Alliance. I was very visible with the firm and working with some of the smartest and most innovative people in the technology industry. This also meant I was supporting almost a billion dollar's worth of business activity, and that felt pretty amazing. After all, I come from humble beginnings, and my climb up the marketing ranks hasn’t been what you’d call a traditional one. But along came a great company (my current employer Jellyfish) that offered me the global chief marketing officer position. For years, I’d been thinking about if I had what was required to be a CMO, and the opportunity that was being held out was, frankly, nothing less than my dream job. 

At this point, it might sound like the easiest decision in the world. After all, how could I turn down my dream job? Spoiler alert: In the end, I didn’t. I took the job, but making that choice was hard for a number of reasons, most of them related to the pandemic. 

Because of Covid-19, everything was in flux. Adding more instability to the mix when most people were grasping for any kind of certainty in their lives felt not just counterintuitive but borderline ungrateful. Because I’d already seen it happen at Deloitte, I knew that making a big transition against a backdrop of pandemic-induced chaos would not be an easy thing to do. Would I be successful? What would happen if I wasn’t? 

In a business-as-usual context, I would have said “yes” right away, but this was the opposite. I needed the confidence to make the leap, so I dug deep and found it. Here’s what I learned: 

1. You have to bet on yourself

Starting a new job is hard. Being onboarded fully remotely and never actually “meeting” your colleagues is hard. Having to collaborate day in, day out with those same people — without the benefits of seeing their body language and facial expressions up close and in person — is also hard. Navigating time zones from London to Australia while on the west coast of the US is not only hard, it’s exhausting. And, of course, taking on a top marketing role in the middle of the century’s biggest disruption is very hard. 

At the end of the day, none of those things — the job, the people, the uncertainty of it all — are what you’re up against. You’re really just up against yourself. The skills, the attitude, the capability — whatever tough decision or challenge you’re facing, you undoubtedly have what it takes to come out on top. But, you can’t bet on things working in your favor because chances are, they won’t. Instead, you have to bet on yourself. 

Related: 7 Ways to Shatter Your Own Glass Ceiling

2. Don’t underestimate the value of thinking ahead

Even before my first day working with Jellyfish, I had put together a 30-day, 60-day, and 90-day plan for what I wanted to accomplish at the company. To come up with those, I had to ask myself some serious questions. What would success look like if I took this job? What would failure look like? How would I navigate the new circumstances in a way that benefited both myself and the organization? 

It doesn’t matter if you’re pondering an invitation to the C-suite, taking a second job, quitting to stay home with children, or wrestling with some other dilemma. Having taken the time to consider a range of possible outcomes — and how they will affect you — is always helpful. The value of a plan isn’t in sticking to it but in its ability to highlight potential stepping stones or stumbling blocks ahead of you.



Like Dwight D. Eisenhower said, “Plans are nothing. Planning is everything.” 

3. Boundaries are powerful tools

Women in particular have a long history of bending over backward to make their careers fit in with their lives, or vice versa. Progress toward equality has certainly been made, but between women and men, for example, it’s much more common for the former to leave their jobs and take on family duties — a wound that Covid-19 has poured a lot of salt into. 

In this context, boundaries serve two powerful purposes. First, they act like rumble strips — you know, those bumps on the sides of roads that warn you with vibration when you’re outside the lines. When you’ve set firm boundaries, you know when they’re being crossed, and you know that means potential danger. If you haven’t set them, the lines are a lot blurrier.

Second, boundaries create a sort of box, and within that box, you get to enjoy the benefits of flexibility. In dealing with challenging circumstances and finding your way through uncharted waters, flexibility is a must. It’s the freedom to go with the flow — as long as you’re inside the boundary lines. 

Related: 5 Tips for Mompreneurs Raising a Family and Running a Business as the World Reopens

Final thoughts

No matter how you spin it, choosing between two highly rewarding, personally fulfilling jobs is hardly a traumatic experience, and I’m very thankful that the choice was mine to make. I don’t want to compare myself too closely with women — or people in general — who’ve had to make much tougher decisions.

I do think, however, that there are certain parallels worth exploring and lessons worth heeding, and it’s my privilege to use this platform as a way of helping and encouraging others, no matter what they may be facing. So, the bottom line is: Believe in yourself, be intentional, know your priorities, and guard your values closely. With planning and preparation, great things will follow. 

Related: 5 Signs You're in the Wrong Career—And How to Make a Change ...

Sharon Harris

Written By

Entrepreneur Leadership Network Contributor

Sharon Harris is CMO of Jellyfish, working closely with global brands and their millions of customers worldwide to create the perfect digital partnerships. Over the last 10 years, she has operated at the executive level to help brands develop relationships and embrace digital transformation.