What I Learned From Starting (and Quitting) a Job Remotely

When exploring new roles remotely, learn from my mistakes.

Anita Ramaswamy
Feb 10 · 4 min read
Photo by Magnet.me on Unsplash

I started a new job remotely in the middle of the pandemic and quit five weeks later. After months of interviews, case studies, and intermittent identity crises, I landed what I thought was my dream role in October. I had previously worked in finance for a year and some when I realized that I was no longer passionate about it. Grueling work hours aside, I could not quiet the thought in the back of my head that I wanted my life to serve a greater purpose beyond putting together fancy PowerPoint decks.

As a lifelong try-hard, I didn’t want to sacrifice the prestige that came with such a sought-after (and well-compensated) job. I thought the trite advice about following one’s passion only worked for those with generational wealth. So instead of listening to the voice in my head that told me I wanted to find a truly meaningful job, I thought I would compromise. I found a middle ground within the same field, which I thought was better aligned with my interests and compensated at a similar level. I was thrilled when I landed a role at a prestigious firm in the midst of a difficult job market. My elation as I advanced through each subsequent round of the process coupled with the haze of Zoom interviews clouded my judgment. In my excitement, I overlooked many signs that this was not a good fit for me after all. When exploring new roles remotely, learn from my mistakes, do twice the amount of diligence, and be careful what you wish for. Here are some things I wish I had kept in mind during the remote interview process.

Don’t run from something; run towards something.

My first role out of college was a poor fit for my interests, so it was difficult to get through each day. This feeling is not unique. 43% of millennials plan to quit their current job within two years, according to a 2018 Deloitte survey. I made the mistake of running away from a job I disliked to the first viable alternative I could envision rather than seeking specific positive qualities from the next role. If you are desperate to run away from a position you dislike, you might rush into an even worse fit. Rather than using escape as your motivation, think of what inspires you to move forward. You must be willing to be patient even if the journey is not as simple as you had hoped.

Culture prevails, but honesty about it is scarce.

As with first dates, both parties put on their best faces during interviews. Candidates seek to highlight their achievements and downplay any constraints, while companies present the rosiest possible picture of their culture. One friend recently shared a great tip with me for gathering an honest assessment of a company’s culture, including the downsides. This friend also started a job remotely during the pandemic. Before joining, he spoke to a few junior professionals who had left the company at which he planned to start, asking them how they felt about their time there. Those who have already left are far more likely to be frank with you about what hurdles they faced and, ultimately, what factors led to them moving away from the firm. This friend did not have any pre-existing connections within the company but he had identified these individuals through a Linkedin search, and as a result, he had a much better sense of what to expect from his new firm’s culture before he joined than I did.

Know (and communicate) your limits.

When navigating an unfamiliar work culture remotely, it is even more imperative for both parties to set clear expectations. Sometimes this means you will have to draw boundaries at work. Doing so can be extremely difficult in a remote environment as managers tend to assume that you have nothing better to do than to hover around your computer waiting to be assigned work. While it is important, especially as a junior employee, to pull your weight and prove yourself to a new team, be wary of environments that would set you up for failure by asking the impossible from you. If you have constraints around family time, mental, or physical health, or any other personal issue, be honest with yourself about what these constraints are going into your new role, and do not hesitate to ask questions about how the company handles work-life balance. It is better to clarify expectations beforehand than to over-promise and under-deliver.

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Anita Ramaswamy

Written by

Journalist, career coach, & recovering investment banker. Writing about work, business, politics and social change. anitaramaswamy.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +788K followers.

Anita Ramaswamy

Written by

Journalist, career coach, & recovering investment banker. Writing about work, business, politics and social change. anitaramaswamy.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +788K followers.

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