Don’t Rock the Boat: How I Learned to Make Taking Risks Feel Less Risky

During the chaos of the pandemic, Erin faced job uncertainty and the loss of her biggest role model. These events forced her to come to terms with her fear of risk and change. Here's what she learned from the experience.

Don’t rock the boat. That was the answer I got most of the time when I asked my dad for advice. 

When I was offended by the way my boss talked to me at my part-time job in high school and college, my dad said to hang in there. I toughed it out until I graduated 6 years later.

When I was being overworked and underpaid at my first full-time job, he told me to stay, even after a surprising pay-cut made to prevent layoffs. I worked that job for 5 years.

I’ll admit: I consider myself risk-averse by nature (and nurture), but I often resented my dad’s advice. I knew where it came from. He was the victim of an early-career layoff. It left him with three young daughters, a wife without much professional experience, and a new mortgage. 

He wasn’t out of work for long. Still, the experience shaped his professional life, and the advice he gave me. 

In 2020, this advice and mentality came back to haunt me again. I was working from home and though I wouldn’t have admitted it at the time, I was terrified everyday that I would be laid off due to company-wide cutbacks fueled by the pandemic. I worked harder than ever, often getting online before 7am. I was scared to take time off, and too nervous to ask for a raise despite taking on significantly more responsibility. Things were already so turbulent, I definitely couldn’t afford to rock the boat.

By early 2021, I felt burnt out, but there was still so much uncertainty. I knew I was valuable in my current role, and even if I wasn’t happy, at least I had a job. 

Those would have been good enough reasons for me to hang tight and stay. But, on top of all of that, my dad was dying, and I was trying to come to terms with it.

He had lung cancer, and after three years there was nothing else to do. He was on oxygen and unable to work anymore. The day he told me he wasn’t going back to work was the first time I considered that my dad might actually die. He made every effort not to rock the boat, even through the progression of his disease. 

I am not an eternal optimist. I am not someone who thinks cancer won’t kill someone just because they are someone I love, or because the person is too good, too strong, too important to everyone around them. Still, despite being a realist—maybe even a pessimist—I never let myself consider that my dad would die until it was happening in front of my eyes.

My stable boat was swaying. I casually looked for a new role, more as an escapist exercise than anything. Then I found something, and for the first time in my career, I knew I was perfect for it. 

I didn’t ask for my dad’s advice this time. My heart broke at the prospect of asking him to imagine what my life might be like after his death, plus I knew what he’d say.

I also did some other things that he would have advised against. In my interview, I explained my dad’s situation. In his book, don't rock the boat meant not letting your employer find out that you have a personal life. Especially if it’s complicated. And especially during an interview. Why would a company want to hire you if you need accommodations, even for a short time? I also expressed clear salary expectations with a number that was higher than I thought I might get. My dad would have been shocked at this choice; don’t rock the boat also meant letting your employer determine your worth. 

Why did I make these choices? I just witnessed my dad work until he physically couldn’t, at a job he never really loved. I didn’t want that for myself. 

Ultimately, I got an offer for that job at a salary that was lower than what I asked for but still higher than I expected. I took it. My dad died just a few months later. The new company was more supportive than I could have imagined during my bereavement, and that role presented me with innumerable opportunities to grow in my career.

Since then, I’ve made another major career move, this time a relatively risky move to a start up in a role where I have no formal training or background. I imagine my dad would have been outwardly supportive, but privately, extremely nervous. 

This move wasn’t easy for me to make. It wasn’t like the last time where I was running away from something; this time I was running towards something else. I was truly rocking the boat. Since starting my new role, I’ve had many days where I doubt myself, my skills, or the decision I made. 

When I feel doubt creep in because I rocked the boat, I remember I have life preservers.

I’m willing to learn. I don’t know everything, but I don’t have to. I can find and use resources when I need to learn something new, whether that’s a Google search, a YouTube video, or reaching out to an expert in the field. Even though it’s uncomfortable, I’m willing to get some things wrong for the sake of learning.

I trust my network. I’ve made a lot of genuine connections with great people over the course of my career, and I maintain that network deliberately. I’m confident that I can rely on those who know me and my work ethic if I find myself on the job market, not only as references but potential points of entry to new roles. 

I am in a place financially where I can afford to take a risk. This is a taboo subject unfortunately, and some people might not agree with including it here, but the bottom line is money affords you the freedom to take risks. If you are in a comfortable situation from a financial perspective (this will look different for everyone), it is much easier to justify rocking the boat. 

Since my dad died, I’ve gained a deeper appreciation for the reasons why he felt like he couldn't rock the boat. His family depended on him; he was the breadwinner and the person who took care of everyone. I’ve also learned that just because he didn’t rock the boat doesn’t mean he did things the easy way. Sometimes staying in a situation because you have to is a lot more difficult than finding something new. 

I’ve also gained a deeper appreciation for the advice he used to give me, because I know I wouldn’t have been able to learn to take risks without learning how to make them feel less risky.