From overcoming unseen barriers to lifting others as you climb, these women share the best, but most unexpected, career advice they’ve received.
Rising to the executive ranks of any organization takes a combination of skill, grit and luck. Leading as a successful woman takes additional perseverance, as women often have to navigate biases and balance expectations between likability and leadership that male leaders typically don’t.
While there’s no one silver bullet to success, eight Seattle-area female trailblazers have shared the best, but most unexpected, career advice they’ve received.
Know when to leave
“Milk sours when it is past its due date; so too with executives. I left one of my best executive jobs when emotionally, I still wanted to stay, but logically, I knew my work was complete and it was time to hand over the baton to my successor. I never want to exceed that all-important ‘sell by’ date.” —Deanna Oppenheimer, founder, CameoWorks
Don’t wear a sweater around your waist
“I was once told by a senior executive at my first job that I should not wear a sweater tied around my waist. I thought the comment was odd. The executive took me for lunch at a very fancy place and fully elaborated. The person said that expectations for me will be different than expectation for my white or male colleagues. While other people at my then-firm also occasionally wore sweaters tied around their waists (usually the younger generation), the executive pointed out that it was unacceptable for me.
“The executive even used an example of a white woman in the firm who was much like myself in dress. This woman was adored and respected at the firm. The executive noted that people would not afford me the same level of admiration and respect.
“I was 22 years old and the advice was jarring. I felt singled out and it felt very unfair. I thought, ‘Why would anyone treat me differently from my peers and more importantly, why would anyone treat me differently because of the way I dressed, so long as I adhered to office norms?’
“What this person was actually saying was that expectations for me in the workplace would be different. The sweater was a mere example of the fact that I would always need to present an extremely professional demeanor (to have a fighting chance of being taken seriously) and that I would always have to be ‘on my game’ — extra prepared, capable and willing to speak up to be heard. These things would not guarantee equal treatment, but they increased the odds that I would be recognized and that I could have career progression.
“The advice did not feel good at the time. However, it was spot on and incredibly useful. I never forgot it.” —DeShay McCluskey, managing partner, AltraVue Capital
Failing is progress, too
“The most unexpected career advice I received was that failing is progress. From my experience, sometimes women tend to be more risk-averse in a corporate setting. I believe you have to take risks, calculated and educated, but without fear of failing — fail fast and forward. Some of the best career moves I’ve made have been by coloring outside the lines, taking a risk, and pushing for your initiative without fear of the outcome. Whether the risk is successful or fails, you always learn something that you can take forward and apply.
“Challenge yourself to defy convention, be innovative and embrace your inner curiosity.” —Lori Twomey, chief merchant, Zulily
Don’t be so tied to an outcome
“Someone once told me, ‘Don’t be so tied to an outcome’ when I was discussing a problem I was trying to solve at work, and the outcome I wanted to achieve. The advice seemed counterintuitive at the time — I had a great solution in mind and the challenge was just making it happen, right?
“Actually, no. Problem-solving is about being curious and open to new ideas. That’s when the magic happens, and you can end up with an outcome you never imagined.
“I think of this advice all the time, and particularly when navigating my own career. Focusing narrowly on one particular vision of success or title or promotion can close us off to some of the most interesting opportunities to come our way.” —Amy Bohutinsky, chief operating officer, Zillow Group
Be prepared to make trade-offs
“Every decision has trade-offs. That’s reality. Don’t do anything that you’re not totally passionate about. Life is too short.” —Barbara Gordon, vice president of the Habitat for Humanity Seattle-King County board of directors
Continue paying it forward
“In the business/corporate world where many subscribe to Darwinian principles of competition, ‘pay it forward’ may sound trite, even naive. But when I’m feeling great, supporting others’ success gives me even more joy and fulfilment. When I need an extra boost myself, I continue to give where I can and want to. Paying it forward reminds me of first, the allies who support and advocate for me, and second, the positive impact and influence I get to have, no matter the challenges I may be facing.” —Olive Goh, director, Citi Private Bank
Ask 20 people to coffee
“I meet with a lot of talented young people early on in their careers who are wanting to find their path. When I was in my mid-20s, someone gave me the following advice: Whenever you find yourself at a career inflection point, find a way to save up $150 and take out to coffee 20 people who are doing work you find interesting. Don’t be bashful about who you ask or how established or successful they are. Just ask ’em.
“I remember it blowing my mind, at the time, when a local tech exec told me that the majority of the most exciting jobs out there are never posted on those job listing services or company websites. They come from networking serendipity, connecting at the right time with the right person who is working on something you find intrinsically fascinating or rewarding.
“The past few steps I have taken in my career I owe in many ways to this advice, and call several of those then ‘coffee meetings’ [invitees] my colleagues, friends and partners today.” —Julie Sandler, managing director, Pioneer Square Labs
Trust, but follow up
“Trust first, but always verify before making a key decision that impacts others.” —Maria Chavez Wilcox, chief executive officer, YWCA Seattle King Snohomish