Lean In to Navigating Your Career

Lauren Vang
Lean In SF
Published in
4 min readAug 6, 2018

If you ask a friend, a co-worker or a mentor for some career advice, you might hear different responses and answers. If you do a Google search to see what other might be sharing about career management, career change and career growth, you might be more than overwhelmed. Each person you hear from will give you different advice and suggestions based on their own experiences and expertise. You might be told to do A, or B or C…so which one is it? That’s because only you can decide what’s right for you — so how does one go about this?

Being open-minded and willing to learn from others is a useful approach. Last month Lean In San Francisco hosted the women of TaskRabbit to talk more about navigating your career. Laura Moon, TaskRabbit’s VP of Operations moderated the panel discussion with several TaskRabbit women who shared stories, insights, and bits of wisdom from their career twist and turns.

The women leaders of TaskRabbit.

“Whatever you can do, or dream you can do, begin it. Boldness has genius, power, and magic in it.”- William H. Murray

To set the stage for the panel discussion, Laura shared a longer version of the above quote to kick us off. She then spoke more about her own non-linear career path. She had worked in marketing, gone to business school (Stanford), moved onto product management and now she is currently running TaskRabbit’s operations. There had been times when Laura was asked to take on roles she had no prior experience in and questioned whether taking this route was the best decision. To some of us, the fear of failure is enough for us to stay put in our comfort zone. But after reading Sheryl Sandberg’s book, Lean In: Women, Work, and the Will to Lead, Laura’s “lean in” moment was to jump in with two feet into her new role and excel, which she did.

Moving into the panel discussion, with seven women from different departments at TaskRabbit, there are too many amazing stories and women to highlight, so I’ve decided to highlight two themes to hold onto.

Be bold and leap in.

As each woman shared more of their career pivots, it’s clear they’ve embraced a variety of challenge. Even when they didn’t know exactly what was in stored, or were unsure how they’d carry out what they needed to do, many took a leap of faith like Laura did, and took the plunge into unknown or uncertain waters. It was wonderful to hear many of the women also independently referenced the Lean In book as their guide to helping them navigate the tides of their career trajectories. They spoke about different aspects of their careers and the choices they made, from taking on a more junior position with a career change to struggling with self- confidence during the job search and taking a new role for the wrong reasons (then course correcting it).

But each of them took chances and made hard decisions to get to where they are now. They’ve made not only a difference in their careers, but some of the women have greatly impacted the companies they worked for. Looking back, those challenges have been some of the best lessons for their professional growth. It’s what’s help lead them to be who they are today in their professional lives.

Your career — It’s a jungle gym, not a ladder.

Another theme that rose up from the panel and also pulled from the Lean In book, was to look at your career as a “jungle gym” and not a “ladder”. Remember, in grammar school at recess when you and your friends would climb to the top of the jungle gym and look out at the how high you were? Well because a jungle gym has an array of horizontal and vertical bars, there are many ways to climb to the top. And so, in today’s world, you should view your career journey in the same way. Many have gone down different paths, up and down, left and right to explore the many ways to achieve their career goals — there is no easy ladder that leads you straight to the top. Your career can be a zigzag line and that’s perfectly okay.

“Life is not a straight line. There are no straight lines in nature.”- Anthony Robbins

Laura Moon (far right) speaking with attendees from the event.

Even if you don’t know yet what the “top” looks like for your jungle gym, as long as you’re stimulated and continuously learning in your current role, you’re making progress. Just make sure to keep tabs on it, maximize your learnings by raising your hand for every opportunity and ask for help when you need it. It’s when you no longer have those options that you should consider making a move, whether it’s to a new role, new department or new organization.

As previously mentioned, only you can decide what steps are right for your career, but hopefully, some of the insights from the women of TaskRabbit will resonate with you, inspire you or shed some additional light for you. And if you want to work with a bunch of smart people who is changing the future of work, the TaskRabbit team is hiring.

To maximize your Lean In SF experience, join us in person for our events so you can connect directly with our speakers and be part of the discussions.

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