Taking an Analytical Approach to Business Coaching

Lindsay Gordon started her career as a bio-engineer because she loved math and science and using her hands to build things. She even has a patent for a medical device that she created. From there she moved on to work in technical support at Google — which, unlike most human beings on the planet, she loves. Not because she likes dealing with stressed out people but because she loves the “treasure hunt” of finding the answers for them. Lindsay eventually started working with new hires at Google and found an affinity for coaching. She started her new career as a side hustle and then eventually launched A Life of Options full-time four years ago. But because of her engineering background, she has a very unique approach to career counseling.

We spoke about her coaching style in our recent interview for the Passionistas Project Podcast. Here are some excerpts.

Passionistas: What's the one thing you're most passionate about?

Lindsay: I am most passionate about designing and creating content, frameworks, and experiences that inspire people to have the courage to take action and do what matters to them in their career. Because I feel like I'm on a mission to relieve the amount of pressure and anxiety we feel about our careers and help people stop doing what they think is right in their career and actually start doing what's right for them.

Passionistas: What led you to the place where that was what you wanted to do?

Lindsay: I think it was the experience that I had while working at Google, which is a fantastic place to work in many ways and also wasn't the right fit for me. I found that the messages that I was getting was, “Well this is the best place in the world to work and, of course, you should want this, that and the other out of your job.” And there wasn't any space for me to feel like it was okay to make my own decision that maybe it wasn't the right fit for me. And so I want to help spread that message that we can choose what works for us. And the thing that works for somebody else is not going to be the thing that works for us. And so really giving people that agency to make that decision for themselves, even though we get a lot of pressure these days about what work should mean to us, where we should want to work, all those types of things.

Passionistas: Talk a little bit about the approach you take to working with a client through your company.

Lindsay: I'm quite unique in this space in that most career coaches come from a background of hiring and recruiting. But given that I have this engineering background, I think of the work that I do as I am applying my engineering brain to this question of “how do we even know what we're looking for in a job that's a good fit for us, and how do we do that in the most practical and structured way?” So I've designed a three-month process that I take people through that gets them clear about what they're looking for. We look at what's important to them in life and how does work fit into that? What's their philosophy of work? What are their values? What are their beliefs about what a successful life looks like? And then we start to look at, okay, let's understand your current role and how that actually fits in with what we're learning about you.

Because a lot of people come to me and they are frustrated, they're stuck, they're aimless, they are convinced they need to quit, they're dissatisfied with where they are and they feel like they should have been further along in their career. And what's interesting is that when I take people through this process of learning all about themselves so that they can make decisions that feel good to them, more than 50% of them don't end up quitting. And it's not that everybody completely falls back in love with their job, which does happen, but people get to see their job a little bit differently. And we take away that like, “Oh my gosh, my only option is to quit.” They can see, “Okay, even though this is maybe not the right fit for me long-term, I understand what I'm getting for from it right now.”

And I can start to work towards what that next step might be. Whether that's an internal transfer, whether that's moving to a new company, whether that's moving to a new field.

Passionistas: Of the people that do make a major change, do you find that there's a common thing that has been holding them back from doing that?

Lindsay: I would probably say there are two aspects. One is not being really clear for themselves about what their strengths are. I think oftentimes when we have strengths, we think of them as, “Oh, but that's the easy thing that I do. Doesn't everybody do that?” Or “Oh, well that's just how my brain works.” And so when people don't see those things as strengths, then they wouldn't even think to pursue something in that direction.

And then I think the other thing is not letting yourself make that choice because of the pressure. There's always pressure from society, from family. One quick example I'll give there is that I worked with somebody who works in project management and she said, “Oh yeah, I've always had a lifelong dream of doing art for video games. But that was never something that my parents allowed me to do. That was an approved thing to study.” And so she's studying engineering, she's been working in project management and once we discovered that, it was like, well let's finally explore this if you've been waiting your whole life and thinking about that in the back of your mind. So she started taking small steps towards that. Creating a portfolio, starting to work with a mentor, exploring what additional schooling would look like. And then over the course of testing it out over a year, she contacted me recently and was like, Lindsay, I have signed up for two year MFA. I cannot even believe that I am doing this thing. I thought I would do this.

Passionistas: What do you think is the most important steps people need to take when they're thinking about making a career change?

Lindsay: I think the first is identifying the pressure that you feel and just starting to be clear about that because if you can't separate what you actually need and what your desires are from the messages that you are getting from other people, that's going to make it really difficult for you to assess if this is the right move for you. So I've always helped people, let's identify and relieve some of that pressure. And then I think the second step is to start to learn as much as you can about what is working and what is not working.

Because oftentimes we get really hyper-focused on the downsides and if we can zoom out a little bit and really look more broadly and understand, if I know what my strengths are, then I can understand how well is this job that I'm doing currently in line with those strengths. If I understand a lot about the type of environment that I like to work in, then I can start to understand, it makes total sense why this particular thing is not a good fit for me because it doesn't match up with the environment. So I really advocate for learning as much as you can about what works for you so that you can accurately assess how the current job you have is matching up to those things

Passionistas: What do you wish women knew?

Lindsay: It's okay to do what's right for you, I think is my simple message across my business. I have a controversial message that it's okay to have a boring job if it works for you. And I think we need more messages like that where actually we get to choose, identify what's right for you and then do that.

The more that women can feel like it is okay for them to identify what works for them, even if it feels controversial, even if it's against the messages that they're getting from society and from their family, I would just be happy if that is part of my legacy of getting women to, to feel like they have agency and can make the choices that feel good to them.

Listen to Lindsay’s full episode here.