Lindsay Gordon Takes an Analytical Approach to Business Coaching

In 2014, Lindsay Gordon hit career dissatisfaction rock bottom at her job at Google. She started doing any exercise she could find, that would help her reflect on what was important to her and what she needed out of a job. She wanted to share the results of her research with others, so she founded A Life of Options. As a career coach, she works with analytically-minded people who are feeling uninspired or crushed by an ill-fitting job.

Learn more about Lindsay.

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FULL TRANSCRIPT: 

Passionistas: Hi and welcome to the Passionistas Project Podcast. We're Amy and Nancy Harrington and today we're talking with Lindsay Gordon. In 2014, Lindsay hit career dissatisfaction, rock bottom. She started doing any exercise she could find that would help her reflect on what was important to her and what she needed out of a job. She wanted to share the results of her research with others. So she founded A Life of Options. As a career coach, she works with analytically-minded people who are feeling uninspired or crushed by an ill-fitting job. So please welcome to the show Lindsay Gordon.

Lindsay: Thank you so much. Happy to be here.

Passionistas: Thanks for joining us. So Lindsay, 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. Cause 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: So 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. And 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: So now let's go back a little bit. You actually studied bioengineering in college?

Lindsay: I did, yes.

Passionistas: Why did you take that path and where did that lead you in the beginning?

Lindsay: Yeah, I always had been interested in math and science very early on and I loved getting to work with my hands and build things. And so engineering seemed like a pretty good fit for me. And I went to a fascinating tiny, tiny engineering school outside of Boston, only 75 people per class. That's how tiny it was. And it was all about building and design and getting to really understand your user, connect with people and all kinds of fascinating things. So I thought, okay, engineering is great. I also like biology. We'll combine those two. And I got to work on um, some medical devices with Boston scientific. I actually have a patent for a medical device. And so that was kind of where I landed in college. And engineering has always been interesting to me. I kind of feel like it's a nice combination of people, but then also that hands on design and creation work.

Passionistas: Were you doing that kind of work at Google? What were you doing there?

Lindsay: I somehow am on my third career already. So I started off in engineering, did that for a little bit and then kind of fell into doing technical support at Google. And I am one of probably a unique kind of human that actually loves technical support. I love it. I love it. I love it. I love customer service. Um, it's kind of the, again, that combination of getting to connect with people, but also having this treasure hunt. Every time somebody calls you and you know, they say, I have this particular problem and you need to figure out what are the right types of questions to ask them, what are the right troubleshooting steps to take. So I just absolutely love to getting to do. And I did about five years of technical support there.

Passionistas: So you talked a little bit already about the atmosphere at Google, but tell us like specifically what it was like working there and you said, you know, you were supposed to like it but you didn't. So tell us a little bit more about that.

Lindsay: I'm so grateful for so many things about Google. I got to meet incredible people. They have fantastic programs to bring interesting speakers in. I got to learn so much. I got to do a lot of facilitation at Google, which was great. And um, it just, it was a very big place, right? It's a big company now and there is bureaucracy and it's hard to move around. I really wanted to move to the more people side of the business after I had done many years in technical support and I found that a really difficult thing to do.

And um, I also, because I loved customer service and I love designing, as I mentioned, I love designing frameworks and um, exercises and all this kind of stuff. And on the team that I was on, it was a little bit more about metrics, you know, like are you the biggest case closer, um, you know, metrics in the direction of customer service. But I also cared about the people on our team and the people side of that. And so I was always trying to do, um, some other projects and it just felt like I was more expected to do more of the metrics around technical support. So I think I wanted a little bit more creativity, a little bit more ease of moving around. Maybe I would have thrived at a smaller company. And so those were a couple of the pieces that I was feeling that just didn't seem like quite the right fit for me.

Passionistas: So did you leave there knowing what you were going to do next or did you start to think about what your next move was going to be while you were still working there?

Lindsay: I completely fell into running my own business. Like all good career transitions. I did not know that this was in the cards at all. So while at Google, because I had so many of these other interests that I wanted to be cultivating, I started working on our onboarding and training for new hires. And as I was talking to our new hires, everyone was really stressed about, Oh my gosh, I'm new here. You know, how do I have conversations with my manager? What if I'm stuck in technical support for the rest of time? And so I just started talking to people about their job and how, how to think about it and kind of relieving some of that anxiety. And a lot of people said to me, you would be a great coach now, I had no idea what that meant at the time. So enough people had mentioned that.

So I said, okay, I really need to test out what this thing is. I need to go learn about it. So I took one class at San Francisco state about learning coaching tools and I was amazed because I didn't actually know that there were skills that you could learn that I was already trying to do innately. So I kind of accidentally signed myself up for this year and a half long certificate. Loved it. And as I said, my goal was to move over to a more people focused role at Google. So while I was trying to figure that out, people started coming to me and saying, are you taking clients? I have people to refer to you. And I was like, Whoa, Whoa, Whoa. Everybody. Like I'm, I'm not doing my own business, you know, these are my plans. But luckily I said yes and kind of ran it as what I like to call my accidental side business and ran it for about a year while I was still at Google.

I'm a very risk averse person and one thing that I talked to clients a lot about is test out anything that you think might be the right next step for you. So I tested it out by running it on the side for a year as a part time thing. I also tested it out by eventually moving into a career development role at Google so that I can test out do I enjoy doing this? You know, is it something that I find fulfilling? Are people finding it useful? So after about this year of running it on the side, I thought, you know what, it might be time to try this full time and to really go all in and see what it's like to run your own business. And that was about three and a half years ago now.

Passionistas: And the perfect example to the people that you're helping, you know, you're practicing what you preach.

Lindsay: And a lot of times I think we talk about entrepreneurship as something that is very risky and um, read an interesting book recently, I think it was the um, side hustle book. I can't remember the exact title, but they talk about how actually entrepreneurs tend to be very risk averse and if you're doing it properly, you're trying to de risk every avenue possible in order to have the greatest success in doing your own thing. So I like kind of sharing that message to have, it doesn't need to be just, I'm going to quit anything. Everything without having any idea whether I like it. I haven't tested anything out. Actually, there are many ways to de-risk the process so that you can feel really good about running your own thing, if that's the right thing for you.

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

Lindsay: So 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 kind of 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. So we look at, you know, 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, it's not that they, 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. And so 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. I had a client who came to me and she was like, I need to quit. I'm done with this job. I might even be done with this field. Like I don't know that this is what I want anymore. Two sessions in, we did a couple of exercises and she kind of like laughed and was like, actually I job is a great fit for me for all of these particular reasons. I was hyper focused on the downsides and actually if I make these two changes, um, I'm really grateful for where I am and this is actually a great fit for me. So I think the, the mindset piece is such a big piece. Sometimes nothing about the external situation has to change for you to have a different experience of your work.

Passionistas: And of the people that do make a major change, do you find that there's like 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 you know, 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. So for example, I had a woman who was working in engineering who, uh, wanted to move to something else, was unhappy there, and she had never thought of teaching as a big strength of hers, but it kept coming up over and over again in these exercises. So she ended up moving internally to another fantastic job that was more teaching the engineering, um, discipline. And so she's over the moon, but just had never considered that before.

And then I think the other thing is not letting yourself make that choice because of the pressure, right? 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 a, uh, an approved, you know, thing to study. And so she's studying engineering, she's been working in project management and you know, once we discovered that, it was like, okay, 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, right? Creating a portfolio, starting to work with a mentor, uh, 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, you know, 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 as I mentioned, 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, okay, 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, Oh, 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: We're Amy and Nancy Harrington and you're listening to the Passionistas Project Podcast and our interview with Lindsay Gordon. To learn more about her work as a career coach. Visit ALifeOfOptions.com. Now here's more of our interview with Lindsay.

Passionistas: You're obviously very confident, but do you ever get self-doubt and how do you get past it?

Lindsay: 100% my goodness, I like to say that running a business I have had highs that are way higher than any nine to five I've had and lows that are way lower than any nine to five I've had. So I think it's so common as a business owner to have self-doubt. Um, I remember several times, especially in that first year where I just got rocked by something. You know, it is, it is very personal for the product to be you, right? Everything that I've created comes from my mind. It's my ideas. I'm out there selling myself. And so in the beginning it does feel very personal if people are saying no to you. I remember the first time where I felt like maybe the client wasn't getting exactly what I wanted and you know, really shook my confidence. So it's hard. It still happens. I think that's probably something that never goes away. But I'm better, you know, riding the ebbs and flows.

One thing that I have really appreciated and that has helped with confidence is collecting a group of fantastic women who are also running their business. And we meet virtually once a month and just check in, you know, who feels like their business is broken today. You know, who, um, has some great things to celebrate who has some questions, who's struggling with the time of year that we're in and the low volume of clients or whatever it is. But really just being able to share and not feel like I am alone in my house doing this thing by myself. So that's been huge for me.

Passionistas: What's your best habit?

Lindsay: I think my best habit is reaching out to people. So for whatever reason I have been graced with kind of the excitement and willingness to just reach out to anyone that I find interesting or anyone that I connect with and to see how I might be able to help them. How am I be able to learn about their business? Who I might know that I can connect to? So this group of women that I've created, I think it's probably 30 or 40 women at this point, and it's really just anyone who I come across, I could see your name in a newsletter, I could, you know, hear about you from a friend and I'll reach out. And if I think you're fantastic and I want you in kind of my circle of entrepreneurs, I will invite you to this group and to collaborate on workshops with me.

So I think kind of that feeling of connection and building the community that I want has always been something that comes really easily to me. So kind of explain it as I aggressively friend people, but I think I get to meet a lot of interesting people that way and people actually respond really positively to somebody reaching out and saying, Hey, I think you're fantastic. I would love to hear more about what you're up to and how I might support you.

And I actually, when I first started running the business full time, I did not think I was going to like it because of how lonely it was. I am already an introvert and so I'm at risk of, you know, not leaving my house for four days if I'm just working at home by myself. And so because I knew that was something that I was worried about, I really made an intentional effort to build a community. And that's something I help clients do too. If you're worried about anything, like, I don't know if this career is going to be a good fit for me for this, that and the other reason. That's so helpful because then we get to design around that. We get to take intentional action to figure that out, so I definitely knew that that was something I was going to struggle with and I needed to work hard at it to make sure I enjoyed running my own business.

Passionistas: Is there a lesson that you've learned so far on your journey that really sticks with you?

Lindsay: I think the lesson that we get to change our mind, we get to change our career. We get to try new things and it is never too late. I hear the message a lot that, well, I studied this in college. I'm not using my degree. Well, I've already been in this area for so many years and I just, I don't want people to feel that way. I want people to feel like their career is a long and varied path. Who knows how it's going to go. There's going to be a lot of serendipity be open to falling into things.

I think for me, you know, engineering to customer service to running your own business as a career coach makes no logical sense if you were to explain it in that way. And I think people get really wrapped up in, you know, well it looks really chaotic, the things that I've done, but there's a way in which I can tell my story where it has always been about listening to people, understanding their challenges, building frameworks and experiences for them to inspire them to take action. And that's been true across engineering, technical support and career coaching. And so I want people to feel like there's more playfulness and fun and curiosity and serendipity that goes along with career rather than feeling like I have to do this one thing because that's where I landed.

Passionistas: Do you think there's a personality trait that you possess that's helped you succeed?

Lindsay: I think curiosity is probably one of the biggest things that is just constantly running for me. And I'm curious. So I was curious about the onboarding of new hire experience and started talking to them. Somebody mentioned a coach. I was really curious about that. And so I think I love following that curiosity and learning about these interesting opportunities that I hear about and it really opens up a lot of doors. If you follow your curiosity.

Passionistas: What's been the most rewarding part of your career?

Lindsay: As a business owner, I have never felt more creative and impactful. I get to design things and come up with ideas as often as I want. Designing programs, designing workshops, designing exercises for people. I absolutely love that part of it. And then as far as impact, it's an incredible feeling to know that every result that I get, I made that happen through my courage, through my creativity, through my gifts, through my actions, through my requests. And so it's a very direct, I put effort in and I get results. And so it's very exciting to me to be able to feel those two pieces every day. And I think that's my favorite part of being able to run my own thing.

Passionistas: And have you had professional mentors?

Lindsay: Yes. That word always feels so big to me if like, Oh my gosh, do I have an official mentor? Yes, of course. I have had people who have been so thoughtful throughout my career. One that comes to mind is my most recent manager at Google who has been a fantastic support for me and has believed in my business probably before I even did. So he's been fantastic. There are also people who, one person that comes to mind, you know, I, she was a woman who had been running her business for a little bit longer than I had and when I started running my business and have this reaching out thing that I do, I reached out to a lot of other women and said, I would love to learn from you, you know, learn about how your business is going and see if there are ways that I can support you. And one of the things that she did is she said, Oh, I referred you to this other person, but I told them that your rates were higher than they are because you're actually charging too little.

And you know, even moments like that, I consider that to be such a gift. And you know, a moment of mentorship where somebody who was a little bit further along than me was able to support me and you know, teach me something that I didn't know. So I'm always looking for those opportunities to, to be able to do that to another woman who's just starting a business of like, Oh, you're undercharging yourself. Great. I'm going to send you to somebody and tell them that you, your rates are higher. So things like that, there've been so many people along the way, especially in building a business that have been so supportive. And I think we sometimes hear this question of why don't women support women? And from my personal experience, I have not found that to be true at all. I have found the most supportive women who are running their businesses, who are all about let's help each other so that we can all thrive. So I've been really happy to see that be the case and I want to help continue, you know, being somebody who supports others.

Passionistas: Do you have a mantra that you live by?

Lindsay: One of the ones that always sticks in my head is the proverb around the best time to plant a tree was 20 years ago. The next best time is now. Um, and another one that I use in business that comes from one of my, another one of my business mentor is a business coach. Um, that has been fantastic to work with is it's not a question of if it's a question of when. And so as I go about my business and as I think about the impact that I want to make, it's not a question of if I will make that impact, it's a question of when I will make that impact.

Passionistas: What's your definition of success?

Lindsay: Making choice of the feel good to you? I think doing the things that are important to you, living in line with your own values and for me having some sort of positive impact as well. So I, I, I want to lead a great life that does something great for the world that has an impact on other people. And success is, you know, doing that in line with the way that I want to live life.

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, 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, you know, identify what's right for you and then do that.

I have a, one of my most earliest clients had a really high paying lawyer job and everyone around her in her community was saying, um, you're being under-utilized. This job was not challenging enough. You should get out of there and be doing something more. And so she came to me and was like, yeah, I'm being kind of under-utilized at my job and I'm being well paid. So I don't really know how to think about this. And once we started discovering what was most important to her, she found that providing financial support for her then young son was the most important thing for her. And so she was able to make this really confident decision that actually this job gives me exactly what I need right now. It pays me really well. It allows me to provide that financial stability and I actually have extra mental energy and time to be able to go and spend it with my son.

And so to see her make that decision, even though everyone around her was saying, you should be challenged more or you should be utilized more, you know, was such a powerful moment. So 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, you know, 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.

Passionistas: What's your dream for yourself?

Lindsay: To live life courageously, to always be taking action and having an impact in the world and being able to follow my interests. I just want to lead a courageous, exciting, adventurous life that hopefully inspires other people to do the same with the things that are important to them.

Passionistas: Thanks for listening to the Passionistas Project Podcast and our interview with Lindsay Gordon. To learn more about her work as a career coach, visit ALifeOfOptions.com. Please visit the PassionistasProject.com to learn more about our podcast and our new subscription box filled with products made by women-owned businesses and female artisans. To inspire you to follow your passions. Sign up for our mailing list to get 10% off your first purchase, and be sure to subscribe to the Passionistas Project Podcast so you don't miss any of our upcoming inspiring guests.