In this testimonial interview, product professional Tyler Nichols recounts his career plateau, the emotional toll of layoffs, and his decision to quit and start a business before seeking new employment. He describes hidden psychological barriers, including feeling his Teach for America background was a liability and undervaluing himself as an expense in corporate settings. Tyler struggled with over‑analyzing his resume and LinkedIn, fearing they weren’t compelling enough, until Lynne Levy’s coaching program provided targeted resume/LinkedIn support that clarified his narrative and generated interview opportunities. He then realized interview performance was critical, learning to craft strong first‑minute impressions and memorable closing remarks. Faced with family responsibilities, Tyler weighed the cost of the coaching program against the time it would take to self‑solve, concluding that the financial investment would accelerate his career and yield a higher return. He concludes with a Steve Jobs‑inspired “connect the dots” analogy, emphasizing that his unique combination of experiences forms a distinctive story that, when articulated well, makes him an unstoppable candidate, ultimately leading to a director‑level promotion.
Chapters
Today, where I work, it is amazing because what they need most from me is what I do best. Sometimes I feel a little guilty that I'm not working harder because I'm good at this stuff and I'm passionate about it. And if I ever need to put in longer hours, like, I don't really mind because it's the sort of stuff I love to do, right?
Where you were at before you came into the program? What was kind of going on in your life?
So, uh, it was, it was a long journey. Um, I, uh, have been doing product for a long time, um, but I, I definitely felt like I wasn't progressing the way that I wanted to progress. Um, I wasn't getting promotions. I, it just felt like what I was offering no one wanted, uh, and that was really rough. Um, so I, uh, Eventually decided to quit my job and, and start a business from the ground up, and I was doing that for a while, and then I started looking for work, and it was a very, very hard process. I mean, this was a while back now, and just people were getting laid off like crazy. No one was hiring. It was just a very mentally exhausting sort of thing. And you, you know, you lose a lot of confidence in yourself in those sorts of situations. And so it was kind of tough and that's kind of what led me to want to look for a program kind of like this.
What changed for you and how that affected you landing a job?
I think there were a number of things that I just had no idea was going on inside my head. One was I've got a background in education. I did Teach for America out in Massachusetts. And it was an awesome experience. But right after that, when I started getting into tech really deeply, it started feeling like that was something that was being used against me. That, that was one of the reasons why I wasn't being seen as a leader, or that I wasn't— because I didn't have the perhaps the consulting background or whatever. And, and so I started inadvertently and subconsciously sort of hiding that part of me. I started showing that less and less because I felt like that would inhibit my ability to, to grow. Also, admittedly, right, like, I learned very quickly that, you know, in corporate America, you're often seen as an expense, right? You're— and people want to keep expenses low. And so I just thought that I was worth so much less than I was actually worth, and that I've proven that I am. I'm actually worth, right? And, and so like those were two really, really big things that were in my head that I didn't even realize were holding me back, but, but they really were in a very big way.
Talk to me a little bit about you were really overthinking your resume and your LinkedIn.
I think it was, you know, in my mind it was easier years ago when you could just like go somewhere face to face and show them, you know, yourself and, uh, and And, you know, it felt more personable and real, right? Today, one of the things that's just so complicated is you submit everything online. No one sees your face. And so I don't even know if people are reading my resume. I don't know if people are looking at my LinkedIn and thinking that it's, you know, a bunch of crap. I, like, I was overanalyzing like crazy and it was very frustrating and difficult, right? And when you overanalyze that stuff, You start wondering, uh, is it my content? Is the stuff that I've been doing, is that the problem? I'm not doing cool enough stuff, or is it just that I'm not like putting the sales spin on it? Right. Um, and that part is like really kind of obnoxious, uh, trying to figure out the difference there. And I couldn't, couldn't quite figure it out. Um, and so one thing that I really loved is, you know, in this program, Lynne's got, uh, team members that focus specifically on your resume and your LinkedIn and, um, and make sure that your digital presence is spot on. And what was really great about that is that then I could feel really good about the sales bit, right? Then I could just focus on, can I tell the story that is authentic to me and that I think would resonate with the, uh, the place I'm applying for? Um, it just really simplified a lot. And so I didn't have to worry about that. And honestly, when, when I got that set up I started getting interviews coming in, I could focus on the interview part, which is, it's the bigger piece anyway. And I think that was a huge win, huge help for me.
So talk a little bit about first impressions being really important and how this really helped you in the interview process as well.
So I love products. I'm a product guy. And in the beginning of my journey of trying to find a job, I was— the way I thought was interviewing is a whole skill set that I don't really care to get good at. I really don't. I want to be a product guy, right? And so I want to focus on that. And my, my thought is, you know, I'll just be really good at my product stuff and then someone will notice and then I'll get the job and it'll be fine and I won't ever have to learn that skill. The reality of it is That you can't, you can't think that way. I mean, I found zero success that way. And so I had to shift my focus and think, okay, as much as I don't want to do this, I want to become the master at interviews. Um, and then I can get the job and then I can focus on product and do all that sort of thing. Um, and so, so to your point earlier, um, I, what I found with my answers and I think which is what's most common is when someone asks you a question, As a response, you typically start pretty blah, right? You're trying to figure out what am I trying to say, and then you pick up steam and you feel pretty comfortable and confident, and then you get to the end of your answer and you're like, I don't know how to end this, and so I'm just gonna do it kind of blah again and go out, right? Um, but the ironic thing is that's so common, but that is exactly opposite of what the interviewers want to see. Right? Interviewers are going to be hugely skewed by the first impression and the last thing they remember, which means I was doing it completely backwards. And so I started thinking, how can I make sure that that first 30 seconds, the first minute are spot on and that people are like, dude, I love this guy. And then at the end, I can leave some sort of like zinger or thought-provoking thing on the back. So that way they can, when they think back to interviewing me, they can be like, oh yeah, it was that guy. He was awesome.
How did you get to the point where you could make that decision of, you know what, I also know I have to invest in myself?
Yeah, it's, it's a very stressful thing. I, you know, I had two kids at the time and my wife was pregnant with number three as I was trying to find a job. And it was, was really hard. And obviously, like, it can be emotionally draining too, right? Because like, I want to protect my family and I want to support my wife, especially when she's bearing our children. And so I know that I'm a really sharp guy. I know that eventually I could have figured it out. But what I realized was it would be really nice to have some way to move faster. Right. And so the way that I saw it was spending money was better than spending time. I would rather spend an amount of money as opposed to 6 months, a year, 18 months, you know, I, I didn't want to spend that. That was more expensive to me, uh, than, than the dollars. Um, and so I, I just realized I, I want to do this. And, and the other thing, sort of logically speaking, is, um, I knew that if I could make more money than I could, um, uh, like by, by joining a course, uh, getting mentorship, if I could make more money than the cost of the course itself then it would be a no-brainer, right? And so I started looking through it, uh, with that lens too and started trying to find ways and different, you know, researching different programs to see what, what could be the best fit for me. Um, and, uh, and ultimately I decided that, you know, like this, this does make sense to make this investment even though it's so hard because I think that it will get me to where I need to go faster.
You gave a really good analogy when we talked last about Steve Jobs. And connecting the dots. So would you tell everybody kind of what that means to you?
I think, you know, at the end of the day, having your dream job is so much better than just having any old job. And, you know, there's a lot of reasons for that. And so how do you find that dream job, right? I was impressed. Steve Jobs gave a commencement speech a number of years ago before he passed. And he talked about how his journey included, you know, he dropped out of college and he went to calligraphy class and he loved, you know, how to write things and he loved technology and all these different things. And he made the comment that every single person has a unique set of dots. There is going to be no one else out there that has the exact same formation of dots. As you have. And so if you know how to connect your dots in a very meaningful way and then sell it to other people, then you become unstoppable, right? Because no one's going to be better at that dot formation than you. And so then it becomes super easy. You're not competing against a million other product managers. You're competing against literally zero other people. There's only one Tyler Nichols, and I'm me, and I'm here in this interview right now. And you can hire me if you want.
