Jennifer Winn: How to Successfully Transition to a ‘Great-Fit’ Career
As many Peak Prosperity readers know, I was on a very different career track before opting out of the corporate race and teaming up with Chris.
I had been dissatisfied for years leading up to this career transition. There were many reasons for this, but at the core, it was because there was a disconnect between the work I was doing and the values I held. As a result, I found myself committing 60+ hours per week to a job that didn't fulfill me, nor that I felt was relevant to the type of future ahead as forecasted by the Crash Course.
To maximize my odds for success in transitioning not just to a new job, but also hopefully to a lifelong "great-fit" career, I spent a lot of time studying the science of career management and engaging with a platoon of professional consultants and executive coaches. Through this research, I learned that there are indeed time-honored practices that can statistically and materially improve your chances for identifying work that matches your aptitudes and passions AND for finding gainful employment in this new field.
Jennifer Winn was one of the expert coaches I worked with and a tremendously helpful guide for me as I put this methodology into practice in my own career transition. The fact that I'm writing this post – for a company I've co-founded, in partnership with a personal hero, doing purposeful work that I love – shows that the process worked out pretty well.
I've detailed out this methodology in a book Peak Prosperity has just published this week titled Finding Your Way to Your Authentic Career. It's written for anyone who thinks that there may be a higher use of their talents than their current job path is offering. It's also a helpful resource for new grads seeking to identify where to place their professional focus, as well as for soon-to-be retirees wondering how to find purpose after their current career ends.
To provide folks with a better sense of the guidance the book offers, I sat down with Jennifer to discuss the essential elements of the transition process. We focus particularly on the most important and earliest stage of the process, in which you develop an enhanced understanding of your core attributes – your interests, your natural aptitudes, your values – and use these foundational building blocks to begin constructing a vision for what fulfillment looks like for you. These insights will serve as the compass points that will guide everything else that you do in your transition process (and will most likely end up adding clarity to other elements of your life outside of work, too).
Click the play button below to listen to my interview with Jennifer Winn (54m:36s):
Listen to the AudioRead the Full Transcript!
Jennifer Winn: How to Successfully Transition to a ‘Great-Fit’ Career
The following is a transcript of recorded content. Please note, these transcripts are not always perfect and may contain typos. If you notice any major mistakes, please feel free to report them by opening a Technical Support ticket under the Help menu at the top of the screen.
Adam Taggart: Hello, and welcome to this Resilient Life podcast. Resilient Life is part of PeakProsperity.com; it is where we focus on practicable and actionable knowledge for building a better future. I am your host, Adam Taggart, and today’s guest is Jennifer Winn, founder of Winn Performance Partners and Executive Consulting and Coaching Boutique Firm.
I have invited Jennifer on the program to talk about career transition. Recent surveys show that most Americans are dissatisfied with their current jobs and 60% would chose a different career if they could. This desire to change careers is something Chris and I hear often from Peak Prosperity readers, who, in addition to the general job malaise most workers feel, have the additional concern of feeling their expertise and skills may be less relevant in a future impacted by Peak Oil, or that their industries are at high-risk form the slowed to no economic forecasted by the Crash Course.
While many yearn for a new career, what they are really seeking is more fulfilling work, work with purpose and meaning, which is a very important part of the personal resiliency we advocate developing here at Peak Prosperity. Unfortunately, many of those yearning never actually take the steps to transition, as the process seems too daunting or too costly from a time or money standpoint. But there is a methodical process to find your professional purpose – your authentic career, as I call it – and to transition over to it.
We are going to discuss that today with Jennifer. How can Adam be so certain this process works? you might be thinking. Because I followed it to make my one transition from dissatisfied Silicon Valley executive to fulfilled Co-Founder of PeakProsperity.com, and Jennifer was an instrumental resource to me along that process, which is why I am so excited to have here join me today.
Jennifer Winn: Thank you, Adam. It is a pleasure to be here.
Adam Taggart: Let us start by giving our listeners a quick description of your expertise in career management. Do you mind just giving us a little background?
Jennifer Winn: Sure. I do executive consulting and coaching work. The bulk of that is with companies that hire me directly to work senior executives, typically Director-level and above, on leadership, interpersonal dynamics and communication. A big piece of what I do is working with individuals on understanding what they are best suited for so that they are able to find a career that is very fulfilling to them and that meets their needs over the long term.
Adam Taggart: Great. As I mentioned earlier on, we are going to talk about career transition. In addition to being a big catalyst in my journey, you also went through a big career transition yourself, years ago. That is true, right?
Jennifer Winn: Yes, absolutely.
Adam Taggart: Before we start talking at a higher level for everybody listening, just tell us a little bit about the transition you went through.
Jennifer Winn: I have actually done several major career transitions in my lifetime, and it is partly why when I work with folks, I say I really have been in your shoes. I know what this is like and I know how daunting it can be.
I started out in theater, I was a performer and I did theater, singing, and things like that. I grew up in the Midwest and I moved to New York, in the classic here I am in New York City, ready to do theater. I had moderate success in that, and one of the things I learned was that I did not really like the day-to-day life of it, the tremendous uncertainty. You have to pick up and go be in some remote location for weeks or months on end.
At that time, through happenstance more than anything else, through doing temp work, I wound up working in an investment bank and was intrigued by what I saw there. I thought okay, this is really different, and if I can just figure out what they are doing here, I think this is an exciting environment. I worked on a trading floor for a year or a year and a half, something like that, then wound up going to business school, which is what brought me out to California. I went to Stanford.
Then, coming out of business school, I was trying to find a way to blend this creative, artistic side of my personality with this business orientation. I went into advertising and found that was not all that creative and did not pay all that well. So it was not very helpful in paying off all my student loans from going to business school. Then I wound up working for Charles Schwab for several years, about four or five years I was there.
Then eventually, I said, I am not quite there yet, I still have not found that sweet spot and started another transition trying to get more towards what is it that is really motivating to me. I went all the way back looking at why did I get into theater, what was interesting about that. For me what was fascinating about theater was figuring out the puzzle of what would make a character do this, what would make someone say that? Why would they take these actions? It was really the psychology of that that was what was so fascinating. When I applied that to the business world, what that led me to is this area of coaching. What makes one executive more effective or much more successful than another one? So it is many of the same things.
My work now, in an odd way, is quite similar to what it was back when I was in theater, where I spent a lot of time trying to figure out what is it that will make this person come off this way and be successful in this career. In some ways I have come back full circle, but I am very fulfilled in my role now because it is playing on all of these strings. And all of these experiences that I had in my background have come to bear, and they are useful very much in the work that I do now. I draw as much on my theater training as I do on my business school training or my personal experience in a managerial role.
Adam Taggart: I think it is really important for people to understand that as we go into this conversation we are about to have, it is not just an academic discussion. I mean, there are a lot of study, skills, and techniques that have been proved out over time about the study of career management. It is heavily informed by the multiple career transitions that you went through. You are not just talking at a theoretical level; you are also talking from a point of actually having put this into practice in your own life.
Jennifer Winn: Absolutely.
Adam Taggart: Let us build on that, because not only do I think you have a very valuable perspective to offer from the expertise you have developed in the career management space and the personal experience that you have had in making transition, but you are also familiar with the Crash Course. You have even attended a private event that Chris keynoted when he was up in northern California last year. You understand the issues that our audience is grappling with. You know that they probably have many of the same concerns that the average person does around career arc and whatnot, but they have this whole other set of concerns on top of it in terms of the macro dynamics that are likely to shape the future.
Since we are going to focus on career transitions today, as I mentioned earlier, I talk to so many people that contact us directly about their dissatisfaction and where they are in their careers, but even when I go to a cocktail party, a social event, I find that if I just ask one or two questions with minimal scratching beneath the surface I can get seven out of ten, eight out of ten people to admit within a couple of sentences that they probably wish they were doing something different for a living. This sense of “life having put you on a path that is probably not your true path” is a very, very common feeling. Yet as I also mentioned earlier, everybody makes the career transition, and for some people that is probably the right thing because it is a pretty big endeavor and it requires a lot of focus and commitment to do well.
I guess before we get started about the process itself, do you have any advice on for those wishing they had taken a different path. Who are the ones who should be considering making a career transition versus just trying to feel better about the path they are currently on?
Jennifer Winn: It is interesting in that usually when people come to me, especially if they are in a job, it is a pretty good job from the outside. It pays well, it fits their training, but it is not their passion, and it is I just feel unhappy or I feel like I am not on the right path. Usually the first thing that I would say to them is, let us look at a dual approach. Let us try to figure out what the optimal path for you is; it may be very, very different. Also, what can you do right now to start to maybe adjust what you are doing, or tweak your work, or maybe get into a little bit different group, or expand your responsibilities in a different direction, to try to make it more palatable to be where you are right now if you are feeling at unrest?
I find that many times what will happen is that if they just can tweak it, sometimes it is amazing what a small adjustment can do to make you feel more comfortable in your work. If we address some of those things that are manageable in their current work, sometimes people say, oh my gosh, I feel so much more comfortable that I am actually okay now. I think I do want to stay here. There may very well be very valuable reasons for not making a big change that have to do with their personal life, what is going on. They may have a new baby at home; they may have elderly parents that they are in the process of trying to transition them to a new home. There are all kinds of life events that might give you good reason to say let us hold off on making a big transition right now. However, having said that, I think there is a tremendous value to at least starting the process about thinking what is the next thing, even if right now is not the best time.
Adam Taggart: I think that is a great point, and we are going to get into this more deeply in just a moment. A huge part of the career transition process is, it all starts with a better sense of self-understanding. Sort of like what you are mentioning in your theater work on what really makes this character tick. Of course, by this character, I mean you. For those for whom considering a career transition may make sense, let us actually move on to the details here. As you know, based in no small part from our work together, I have written a book about the career transition process. What we are going to talk about at a high level, there is a book that is going to be available by the time this podcast is released, on the Peak Prosperity site, that people can take a look at. If this is a topic of interest to them, they will be able to get the book. Within the book, the career transition process is divided into three stages.
Stage 1 is taking control of your professional future. Stage 2 is navigating the fallow period. Stage 3 is making a successful transition. We will talk in a moment specifically about what each one of those stages involves. I would like to focus right now on the first stage, which, in many ways, I feel is the most important one. It is where you set the goals and vision for your career switch.
As we talked about, it is all about developing a better understanding of yourself and then using that understanding to create the requirements for the work you are going to go after that is going to be more fulfilling for you. Once you have these insights, you are empowered to start making decisions and taking directive action. Because this is so important, it is very much like, before you build a house, you spend time with an architect and you actually design the requirements for the house. You actually build a vision and a set of visual plans for the house, and then everybody who is involved in the process uses that to guide their actions.
As we talk about this stage where introspection and self-understanding is really important, these are rough existential questions. Questions like who am I? what do I value? what are my strengths? what fulfills me? Those are very simple questions to ask but they are very, very hard questions to really answer. What effective strategies are out there for coming to a better understanding of ourselves? What tools, techniques, exercises do you find most helpful in enabling someone to answer these questions?
Jennifer Winn: The exercises that I have found particularly helpful – I know in reading your book, which is a wonderful resource, I will give you a plug on that right now. I read the whole thing, and I think it is a terrific, terrific resource for people in making this transition that can feel so daunting. One of my favorite ones that I tell people, just start with this, is a version of this Seven Stories exercise, which is pulled from the Five O’Clock Cookbooks, I believe. The Seven Stories exercise is one where you just analyze your own life and you just start out with 20 different things that you say, throughout my life, what were some things that really absolutely engaging to me? I encourage clients when they do this to go back to when they were in grade school or any time in their life and just say what did you get absorbed in, what did you feel really proud of, what did you love doing? and do not worry about if it is something that is important or a big thing. If it was important to you and you think about it, it makes you feel really positive as you relive that experience, then that is one of your stories.
What happens is, people get so bogged down in expectations that others have for them, or teachers who said, oh, you were really good at math; you should do this. I can remember being told in junior high you should really study math. And I was like, what can I do with that? The response was you can be a math teacher. I thought, I do not want to be a math teacher. These expectations get shoved on to you, and it can be very hard to shake them off. If you go back to things that were really, really energizing and really fun when you were younger, many times the seeds for what is going to be motivating to you in y our new career will surface.
That is where, as a career coach/consultant does this process, it is much easier for me to help people if I can read through all that because I can say oh, I see this kernel here; I see this connection in this. People often do not see it for themselves, so that process of, you boil it down to seven – you start out with more than that, but you get down with seven that you really analyze in detail – you say What was it that was exciting about that? Why did I like it? How did I get involved in it? Was it something I initiated? Did someone suggest it to me? What was my role? What was I acknowledged for, if anything, or was it something that was very private? All of that information can really help inform what is going to be an optimal path for you down the road. I think that is a really, really good resource of just minding your own background and your own experiences.
Adam Taggart: That is a great resource, and I just want to underscore two things that you mentioned there, because I completely agree with what you said. Really, at the core of this process is boiling yourself down to the fundamental building blocks, at least right at the beginning, to really ask yourself – my strengths; my attributes; my passions; my values. What are the core things that make up who I am? Once you understand that, you understand what you are so that you can start looking for opportunities that fit who you are. You understand who you are not, which makes it a lot easier to start saying no to other opportunities that might be available to you, but as you really begin to understand your true nature, you can more clearly realize just are not a good fit for you. In your case, you might have been very skilled at math, but maybe being a math teacher or going down a very quantitative career, even though you could have, would not be the right thing for you.
You also mentioned how we have these expectations hoisted on us. One revelation that was very helpful for me in my transition process, because I still felt pressure as I was leaving my old career and trying to figure out what to do next, was that I still did feel a lot of pressure to keep some of these doors open that everybody in my presence looked at as great opportunities. I knew they were great on paper; I just did not quite know that they were not great for me. Of course, going through this process you are talking about helped me to begin to realize that.
One thing that really helped was, I heard from somebody, from a psychological expert, that as part of the normal human maturation process you are supposed to make a shift in how you live your life – this typically happens around midlife, and it is probably one of the big reasons why people have midlife crises. You are making a shift from living a life based on others expectations of you and beginning to then start living a life based on your own expectations of yourself. I think that is a big part of what we are trying to do here in this career transition process is to say, yes, my parents had expectations for me, my teachers did, my peers have all sorts of interests that they are influencing me with, but really this is what is important to me at my core. It might be consistent with those expectations, or it might be completely different.
I am getting to the point where if it is completely different, I am okay with that. I can then step forward into a path that feels much more true or authentic to me without worrying whether the people may or may not be expecting from me. Would you agree with all that?
Jennifer Winn: I would completely agree with that, Adam. In fact one of the things that I tell people is, be very protective of yourself in who you have around you. It is really hard; sometimes the enemy of this process can be what I call “people who know you too well,” in that it may be family members, it can be longtime friends; they do not mean to do anything to impede your progress, but they do feel like they know you so well. They think they know what is best for you. So it is oh, you would hate that job or why would you want to do that; that is crazy. Or you will never make money doing that. It is all this stuff at a time when you are already really vulnerable. You are just like, oh, no, what am I doing? I am losing my mind.
Adam Taggart: Right.
Jennifer Winn: I am not even sure what I want to do, but it is clearly not the right thing. You do have to really make sure you surround yourself with people who are going to be very open-minded and supportive. Sometimes you do have to take a little break from some good friends and colleagues and just surround yourself with some other folks that are able to see you with fresher eyes because it can be hard.
Also, as you mentioned, when you are leaving a good job, the opportunities that are coming your way tend to be quite similar to your last job. If you are in a job or transitioning out, you get recruiters, calls from friends; they are going to connect you with stuff that is quite similar. If you want to do something different, it is really hard to break free of that. The more you can create space from that, the better. I remember in my case, after I had left Schwab, I was really wanting to do something different and I thought there has to be more on the people side of things, I am not sure what shape that takes. This was 14 or 15 years ago, so the whole executive coaching field was not that known then; it is much more known now. I said I think it is something in this area but I was not sure, it was not crystallized yet.
At that time, I remember getting a call from a company that was in the mapping business. I think eventually it was merged and bought whatever became MapQuest or one of those earlier iterations of the mapping technology. They liked the fact that I had been in advertising before, so they were heavily recruiting me to come in and do marketing for that kind of role. It was hard not to take that meeting because it was so flattering, here is this start up, this is all so exciting, they want me to come in, and they really, really want me. I met with them and got pretty far down the process, and then I thought I have to stop because it is not the path I want to go down.
Finally, I remember having this awkward phone conversation with this guy who had contacted me, my agent contacted us, and he was one of the founders of this company. I said look, I have to step out of this process and remove myself from the process because I think this is not the right path for me. I think it is a wonderful company, it is a fantastic opportunity; but personally, I think I want to go in a different direction. I am still kind of figuring out what that is, but I think it is more around working with people, working around being effective and their work, and finding the right career fit for them, and learning what really makes them good in that career that fits them and really working more with individuals. It was dead silence on the phone and then he goes, you mean you want to do that as a job?
It was just incredulous, and then he could not get off the phone fast enough after that. I sat there after this call ended, going oh, my god; I think I just blew like the best job opportunity that could have ever come my way; what am I thinking? Then wouldn’t you know it, about six years later, guess who is sitting in my office? The very guy who is now out of work. It got bought or whatever, and he was really in this angst about what to do. He did not remember me. I casually said we might have met once before, and he said really? I do not remember that. I do not think he remembered, but it was very vivid in my memory. It was a good lesson in that it felt so awful in the moment, but years later, I had the last laugh.
Adam Taggart: That is such poetic justice there, Jennifer. I think it’s a great underscore for what we are talking about here. What we are not talking about is simply getting another job if you have one job. We are really talking about finding your real true career path, where you hopefully want to spend either the rest of your professional life or the foreseeable future. To do that, you really have to get rid of a lot of distractions, a lot of temptations that are going to influence you, either because they are nice and shiny and hot, or because you are maybe giving up some income while you are going through the uncertainty of finding your job and you are feeling those pressures. You have parents, spouses, or peers, whatever, pressuring you to go through an open door that they think is good for you. That is why all this self-introspection is so important, because what you are essentially doing is, you are defining the compass points that you are going to use to navigate your career search. The better and more clearly you define them, the more confidence you will have as you go through the stormy, murkier parts of this that you are heading in the right direction even though in the moment it feels a little scary.
Jennifer Winn: You said, Adam, what tools are most helpful? Pen and paper are extraordinarily helpful, to just write down and get these thoughts on to paper. That process – and I think you highlighted that in your book, as well – forces you to think through it, and sometimes when you see it on paper, it helps bring a lot more clarity to it. Plus it is much easier than for anyone else to help you, whether it is a career counselor to help, or someone else who is a friend or colleague. To put it on paper is something to really work with, and it gets it out of this spinning in your head. People think they are clear in their head when they are thinking about it, and they are actually not at all. They do not realize that until they start to get it out on paper, and then they realize how much murkiness is really there.
Adam Taggart: Exactly, and I can tell you from having gone through the process, it is a really painful process, it is really hard. First, you are staring at this blank piece of paper and you are trying to say how do I sum up my essence onto the sheet of paper here, and it feels really overwhelming. Then once you actually start writing, it is awful, because by putting words on paper is actually a very exclusionary process. I felt the loss of all the words that I was not putting on the paper to describe who I was. As you say, that is the progress that you make, because what you are doing is you are whittling down, you are iterating down to something that is a core kernel of truth.
Really, the way that I found that you do that is by going through the initial pain of getting something on paper, and it may be completely not accurate. It feels awful; you do not like what you wrote, you go to bed, you wake up in the morning, you take a look at it and you say, oh, gosh, these areas here are totally off base. Let me correct them. Hey, these three actually are – I still feel pretty good. You put it down again, and by the end of the week, you maybe revisit it five or six times, and you eventually get to something where you are not really making changes anymore.
I think when you get to that point; you begin to feel that you have some confidence that what is there is pretty real. Then you can start taking that and reviewing it with people or beginning to make some preliminary explorations based off it. Of course, as you get more information back, you can tweak as necessary. I completely agree with you; it is all about getting some definition down on paper. For people who are staring at that blank piece of paper, it can feel very overwhelming.
Something I found really useful is there are all sorts of tests and exercises you can go through to help you get data initially that you can then use as a jumping-off point. There are personality tests out there like Meyers-Briggs; there are aptitude tests out there; I mention a number of them in my book. I know there was one you had me do when we first sat down together, and I actually cannot remember the name of that test. Do you still use it, and if so, would you just give a brief description of what it does?
Jennifer Winn: Sure. It is an insight report, and there are actually two components to it. One is a behavioral-style tool so you understand what your natural style is, and that helps you not only figuring out what is going to be potentially a good fit career-wise, but also how other people are likely to perceive you or how you are likely to perceive other people along the way. Someone who is very introverted may struggle with having to go out and meet new people or to ask folks to talk with them informationally. We know that is going to be a challenge for them, so we talk about strategies for how to overcome those challenges.
Then the other piece to that are workplace motivators or a values report. What is really important to you? You mentioned earlier the midlife crisis. That is not an unknown thing that happens to some folks. I often find that when that is most likely to happen is when someone is going down a career part that is not fulfilling their fundamental core values of what is their motivators in life. If they can find some ways, either in their current job or down a different path, those day-to-day needs are met more. Whether you like doing new things, you like to be seen as being in a role of power, you like to be learning new things, or you like to be socially in an environment where you can do social good for other people. Whatever those may be, they need to be met or else you do have that what am I doing? kind of feeling. What is the point of all this?
Adam Taggart: Great. Let us switch now to if somebody has used tools like that and a number of the other exercises we mentioned here.
Again, for those listening, we are really talking about the Step 1 section in the book that has been launched. There are all of these exercises, and more are catalogued in there, so if you get the book, you can see the specific tests and methodologies we are talking about.
Let us say somebody has actually done the work and they feel like they have a pretty good understanding of their core attributes, core strengths, and core values. How do they then go about beginning the division process by saying okay, if I am this type of person, how do I begin painting a picture of the type of life I want to have and where my career/work fits within that? What exercises are particularly helpful there?
Jennifer Winn: I think the vision of the future can be quite helpful of saying I am not going to worry about what skills I have or what I live right now or what my like looks like now, but if I project out 20 or 30 years, what would I want it to look like then? Maybe it is just ten years. If you try to say what it looks like next year, you are so enmeshed in your life right now that it is hard to think what it could be to try to envision it being very different. You need to go out far enough to say, in a perfect world, let us say, what would I like it to look like? Where do I want to live? What do I want my day-to-day routine to look like? Do I want to the people around me? Do I want to be helping younger people? Do I want to be learning new things? Do I want to be building something? Do I want to work with my hands? Try to picture what that environment is like, so you can start to picture yourself in that environment. Then, in crystallizing that with the seven stories or some of the other exercises that you articulate in the book, you start to see where there are threads that start to connect what is right now with what you want it to be in the future.
One other thing, Adam, that I did want to touch on before we got too far away from it, which is that you mention that feeling of there is this blank piece of paper and I need to put my life down in words here. One thing that can be helpful to just sit down and set a timer for 20 minutes and say I am not going to do the whole thing right now, I am just going to knock out a quick draft my first thoughts in 20 minutes and just write down whatever comes to mind for 20 minutes. Then set it aside and do another 20 minutes, and that way it can help break through that complete gridlock that tends to happen sometimes when you are trying to write on the spot and create the perfect summary of your life.
Adam Taggart: I am really glad you mention that, because you are exactly right. One of the really key strategies here is breaking all of the work down into digestible, bite-size steps. You are really trying to answer, again, some very big existential questions and ultimately make a pretty big change in your life. As we mentioned, it feels really daunting, so the less you can make it feel like this massive solution that is on your shoulders that you need to resolve right now and you realize it is just a procession of many steps and each individual step is doable, it really a) lets you take action and
– Peak Prosperity –
NOTE: Comments from the old website are still being migrated, but feel free to add new ones. Please be patient while we complete this process. Thanks!