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):

This is a companion discussion topic for the original entry at

Hi Adam and Jennifer-
   I enjoyed your conversation about searching for a more meaningful career or life-path, and the various techniques you've used to help guide the process.  It is easy to feel "stuck" on the path you are on, and it is refreshing and hopeful to "re-contemplate" a path with more heart (even if sometime in the future).  

   I also like that you tell people to give themselves "permission" to be confused or not know "the answer" right away; that that's a natural part of the process.  

    I hope you do make a follow on podcast!


Thank you Adam Tagart & Jennifer Winn for a jargon-free, basic-to-the-core podcast. Agreed - many of the employed today are in their jobs for the sake of fitting a profile set mostly by the society & perhaps by their alter-ego more than knowing what they are actually good at or what gives them real fulfilment. Recession may be an opportunity for the likes of mentioned (me included) to pen down the process as suggested by Jennifer and find a renewed sustainable way to be happy & prosperous at the same time (considering the three E's on top and you below). Boy, I am glad I am still a bachelor cool

Finally had a chance to listen to this very timely podcast.  Thank you Adam! The fact is that almost everyone in the workforce in going to find themselves in "career transition" in the coming years whether they plan for it or not.  If the scenarios predicted by this site and others prove true, which I think we all know in our gut that they will, then most of us will find ourselves "employed" on much more relevant matters directly related to family, friends, and community.   In that sense, this podcast needs a Part II that connects the suggested steps of career transition to the understood concepts of the Crash Course.   Really, what kind of jobs do we need to prepare for in this transitioning world, while keeping our passions and values intact?  It's a fascinating question for me because I work for one of the largest energy companies in the country, even with large scale energy efficiency and solar energy initiatives.  and yet I know that most of my day to day efforts now will have little relevance to people's energy needs in a post crash world.  It's such a significant disconnect, even when to Jennifer's point, it must appear from the outside to be a dream job.  Adam, you had noted that we could post questions for your next visit with Jennifer, but my hope is that since you both fundamentally understand crash course concepts, that the whole session might focus on the types of needs that society and the economy will demonstrate in the coming years  and to which we in the future labor force might be preparing now (keeping all of Part I principles in mind of course!). I can imagine that this is one of the most relevant issues in 2013 where we still have time and resources to prepare for career transitions, yet lack of clarity on the needs of a future post crash economy.  (And let me be clear that I don't subscribe to a long term scenario of survival of the fittest.  History is proof that humanity seeks to build economic networks as quickly as possible.  And we have too many physical asserts in our world, not to leverage those quickly for more sustained economic well being post crash.  How do we prepare now?  Gen X, Y and Z wants to know).

I'm pleased to see you found such value in the discussion. Our careers are often such a big part of our identities (consiously or not) that even thinking about making a transition can be really overwhelming. 
Hopefully we removed some of the weight here and maybe injected a little optimism/enthusiasm for the opportunity to move closer to work that truly fulfills you.

Jennifer was a huge help to me in the process of deconstructing what makes me tick and coming up with an effective, digestible process for identifying work in alignment with it. I'm so glad to have been able to introduce the PP audience to her warm yet practical delivery of her expertise.

Bobby: I agree that recessionary periods of job loss provide the opportunity to reinvent oneself. Though, IMO, it's better to start the work now so you're not beginning from scratch after the shock of receiving a pink slip! 

spud: Yes, a companion guide that identifies careers likely to have premium value in a Crash Course-defined future is definitely in the cards. It proved too difficult for me to tackle at the same time as this first book. It is on Chris' and my radar (no ETA yet, but I'll let you know when we have one)

pinecarr: Jennifer has agreed to return as a guest. She'll likely reappear in July or August.