The Often Illogical Process of Career Transition

Are you wondering if it’s time to switch careers? Perhaps you realize that you haven’t looked forward to most of the work you do in years. Or some significant life event has occurred that causes you to shift your perspective and priorities (e.g. The birth of a child or a serious illness).  Or you’re “burned out” (as I became after almost 20 years in the fast-paced, high stress world of advertising). Or you’re yearning to do work that impacts your community or even the world in some positive way.

BUT you don’t know how to discover where that that new career path lies.

This is the dilemma with which many of my clients are struggling. Often they have taken career tests (e.g. MAPP), personality assessments (e.g. Myers-Briggs) or personal inventories (e.g. StrengthsFinder) but have discovered that the tests shed little new light on which paths to pursue. Frequently these exercises tend to reveal what they already know about themselves, or suggest directions that are unappealing.

The main reason that the kind of tests cited above often fail to answer the “what’s the right new career” question is that they rely on linear processes: straight line connections between thoughts. If you test strongly as a communicator, then you should go into a career involving writing or presenting. If you score high in empathy, be a therapist.  Analytical? Consider forensic accounting. Unfortunately, most of these career ideas have usually been considered and rejected for a variety of reasons. What's needed is a leap of thought, an inspiration, not an extension.

“We tend to think of problem solving as the implementation of logical steps toward an answer that is predetermined and inevitable.”* (At least to a great degree). “Analytical thinking and logical thinking, is all about the exclusion and critiquing of ideas so that the brain can become a guided laser that operates with surgical precision. Analytical thinking is ideal for weighing options in a well-defined problem, but that power is also its weakness: it is antithetical to inspiration.”*

Inspiration often comes from connecting seemingly unrelated dots. To quote Albert Einstein: “A new idea comes suddenly and in a rather intuitive way. That means it is not reached by conscious logical conclusions. But, thinking it through afterwards, you can always discover the reasons which have led you unconsciously to your guess and you will find a logical way to justify it. Intuition is nothing but the outcome of earlier intellectual experience."

So what do I recommend as tools to consider in helping to chart a promising new path? A combination of:

1. (Day) dreaming - When we dream the mind is freed from the constraints of logic and current reality. All kinds of crazy combinations of characters and situations appear. Allow yourself to daydream, to free associate. Make time in your schedule to do nothing rather than check Facebook for the 6th time that day.

2. Conversations - Talk with people you admire and hear about their paths to career satisfaction. Even if they’re in a field that holds absolutely no interest for you, valuable tidbits can emerge (e.g. About analogous starting points, processes, and sources of inspiration, be they people or podcasts).

3. Structured Exercises  - Open-ended exercises such as those that appear in my current favorite career book, “Roadmap” (by Roadmap Nation) can generate lots of new avenues of thinking, far more than the closed-ended multiple choice format of most career tests.

4. Professional Guidance - I’ve worked with hundreds of people to discover new goals based on existing likes, strengths, skills, and values. A particularly valuable function that I serve is to consistently support the process of exploration by providing MOTIVATION and ACCOUNTABILITY, both of which are often required to see the process through. Another is that, based on my breadth of experience, I make suggestions derived from other client experiences that may be applicable.

*From the book “Solitude” by Michael Harris


Making Friends


More often than you might imagine clients complain to me about how difficult it is for them to make friends in Washington. I used to hear the same complaints about Los Angeles, but L.A. possessed an attribute that allowed people some degree of acceptance of the difficulty - namely the long distances that separated many residents. Not so true of more compact DC. But I actually think that the difficulty of making friends for most people here is primarily due to a lack of an effective friend-making strategy.

The overall strategic thrust has several key components:

Identify and then spend time in venues that allow for person-to-person interactions that are deeper than typical cocktail party banter. There are a myriad of settings that will allow for more-than-superficial interaction. One such setting is a Meetup. Meetups are informal gatherings of people with shared interests, ranging from movies to foreign languages to entrepreneurship to technology to music to hiking to cooking.....the list is practically endless. Go to and input an activity you enjoy and see when and where the next Meetup is. Then go! It's surprisingly easy to interact with strangers when you're gathered around a shared inetrest. 

Volunteering also can provide opportunities for meaningful interpersonal interaction. Again, it's not too difficult to strike up conversations with people who share your commitment to a cause or an organization by volunteering.

Of course your workplace is another venue where you can have extended interaction with others. But in order to leverage that opportunity you need to be:

Take the initiative and be (pleasantly) persistent. This advice from is spot on: "It's a big mistake to passively wait for other people to do the work of befriending you. It's great if it happens, but don't count on it. If you want to get a group of friends, assume you'll have to put in all the effort. If you want to do something on the weekend, don't sit around and hope someone texts you. Get in touch with various people and put something together yourself, or find out what they're doing and see if you can come along.

It's one thing to hang out with someone once, or only occasionally. You could consider them a friend of sorts at that point. For that particular person maybe that's all you need in a relationship with them, someone you're casually friendly with and who you see every now and then. However, for someone to become a closer, more regular friend you need hang out fairly often, keep in touch, enjoy good times together, and get to know each other on a deeper level. You won't have the compatibility to do this with everyone, but over time you should be able to build a tighter relationship with some of the people you meet."

Don't set your expectations too high. "Sometimes you'll join a club or be introduced to your friend's friends and hope to meet a bunch of great new people. Then you get there and the experience is disappointing. You may feel like you don't click with anyone, or like they're ignoring you in favor of making in-jokes with each other. Give these groups a few more tries. Often you're limited in how much you'll connect with others on the first meeting. You may warm up to each other before long.

If someone refuses your invitation because they're busy or not sure if they can make it out then don't give up. Try again another time. Try to assume the best. Don't automatically jump to the conclusion that they hate you and you're fundamentally unlikable. Also, even the act of making an invitation sends the message that you like someone and want to hang out with them. They may be unable to meet that one time, but now see you as someone they could possibly have fun with in the future.

When you meet potential friends be realistic about your importance in their lives and how long it may take to become buddies with them. They probably already have a social circle and their world won't end if it doesn't work out with you. As such, don't get too discouraged if they're not knocking down the door to hang out with you a day after you met them. They may be busy and your plans may not pan out for another few weeks.

Network into friendships. I always emphasize networking with clients who are looking to change careers or jobs. WHO YOU KNOW is vitally important in the career realm, but it can also serve you well in creating friendships. Ask people you know who THEY know who might be good candidates for friendship. You may be reluctant to admit to wanting to make new friends, but with very few exceptions people can identify with that desire, and are likely to admire your frankness in admitting it, and be flattered that you are asking them.






Don't Let Your Mind Control You! 


"Huh?" you might think. "I'm in control of my mind. I decide what to think, and when." But for most people that's frequently not true. The mind is constantly generating thoughts, and too often one of those thoughts can capture your attention and keep you imprisoned in its narrow, frequently negative, perspective.  Consider: worry, anger, guilt, jealousy, resentment, embarrassment...these are terms that we characterize as emotions but that are primarily generated, and invariably sustained, by thought. The proof: the large majority of the time people gripped by these emotions are reacting RETRO or PROactively, disconnected from the triggering action in time and, usually, in space. When you're in their grip you've lost control - it's all you can think about. Some examples: 

CAREER: Will I get promoted? Why doesn't the recruiter call me back? Suppose I get downsized? I can't believe I wasn't invited to that meeting. This place is too political for me. I hate having a windowless office. How come the boss pays more attention to her? 

RELATIONSHIPS: Why didn't she answer my text? I always pay for dinner. If he only lost a few pounds I'd be more interested in sex. She's too wish-washy. I wish he would do something other than watch sports.  I can't believe my mother talks to me that way. 

If most of those thoughts related to productive analysis or processing it wouldn't be so wasteful, but wasteful it too often is since the thoughts tend to remain in a loop that simply replays the disturbing event and your initial reactions to it over and over again. 

It's unrealistic to expect that you can completely free yourself from this lifelong pattern. But it's quite possible to significantly reduce the amount of time your mind churns. How? By practicing observing when and how these loops emerge. As you observe the workings of your mind you are separating yourself from it, which is the key. You are NOT your thoughts. 

There's a simple observation exercise I particularly like. First, close your eyes and begin slow, deep breathing through your nostrils. Notice the subtle, slightly ticklish feeling in your nose as the air goes in and out (if you can't find that sensation, try pursing your lips and pay attention to the feeling of the air brushing against your lips as you breathe). This should be where your mind focuses during the exercise. As you begin the slow, deep breathing your mind will, within a second or two, generate a thought, seemingly out of nowhere. * Just notice the thought but don't evaluate or judge it (or better still, simply notice that you had a thought). Then bring your attention back to the ticklish sensation in your nose. Keep doing this for 5 minutes to start, going up to 10 in a week or so. If you're like most people you'll find that one of those random thoughts engages you and, before you realize it, you'll have spent a minute or several minutes "captured" by the thought before you remember to refocus on your nostrils. 

The exercise not only enables you to observe the constant churning of the mind but also allows you to strengthen your "mental focusing muscle" so that you become better and better at putting your mind where YOU want it to be as opposed to where your mind drags you. It's a really great way to strengthen your control over your mind, your most priceless asset.

*Sometimes a thought will be generated by an outside noise, or perhaps an itch, but generally no stimulus is required!


Follow Your Bliss? Not So Fast!


The most prominent "common wisdom" about finding happiness and success in your career is that first you must identify your passion and then pursue it with determination. This template for career fulfillment was popularized by Stephen Covey almost 30 years ago in his famous book "The Seven Habits of Highly Successful People," and it's been pretty much the dominant narrative thereafter.

Since I discovered the book "Roadmap Nation" late last year I've prescribed it to many clients as a prompt to uncovering obstacles to career progress and as a stimulus for ideas for career exploration. Generally the book is well received, but several of my clients have protested that some of the case histories in the book don't really resonate with them. Why? Because they deal with people who in fact had a passion early in life but then ignored it as adults until their dissatisfaction with their careers led them to a path that wound up directing them back to their passion, ultimately leading them to success and happiness. "But I never had a passion like that" these clients complain.*

Cal Newport, the author of "So Good They Can't Ignore You," takes a different tack. "The conventional wisdom on career success - follow your passion - is seriously flawed. It not only fails to describe how most people actually wind up with compelling careers, but for many people it can actually make things worse, leading to chronic job shifting and unrelenting angst's reality inevitably falls short of the dream," (Or in other words when it turns out that the job on the career path you felt passionate about turns out to be mundane).

Think about it - doesn't it make sense that it's awfully hard to know in advance how passionate you're going to feel about something if you've not immersed yourself in it before?

Newport writes (with quite a bit of supporting data) that most often people discover their passion only AFTER investing a significant amount of time and effort in an area**, an investment that leads them first to increasing expertise (Daniel Pink in his book "Drive" calls that Mastery), which brings with it a powerful sense of satisfaction. The satisfaction arises not just from knowing that you're good at what you do, but from seeing how the good work that you do benefits others or and/or makes an impact. Then, as this mastery is achieved, opportunities for advancement multiply. Newport characterizes this accumulating mastery/expertise as "career capital," which can be exchanged for positions of greater and greater control (Daniel Pink calls that "autonomy"), which he views as the single most important element of career satisfaction.

While all of this makes a lot of sense, the issue I have with it is that it's hard to know where the right place/time is to invest the effort required to develop the mastery necessary. Should you invest in your very first job (or, if you've changed careers, in your very first job on the new path?). I believe the answer is "yes." You've taken your best shot at landing the right job, so give it your best! Develop your skills and expertise. If, after a while, you feel you've made the wrong choice, do some research and craft some "betas" - little experiments in other fields that could reveal a path that's more likely to result in fulfillment. So let's say, for example, you're an associate at a law firm but are discouraged about your long-term prospects for happiness. You might want to talk with some people who have successfully transitioned to other paths, and then engage in some kind of extracurricular work related to those other paths (joining groups related to, volunteering to work in, attending conferences about those other paths). 

Newport suggests that there are three factors which, if any are present in your current job, should make you look to depart. One - the job presents few opportunities to distinguish yourself; two - the job focuses on something that you feel is useless or perhaps even bad for the world; three - the job forces you to work with people you really dislike. If any of these are present, look for other work. I highly recommend that you do the exercises in "Roadmap Nation" (or, if you're creatively oriented, in "Designing Your Life" by Bill Burnett and Dave Evans) as an excellent way of identifying a new, promising path. And when you find it, invest in doing the hard, challenging work that will make you valuable in that field and will lead to the advancement and increased control that will contribute so strongly to your career fulfillment.

*Fortunately, the book also contains numerous examples of people who only discovered their passion after extensive experimentation, a bit of luck*, and hard work. Luck often takes the form of conversations with new or old acquaintances or even strangers, who reveal a door to walk through, a door that was undiscovered or invisible prior to that conversation. This emphasizes the importance of connecting with others in the process of exploring career possibilities.

**Newport emphasizes that the effort required to gain the necessary expertise should come not just from an investment of significant time, but from time spent tackling challenges that push you outside of your comfort zone, so that you gain new skills rather than simply improving on old ones.


Emotional Factors to Consider When Exploring Career Options

The majority of the work that I do with clients involves helping them to first identify and then explore promising alternate career paths. To give structure to this process I frequently use one of several career exploration books that contain what I have found to be useful exercises. These exercises identify factors that I then explore with my clients through questions and dialogue, clarifying, and narrowing possibilities.

There are 5 books that I particularly favor: Roadmap (by Roadmap Nation), Designing Your Life (by Bill Burnett and Dave Evans), Getting Unstuck (by Timothy Butler), The Startup of You (by Reid Hoffman and Ben Casnocha), and I Could Do Anything If I Only Knew What It Was (by Barbara Sher). Based on my assessment of my specific client's background, career history, and personality I will recommend one of these to utilize. They each come at the question of "What's the best new career direction for me?" In different ways, but what they all have in common are probes to illuminate the likes (and dislikes), strengths (and weaknesses), and values that will help pinpoint the right next career direction. Some use the concept of "flow" (first identified by Michael Csikszentmihalyi), asking readers to think about situations or activities in which they were so engaged that they had little sense of time passing.

There is one area that they don't explore/explain as well as I’d like them to, though, and that is the core EMOTION that is triggered by certain work. Likes and strengths, for example, are generally focused on things like specific fields (e.g. business, education, travel, politics, or science) functions/activities (e.g. analyzing, writing, designing or organizing) or outcomes (e.g. contributing to the creation of a finished product, advancing a cause, having a positive impact on others, making a lot of money). 

As a result of many years of self-examination and working with many hundreds of clients, I have come to realize that what may really be central to figuring out the optimal career direction for some folks is identifying the feeling that underlies their enjoyment of various fields, functions, and  outcomes. Barbara Sher calls it your Touchstone. Roadmap Nation terms it your Foundation. In my own case, I have quite recently come to realize that what brings me the most enjoyment is just about anything that makes me feel smart. Over my lifetime that has manifested itself in numerous forms: raising and waving my hand frantically because I had the answer back in elementary school (yes, I know, obnoxious!), often speaking first during a case study class at Harvard Business School, taking particular pride in my win on Jeopardy, and currently absolutely loving the work I do instructing others on ways to improve their careers and more broadly their lives.

I'm not sure how many people have this kind of significant underlying emotional touchstone but my guess is that it's a fairly substantial number. This is something I will be exploring going forward, but I would ask you to contemplate whether such an emotional touchstone could exist for you. Think about those situations, those moments, when you felt particularly great about what you were doing - not just in your work life, but in life in general. Then try to discern what emotion was triggered. Perhaps you felt brave, noticed, or superior. Helpful, popular, or inventive. Put your candidate emotion to the test - see how broadly it applies to various circumstances of your life. You may uncover an important key to helping you discover the ideal ultimate calling for yourself, and an aid in chart a nearer-term career path forward.