Overcome the 3 fantasies

TLDR 

I had been reluctant to engage the services of a career consultant. The truth was, that I was skeptical.

Looking back on it now, I misunderstood what working with a career consultant would look like. Working with a career consultant helped me to dispel the three main fantasies that had been impeding my search for satisfying work. These three fantasies were: 1) fantasies about myself, 2) fantasies about what work was out there, and 3) fantasies about the specific roles I applied to. 

Myths about myself: I refer to this as a myth of the self problem, because a lot of people, when asked to produce a list of criteria for satisfying work, list out qualities they think “should” be on the list rather than reflecting on what they actually desire from satisfying work. In many cases, they don’t know how to describe satisfaction in a way that is unique to them. The biggest problem I help my clients solve: ensuring that they have specific enough criteria for describing work that is meaningful and satisfying for them. I call these this list of criteria their WANT: wishes, aversions, needs and terms (non-negotiables). Often, high-achieving, highly successful individuals are missing a key skill they need to be able to articulate these criteria - the skill of discernment. 

Myths about what’s out there: Thwarted job hunters often have the fantasy that the available jobs out there are more limited than they actually are. Often this is because we foreclose on opportunities through focusing on what seems realistic or feasible and then filter to desirability. As your career consultant, I flip the script: I invite you to expand your field of vision by starting from the premise of what is desirable and narrowing down to what is feasible or realistic. This comprehensive approach not only reveals more satisfying options you might have overlooked but also provides peace of mind. When future doubts inevitably arise, you'll have confidence in your choices because you've explored the alternatives. The result? You'll make career decisions from a place of self-knowledge rather than fear of missing out. 

Myths about my WANTs: The final step to finding meaningful and satisfying work is to connect the work of uncovering your WANT and career scan. We assess whether your WANTs are available in the specific role you are interested in pivoting to. A career consultant helps on this journey through helping you to manage confirmation bias, or fighting the fantasy that a WANT is present when it isn’t. We do this by helping you design your interview to solicit the information you need, assist you in assessing whether you have enough information to enable you to make a decision about the career. Once you complete this step you are ready to apply to the roles that pass your screens. 

Conclusions 

In truth, my work as a career consultant continues even after we answer all the questions above. I support you through the entire job search campaign (including the interview) until you start your new role in a new company (and then supporting you through your first 100 days); or, to identify a new role at the same company; or, to identify training programs in case you need to retrain; or, to develop a business plan in the event you go into business for yourself. 

If you are having difficulty thinking about whether to engage a career consultant, I hope this will be helpful. The process can be simplified by asking 3 questions: 

• Do I have a clear list of criteria which I use to screen every single career opportunity that comes along (a catalog of my wishes/aversions/needs/terms (non-negotiables)? 

• When thinking about my career, have I cast a wide net to consider a wide range of functions and industries? 

• When looking at a specific role, have I validated through interviews whether my WANT are present in the specific role? 

I hope you can see that the single most useful thing you can do in your career search is identify your specific WANT. 

Full Version

I had been talking to my therapist about my inability to find satisfying work for a very long time before I finally took his suggestion and decided to speak to a career consultant. My therapist, a kind and (extremely) patient man, explained that work’s role in our interactions was important insofar as they affected my emotional state. He was an expert in helping me navigate those emotions and getting a sense of who I was and how I wanted to show up in the world. I didn’t want to admit it to myself when he said, but he was right, finding nourishing and intrinsically satisfying work is not therapy and it needs its own approach. 

I had been reluctant to engage the services of a career consultant. The truth was, that I was skeptical. The source of my skepticism arose from the fact that career consulting did not seem particularly rigorous. Unlike psychoanalysis, with its hundred years of history, research and proven track record of success, career consulting seemed…fuzzy. What could a career consultant do that therapists, personality tests, career coaches at a top business school / management consulting firms not do? 

Quite a lot as it turns out. 

Looking back on it now, I misunderstood what working with a career consultant would look like. In my head it would be like working with a pattern-recognition machine who would automatically diagnose me with work that I would find satisfying. This removed me from the process entirely. Instead I was deeply involved and in charge of the journey through a rigorous inter-personal process of weekly exercises and gentle questioning, working with a career consultant helped me to dispel the three main fantasies that had been impeding my search for satisfying work. These three fantasies were: 1) fantasies about myself, 2) fantasies about what work was out there, and 3) fantasies about the specific roles I applied to. 

Fantasies about myself 

Prior to working with a career consultant I used a shortcut to find meaningful work that I have come to call “people like me” fantasy. The fantasy works like this: when faced with a big decision (maybe about graduate school, maybe about a job) I believe that I can craft a path forward by comparing myself people similar to me and doing what they did. Looking for my first job out of college, I looked at my friends with the same majors as me in the year above me to see where they had taken their first jobs. Making my first lateral move, I looked at the personality test results we took at work to see where people with my traits were most likely to be successful. The alluring thing about this fantasy is that it should work: it’s data-driven, looks at a broader sample set than a single person, and appears to have a track record that appears objective and measurable (money made, graduate school, promotion speed). 

The problem with the “people like me” fantasy is that it isn’t really about me at all. It is about how I perceive similarity to people and make my decisions based on their decisions. There isn’t actually a way to identify people like you, not in a meaningful way, by looking only at the career choices they have made or by the personality traits they have displayed. It’s the reason that without self-knowledge about what drove career satisfaction for me, I kept picking work that didn’t quite fit the bill. The only way to counter the fantasy is with a systematic review of your reality: the basic starting point of a rigorous career consulting engagement. 

The simple act of explaining why I chose one thing over another in my career to a neutral, and interested observer, invited me to confront my hidden assumptions and the stories I had been constructing about myself. These stories impact every facet of our lives - our leisure time, our family and social situations, our career histories, what we think of as our skills. What matters here is not what you think, but what you actually did and why. A trained listener can help identify when you have tied yourself into knots to convince yourself of a truth that is not evident in the actions that you took. A great listener helps create an environment where you can make those connections for yourself. 

Through our work I uncovered this major insight: I had been a victim of my own success. Because I happened to be generally good at most things I set my mind to, and I enjoyed the adulation that came with success, I mistook the rush of achievement for satisfaction. And because all jobs reach a point where you stop learning new things and the wins become harder to come by, each job would run out of the juice that kept me there. 

I had never developed the meta-skill of discernment to articulate what I actually liked and disliked because I had never stopped to closely examine my experiences and choice and inquire about the specific attributes of the situation. At a basic level each session with my career consultant developed the skill because I was always analyzing my career from that perspective. The more I practiced this skill, the more available it was to me and the more granular I was able to be about articulating why a role would or wouldn’t work to provide me with satisfaction. These wants, aversions, needs and terms (non-negotiables) (WANT) were the actual criteria I needed to identify satisfying work; and they were specific to me! 

If you take nothing else from this essay I hope you remember this: learning about yourself, not just who you are at work, but also who you are outside of it enables you to develop the skill of discerning what you like and dislike. Developing your criteria for satisfying work (WANT) and the self-knowledge alone will pay off no matter what work you do. 

Fantasies about what’s out there 

When it came to pivoting jobs in the middle of my career, I had developed a short list of what I considered “acceptable” jobs. I then picked within that narrow list based on my desires. I liked this approach because my list was short and realistic. The act of truncation is a birthplace of the second big fantasy: fantasies about what’s out there. This fantasy has the effect of making you think the options out there are more limited than they actually are. I hope it’s clear that even if you are picking careers with realism in mind, starting from a truncated list means you are likely a priori eliminating the chances of your picking a job that is realistic that you might also find deeply satisfying. 

Working with me invites you to flip the script. Instead of starting from a realistic list and whittling down with desire, if you start from the premise that there is satisfying work out there and then whittle it down based on realism, you actually manage to cast a wider net that automatically includes work that you might find innately satisfying. 

These desires are so important that I encourage my clients to consider fantasy jobs. Not because they are achievable (definitionally, they are not); but because they reveal core motivations that allow us to test whether jobs that actually exist might fit what my clients are looking for. Personally, one of my favorite fantasy jobs was “dinner party host”. On the surface of it, this makes no sense with what I do today. But what I love about throwing dinner parties is that I get to create an intimate setting for important conversations, conversations where people feel connected and learn new things in comfortable spaces. This is precisely what attracts me to this profession. If I do my job right, my clients are in conversation past versions of themselves and me, and together we create the safe vessel for their insights and exploration. 

If for no other reason than peace-of-mind, starting with a long list inoculates against one of the biggest thieves of satisfaction in careers - “what if?” A career is made of many jobs. At every job, there are natural moments where you start to ask yourself what else might be out there. You start wondering if you shouldn’t have done something else. Then you are only able to see the stuff that annoys you about your job. And in this place, you get desperate and hunt immediately for a job that gets you out of the mess. When I would get to this place, I would return to my realistic list of unappealing work and reach the depressing conclusion that there was no work for someone like me. 

I’ve noticed that I get this feeling less and less the more I make decisions based on WANT and career scan. But these moments of doubt are inevitable. Now, when I get this way, I look at the long list of work I considered, I look at my short list of jobs that I could do instead, knowing that they are ones I have screened for satisfaction, and my “what if” urge fades. I know there is other work out there I could do, and I know that I could be making much more money doing it, and I am also aware of the trade-offs I am willing to make to get it. Knowing this about myself is intrinsically satisfying. “What if” never goes away completely, but its power to make me act impulsively has been strongly diminished. 

Fantasies about the specific role 

So now we have our list of target jobs, our natural impulse to learn more about them leads to the job descriptions that companies put on their websites. We read the blurbs and come to understand what it would take to do the job. If I read enough job descriptions of what it takes to be a product manager, then I will know whether or not to apply. It should be that simple, right? 

You already know what I am going to tell you. 

You will absolutely know what the job of product manager entails, but you won’t know the extent to which your WANT are satisfied. The WANT are the conditions for career satisfaction and joy, so this is a non-trivial problem. The problem gets magnified the more senior you are or if you decide to go into business for yourself - new roles don’t have job descriptions that you can compare. These are situations where you can’t afford to have fantasies about the job. You need to know which of your WANT are present and what trade-offs might be for the ones that aren’t. 

The key here is talking to people; more than three people to assess the presence/absence of your WANT in the target role. There is no good way to do this at a company where you are interested in a role, so you need to do this with a variety of people who do the work at a cross-section of organizations before you apply for a specific job. Why? The single biggest obstacle in the fantasy about the role is the fight against confirmation bias. Confirmation bias being the tendency of mind to privilege information that confirms our beliefs. Prior to working with a career consultant myself, I would usually be desperate by the time I was looking at other jobs. With my frustration and urgency for change, I was predisposed to only listening for information about the job I was interested in that confirmed I was right to leave my prior opportunity. In short, the fantasy about the specific role was that it had my WANT when that could just as easily have been confirmation bias at work! 

A good career consultant will make sure your confirmation bias is held in check through: making sure you ask about all your WANT, ensuring that you talk to a variety of individuals, and helping you identify when you lack the information you need to make your decision. This was both frustrating and reassuring. I could feel myself getting more confident with each interview and building the muscle memory of how to politely and firmly ask for details as specific as how much could I expect to make in my first year doing a job. It was also more work than I had ever done to find a job, but I will say that my confidence in my ability to find satisfaction in a prospective job has never been stronger. 

Conclusions 

In truth, my work as a career consultant continues even after we answer all the questions above. I support you through the entire interview process until you start your new role in a new company (and then supporting you through your first 100 days); or, identify a new role at the same company; or, identify training programs in case you need to retrain; or, developing a business plan in the event you go into business for yourself. 

If you are having difficulty thinking about whether to engage a career consultant, I hope this will be helpful. The process can be simplified by asking 3 questions: 

• Do I have a clear list of criteria which I use to screen every single career opportunity that comes along (a catalog of my wishes/aversions/needs/terms (non-negotiables)? 

• When thinking about my career, have I cast a wide net to consider a wide range of functions and industries? 

• When looking at a specific role, have I validated through interviews whether my WANT are present in the specific role? 

I hope you can see that the single most useful thing you can do in your career search is identify your specific WANT. The reason I say this, is because you are always aware of what the next action needs to be (if any). If you don’t know your WANT, there are only 2 possible outcomes: being overwhelmed or being discouraged. Neither or these puts you in a good position to think about where you want to take your career and, in fact, puts you in the place where you only get more of the same.