How to Think Through a Career Change

“I’m in the wrong career and I want to know what the right one would be.” Jason had a winning smile, bright penetrating eyes, and a capable, confident, easy-going manner. As a graduate of Harvard Law School, I could also assume that he was intelligent and hard working. His large law firm had probably been delighted to recruit him not only because of his attractive personality, but because minority hires with his outstanding academic credentials were highly desirable and not always that easy to find. “I’ve been a commercial litigator for three years,” he went on, “and I hate almost everything about my job. In fact, I never liked studying law in school. I am not interested in the subject matter and I don’t feel I fit in with the people I work with.”

Jason had chosen law as his career for many of the same reasons that others do. In high school he had been told that he communicated well and held up his end in an argument. Jason was an excellent student from a tough inner-city high school where he was the school president his senior year. He excelled at basketball and loved to play the game. Jason went to Amherst college and, after an initial adjustment, he did well there. Jason’s teachers as well as his parents encouraged him to consider the field of law because it would be a secure and lucrative profession.

The first inkling of trouble came in law school. Jason did well in law school because he worked hard, but he had no interest in the legal concepts he was learning. He persevered because many people told him that the practice of law was not like law school. Maybe he would enjoy practicing law.

In his first and second summers during law school he interned at the law firm that eventually hired him when he graduated. This large firm had a reasonably good reputation for quality of life. Jason worked in the litigation practice group. He described the practice group leader as a “decent guy” and the others in the group were “kind of boring but okay,” according to Jason. As time went on, however, it became clearer and clearer to Jason that for him the work wasn’t what he wanted to spend his time doing, and the legal issues were uninteresting to him.

Jason was, he said, a “real people person” who liked to be “physically active”. He looked at the partners at his firm and realized that he did not want their jobs or their lifestyles. Ever. Big money did not motivate him. Jason felt that he was wasting his time as a lawyer at a large firm. Other people might think that his life was “cool” or “prestigious” but nothing could convince him of that. He hated going to work and couldn’t wait to leave at the end of the day. Every Sunday he got depressed.

What did he want from his work-life? Jason described his ideal job. He would look forward to going to work. The workplace would be “active” and involve a team with a mission that excited him. He would interact with a lot of people during the day. He would feel good about the mission and the goals. He would be involved in a work world that brought out the best in him. When we went through his work history, the job that he loved above all others was the job he had had coaching the women’s basketball team in college. He enjoyed the activity, the counseling and coaching. He loved the thrill of the games and the administrative work did not bother him because it was part of the effort needed to make the team successful. He liked everything about that job. On a scale of 1 to 10 that job had been a 10.

What set Jason apart from some dissatisfied professionals I work with was the knowledge he already had about his career dissatisfaction. Jason was certain that his job and probably his career was wrong for him. He knew that he needed a roadmap to help him find a career that was better for him. He had already given a lot of thought to what would make him happier.

Some of my clients begin our first session with a tangle of undefined depression and weariness.

After trying for years to unravel the cause of their unhappiness by themselves or with the help of books or spouses or friends who are tired of hearing their complaints, they meet with me to help them solve the mystery of their dissatisfaction. All they can say is that they are unhappy, but they do not know why.

No matter how confusing or mixed up the initial ball of complaints may seem, it is usually possible to untangle it by identifying four elements and using these elements as a device for sorting out the dissatisfactions and needs that must be met. This, along with a work history helps us understand the basic building blocks for a successful career.

These four elements we discuss are: aptitude, interest, lifestyle, and self- actualization. They form the acronym AILS. Each person needs to have a differing amount of these four elements in his or her career, but everyone needs to get these four elements to experience career satisfaction. If you are unhappy ask yourself “What AILS me?” by thinking through how well or how poorly your current career is satisfying these elements for you.


Aptitude is what you do well. You want to have a career where you get to play to your natural strengths and your natural talents. Others may describe you as “terrific” or “excellent” at these activities.

Usually aptitudes are not speculative by the time you graduate from college. By then most people have experienced, recognized and have evidence of their talents and gifts. Other people such as your parents, teachers, and friends have pointed them out to you. “Wow, you sure are good at public speaking,” or “I can’t believe how well you understand people and you are so good at helping them feel better,” or “You just always seem to understand math. How do you do it?” Often you will be able to tell that comparatively and objectively you do well at these activities. You are the person who is asked to take a leadership role. You are the person that everyone seems to trust to tell their secrets. You are a stand-out in your science class. In short, you do the task or activity well and you are naturally good at it.

There are also aptitude tests that can be helpful for people who want to be sure about their strengths or gifts and avoid missing a hidden aptitude that might influence career path choice. Aptitude tests are especially helpful for people deciding on their initial career path. Once you have invested significant time and energy in a professional career and have developed a skillset that is marketable in that industry, it may be less useful for you to be told that you should have been an architect or a doctor, for example. At that point in your life, the energy and/or cost it would take to recredential in a field that demands years of study and internship or other hurdles, may be impractical, too expensive or too time-consuming for you.

On the other hand, there are often related fields that will allow many professionals to enter with little or no re-credentialing. For example, many attorneys are able find niches in the legal profession that play to their strengths, eliminating the need to re-credential. Or they might find a career that relates to the field of law or serves the field of law where the legal background acts as leverage and gives them an advantage- these are called JD Advantage jobs. Some examples are professional development for law firms, sales of technology services for law firms, career services in a law school, public relations for the legal field or legal recruiting. There are many others. If you transition your career into the new field you will no longer practice law, but your legal experience makes you more valuable because you understand the legal work world and you serve or support some aspect of the legal field. From that strategic move, you can sometimes move further into the new field. You can go from legal recruiting to executive recruiting, or career services for the law school to another role in the administration of a university. Other professions have the same kind of potential for people who want to leave the direct delivery of services in that field but can deliver valuable services to the industry in a different role. An example would be changing careers from being an environmental consultant doing field work to the role of strategic communications director for a renewable energy company. There are many other similar transitions that can work for people who are trying to retool their careers to play to their strengths and interests.

In Jason’s situation he seemed to have an aptitude for the law that would have sustained him had he been interested in the law, but he was not interested.


Interests do not always match up with aptitudes. You can have an aptitude for math but be uninterested in a career where you use any of your math skills. Your “interests” are important because they provide the energy or motivation powering your work-life. You like to think about the kinds of things or ideas or engage in the kinds of activities that are typical for this field. When you choose a well-matched career the feeling is “What!? They pay me to do this work? I’d do it for free! It’s fascinating.” You enjoy the mental life you experience when you do this work. You are excited about the work and look forward to getting better at the same or similar activities.

Some people tell me they have no strong interests. Those people tend to have a strong interest they have not identified. They usually care about having a life that works with friends and family and good experiences. This can be a strong interest too!

When you are really interested in something, the whole world falls away. It’s as if you are in another world because you are so focused, so “into” whatever it is you are doing. This is referred to as “flow”. In career work I strive to find out where there is a high level of interest to help my clients who want or need to re-purpose or re-tool their careers in a better direction. Of course, we also need to factor in other elements as well including the amount of money someone needs to make, work-life balance, market forces, and whether the person must return to school for more education if that is needed to gain the skills to land a job in the new field. I worked with a young man who was sent by his parents because he had “no interest in anything.” All he wanted to do was play video games. He was terrific at these games. After working together, we both agreed his passion and dream was to be able to create videogame content. He was excited to go to school to learn how to create video games. This career path allowed him to follow his strong interest.

For Jason, strong interest in the law was missing. He reported a sense of monumental boredom with not only his practice area and the work he did at his firm, but he had also disliked law school. The content of his law school classes was not engaging for him. He had gritted his way through law school, and he was gritting his way through as a lawyer. When he looked at the people who were partners at his firm and imagined himself doing what they were doing he felt uninspired and depressed. That vision of a future life was not something he wanted.

When the “interest” factor is present, the person enjoys learning, reading and doing the activities that lead to greater expertise. Because Jason had only been in one job for his entire legal career, we thought it might be premature to think that the field of law was uninteresting to him. We considered other practice areas. Jason did informational interviews to see if other practice areas might appeal to him. He found lawyers in different practice areas through his law school career services center and either met in person or talked with them over the phone to find out about their experiences to see if he could imagine himself doing the work they were doing.

In Jason’s case, it seemed possible that his interest in sports and his background in law might fuse to create an interest in sports law. But after doing informational interviews with people in the niche practice area of sports law, Jason rejected that idea. He did not want to do legal work for athletes, which he learned would mainly mean contract negotiation and drafting. Jason also considered and rejected being a scout or an agent for athletes after doing some informational interviews with lawyers who had transitioned to that kind of work. Jason did not find any legal practice area that held his interest. If anything, after talking with other lawyers he was more determined than ever to leave the field of law. His lack of interest in the law was undeniable.

Life Style

Life style is a composite of factors. Some people really need to have these factors in their work-lives to be successful. Some do not. These factors differ in terms of importance depending upon the person. Some of these factors include but are not limited to:

  • How much money you want or need to earn to feel secure
  • Work/ life balance
  • Typical hours (time for family and friends or activities outside of work)
  • Flexibility and ability to work remotely
  • Travel schedule
  • Flexibility of place- being physically active during the day

These and other factors have varying degrees of importance for people. For some, there are items on this list that are crucial and other items that would need to be added. There are other people who would not put any of these items on their personal radar screen for lifestyle.

When I work with clients, we do a thorough work history. Clients write up the work history with a pro and con list of everything they liked and did not like in their past work experiences, past school experiences, past jobs and current job. We also talk about their family of origin and their experiences growing up. A work history and personal history illuminate themes that reveal lifestyle needs as well as aptitudes and strong interests. A thorough and penetrating discussion of these recurrent themes is the key to identifying elements that people need and need to avoid in their work-lives. Important elements recur, and “pop out” in the work history.

For example, Jason identified a need to be physically active. “I feel pent up at work all day,” he said. “I used to like being able to move around and go from place to place in college. My classes were in different parts of the campus. I really liked that walk.” “I look at the partners at my firm and wonder when they ever get the chance to exercise.” To feel okay, Jason needed physical activity in his daily life. When he played basketball, which was something he did well growing up and in high school, he felt that he was in his element. His favorite job had been assistant coach for the girl’s basketball team. Doing that job, he got to be physically active and he was also coaching, teaching, advising and training- all activities he enjoyed very much. The mission of helping the next generation was very motivating for him. Working with the team was absorbing and gave him a sense of flow.

For many dissatisfied professionals, voicing complaints and unhappiness has been a recurrent topic of conversation with colleagues, friends and spouses; enough to wear them out sometimes. Unfortunately, complaining does not usually get you closer to a solution. But the exercise of articulating likes and dislikes in a work history ferrets out these major themes and needs that people have and that can in turn lead to a better understanding of the right career direction for success.

Jason and I learned about his needs and allergies through his work history. We came up with a master list unique to Jason as I do with hundreds of other clients who work with me to identify their career direction. I highly recommend doing a work-history where you identify pros and cons of your past jobs, paid or unpaid, if you are trying to figure out the right career direction for success.


The fourth element is self-actualization, self-growth and/or personal development. It is the hallmark of being human that we are each unique and that we usually feel good if we are working towards personally resonant goals in our lives.

Just as plants need the right kind of soil, amount of sun, and nutrients, people have internal psychological needs that relate to their potential for growth. If you put a person in the wrong work context that person will not grow as well and will not feel satisfied or be successful in that career. There are also toxic workplaces with bosses that denigrate workers, screamers, yellers and micromanagers. Some workplaces are not good for anyone! In some cases, the person in a toxic workplace will feel depressed and use alcohol, drugs, or other self-medication to try to deal with the problem. Some people will blame themselves for their unhappiness at work. In my work with many clients, if the workplace is the problem, moving to a better workplace with a better environment is the cure. In addition, if the personal mission matches up well enough with the career, many people experience a sense of relief and greater contentment as well as personal growth. Given the variety of workplaces out there in the world, it is usually possible to find a better fit to match your needs.

Our careers should help us to grow and to develop in ways that we want and need to evolve as people. To do that we want to put ourselves into career contexts that promote those parts of ourselves that we want to develop. The young woman or man who was shy in high school and college or grew up in a household with an overbearing parent, might yearn to develop his or her ability to stand up, have a voice and speak out. Conquering an ancient fear can be a powerful force for personal growth as well as a motivator creating long term interest in in a field because it satisfies a profound personal need. A person raised in a household where the oldest son was allowed to bully his younger siblings may feel actualized by a legal career in which s/he can take the role of the avenger (i.e. prosecutor, public defender, personal injury attorney). The context of the workplace should support and nurture the positive personal mission of the individual.

Careers come in many different varieties when it comes to these self-actualization needs. For example, a person who blossoms when he or she can assume leadership roles and an opportunity to assume responsibility might find good opportunities in many fields as long as the work settings permit or foster that kind of growth. But let’s say a person has a strong need to have a calm and supportive team environment, with people who ask how you are feeling, appreciate you, thank you and work collaboratively. A person with that kind of self-actualization need will be less likely to find many satisfying workplaces where the firm or company has a high intensity, competitive culture. Searching for and finding the right match between workplace culture and your personal needs is very important. I teach my clients how to do this and I have written two books that help people to find their way to the right workplaces.

Some of my clients report that the career they have chosen is not working for them because they do not like the way they have to behave or act in order to be successful. They do not like the person they are becoming in order to do the job well. “I’m turning into a witch! I yell and scream at people!” one female litigator announced. “If I don’t leave the law, I will probably ruin my marriage I’ve become such a bitch.” Other lawyers have said, “I hate to pretend that I actually enjoy winning at any cost. I really don’t like the whole competitive thing. I do not want to have to act in a way that isn’t me.” Many others have said, “I think I am becoming a worrywort. I worry all the time. Did I do it right? Will the partner throw me work at the last moment on Friday when I am leaving for my friend’s wedding? Did I blow a deadline? I used to worry about things before I became a lawyer, but not like this!” Others say, “My partner finds fault with everything I write and re-writes it all in his style which makes me feel like a failure.” These and other problems bring people in to work with figure out if they should transition to a new career or simply change their workplace to get a more compatible work environment.

Another aspect of being human is that in our families of origin, we also have experiences that set us up for allergies towards certain people and situations. Many of these allergies come from our childhood, the parenting we had, and the kinds of experiences we had growing up. Without question people also bring their personal baggage and allergies with them into their work lives. Even so, workplaces can increase a person’s problems and intensify psychological distress. The measure of the job’s fit with a person’s internal needs for self-actualization must be determined by that individual’s unique blend of requirements. That blend includes quirks and sensitivities.

One person may be allergic to the micromanager boss who is reminiscent of the over-involved mother that he or she could not wait to get away from. Ironically, he now has to deal with a boss who brings up the same feelings in him. Another person might be allergic to a situation in a work group where highly credentialed attorneys (prestigious schools) do better than attorneys with more experience (street smarts) by being given better assignments and greater responsibility. It isn’t fair. Anyone might be upset about that. But if the experience reminds you of a painful rivalry with a favored sibling, for example, that will intensify your allergy to the unfair work situation and make it unbearable for you.

Everyone has these sensitivities or allergies and carries them around as personal baggage. If your personal allergies are interfering with or even torpedoing career and personal success, and/or a sense of abiding satisfaction with life, relationships and work, then it pays to unpack the bags you carry and try to understand or even remodel yourself if you can. Some people are able to do that through individual or group therapy, CBT or DBT work, counseling, journaling, or talking with family or friends.

There is a way to figure out with reasonable accuracy if you have an embedded personal allergy that is hurting your career success. If the workplace problem is coming from your personal baggage, you will usually find this problem has cropped up in other past work settings and in interactions with friends and family. Often, the work history will reveal that the person has a history of similar reactions or feelings in multiple settings.

If you want to try to figure this out for yourself, write up your work history: every job you have had, paid or unpaid, and what you liked and did not like about it. Then read it for themes. A history laced with similar stories about “bad bosses” or “people who never get along with me” or “older supervisors who always criticize me” can be a big red flag to help you to identify your own psychological baggage or allergies. If you carry this baggage with you it will follow you in life. You might want to consider therapy or counseling to move beyond these recurring problems from childhood.

In many cases there is a mix or blend of elements that contribute to workplace dissatisfaction. The person has an allergy or sensitivity and the workplace exacerbates it. If that is the case, moving into a different workplace with fewer allergens present can be a highly effective cure for the problem. The person who is, for example, highly allergic to the micromanaging boss will do a lot better in a different work world or workplace with a boss who trusts him or her to do the work. Although the underlying personality problem is still there, the problem is less evident because it is not stirred up at work.

When it came to Jason, changing to another law firm, going in house or finding a government job was not going to be the solution to his career problem because he would still be practicing law. He did not have problems with the culture of his firm, his partners or his colleagues. Jason needed to transition his career out of the field of law. After doing some informational interviews to learn about sports administration, Jason applied for a masters in sports administration at Amherst and got into the master’s program. He learned that his law degree should help him to land a good job in that new field once he graduates. Jason was excited about this transition. We can predict that he will be successful in his new field because all four elements are very likely going to be met based on his informational interviewing- aptitude, interest, lifestyle, self- actualization.

Final Thoughts

Aptitude, interest, lifestyle and self-actualization are the building blocks for a successful career. If you understand this much about yourself and your needs, you will be able to identify career goals that play to your strengths and set you on a path to career success.

What Can Trevor Noah Tell You About How To Find a Good Career Path?

Trevor Noah Born a CrimeTrevor Noah, the host who replaced John Stewart on The Daily Show, has written an extraordinary book about his experiences growing up in South Africa. The title of the book is Trevor Noah: Born a Crime. I enthusiastically recommend it!

Trevor Noah was the offspring of a South African mother and a white man who was her friend but not her husband, at a time when in South Africa, relations between the two races was against the law. He was raised by his adventurous, rule-defying, and yet deeply religious, caring, and wise mother. She taught him not to believe in limits.

“My mother took me places black people never went. She refused to be bound by ridiculous ideas of what black people couldn’t or shouldn’t do. She’d take me to the ice rink to go skating. Johannesburg used to have this epic drive-in movie theater, Top Star Drive-In, on top of a massive mine dump outside the city. She’d take me to movies there; we’d get snacks, hang the speaker on our car window. Top Star had a 360-degree view of the city, the suburbs, Soweto. Up there I could see for miles in every direction. I felt like I was on top of the world. My Mom raised me as if there were no limitations on where I could go or what I could do.”

This wonderful image and great insight explains so much about how Trevor Noah could come from apartheid South Africa, where he was only able to make it as a local hustler in the ‘hood in his early adult life, to become the talented, creative and quick-witted host of The Daily Show.

Trevor Noah writes this:

“We tell people to follow their dreams, but you can only dream what you can imagine, and, depending on where you come from, your imagination can be quite limited.”

This is true for so many people. When I work with clients to figure out a better career direction, one of the first things we do is to imagine a different future, one that plays to their strengths. I ask them to imagine a workplace they would want to go to every day. I ask them to think about a mission or missions that excite them. We talk about what they would do if they won the lottery. We talk about how they would fix their present job. We mine their pasts for information that will unearth strong interests and motivators, as well as aptitudes or natural talents that will help them rise to the top of their chosen field. This doesn’t always get them everything they want, but usually gets them a lot closer to a work life they will enjoy.

If you have not had the experience of imagining a different and better future for yourself, it can be very hard to dream of a career that goes beyond the norm you know in the corner of the world where you live and grow up. Ask yourself what you want to do in life and then stretch that idea further. If you can dream it, you can try to work your way toward it. Identify the goal, and then plan the steps you want to take and start out on that path. Even if you do not end up getting to the exact goal you set, you are on a new and challenging path, which is in itself more gratifying.

I counsel many people who, when looking forward to an alternative career will say, “I cannot imagine being able to achieve the goal I am setting.” But I also counsel many people who, looking back on their lives say, “I am amazed about what I have accomplished in my life. Who would have thought I would someday be the head of the Chicago Bar Association?” “Who would have thought that someday I would be able to run this company and have it be a success?” “Who would have thought that I could become a well-known broadcast journalist?” “Who would have believed I would be able to write blockbuster novels?”

I want to be clear. Just because you have an idea of what you want to accomplish in your career doesn’t mean that you will actually get there. But often the goal is less important than you might think, because the process itself is also gratifying.

In my own life, when I was in college, I watched some of the Chicago Seven Trial in federal court. After that, I got it in my head that I wanted to be an Assistant US Attorney. At that time being a prosecutor was not considered to be a viable career path for a woman. It was a goal that was beyond the range of what I thought was possible. But after seeing a few days of that federal trial, I was so excited, I didn’t care that it was not supposed to be a good career for a woman. I did not know I would actually be able to achieve my goal, but I took the necessary steps to try to get there by studying hard for and taking the LSAT, going to law school, landing a job as an Assistant State’s Attorney, and working in the Official Misconduct Unit because it was similar to the work done by federal prosecutors. I also networked in a creative way to meet key people who could help me interview at the U.S. Attorney’s Office. I am happy to say I was able to achieve my goal, and it was a fulfilling job. But even if I had never become an Assistant US Attorney, I had decided on a path I believed in and felt challenged by, and that was gratifying in itself. If you believe in the road you are on, the journey is actually part of the reward.

As Trevor Noah says:

“… the highest rung of what’s possible is far beyond the world you can see.”

So dream beyond the highest rung! You might surprise yourself.

What Advice Would I Give my Younger Self?

Recently I did a talk for the Posse Scholars in Chicago about how to develop relationships that can open doors for internships and jobs. The audience consisted of about thirty very engaged and interesting young men and women who were either in college or about to go to college. They had qualified to be Posse Scholars, participating in a rigorous process designed to find high-school-age leaders with smarts, good judgment, and motivation, and chosen to participate in a support program at some of the top universities and colleges in the country.

49 woman-thinking-sm

After my presentation, I opened the conversation to take questions from the audience. One young man asked, “What advice would you give your younger self? What would you say to yourself when you were our age, now knowing what you know?” That was a very interesting question. Here is the answer.

When you start out in a career, you never really know for sure where it will lead you. You want to begin with a goal based on self-knowledge, which includes understanding what you do well and what you find deeply interesting and satisfying in terms of content. As you make your way to that career goal, your ultimate objective might well shift and change. It often happens that along the way you find a path that takes you off the road you envisioned and in an interesting and appealing new direction. That’s okay. Do not think you have to stay with the goal you set for yourself originally.

However, it is really important to have a goal. Without a goal you can feel adrift and lose your sense of purpose. I counsel many people who have been “wandering around in the career woods.” They chose a path or simply started on a path because it was easy or it was something they were told ought to be good for them. But they did not affirmatively choose it. As time went on, it proved to be unsatisfying. They come to work with me to try to figure out the right career direction. Sometimes they just need to find a career direction that plays to their strengths based on shifts in the world or changes in their own priorities. It’s all okay.

One of my favorite songs is Gerry Rafferty’s “Get It Right Next Time.” Here are some of the lyrics.

Out on the street I was talkin’ to a man
He said there’s so much of this life of mine that I don’t understand
You shouldn’t worry yes that ain’t no crime
‘Cause if you get it wrong you’ll get it right next time, next time…

You need direction, yeah you need a name
When you’re standing in the crossroads every highway looks the same
After a while you can recognize the signs
So if you get it wrong you’ll get it right next time, next time…

You gotta grow, you gotta learn by your mistakes
You gotta die a little everyday to try to stay awake
When you believe there’s no mountain you can’t climb
And if you get it wrong you’ll get it right next time, next time…

I would tell my younger self it is perfectly okay to feel confused at the crossroads. Know that it will be a worthwhile journey if you are true to yourself: follow your talents and strong interests, affirmatively choose your goals, and learn from your mistakes. Don’t worry if the goal changes over time because you never know where life will take you and if you get it wrong you’ll get it right next time.

The Mentoring Dilemma at Busy Law Firms

“I‘m supposed to talk with you about why I‘m not performing well.“

I could tell by her voice over the phone that she was not happy about this. Kelly‘s law firm asked her to contact me, an executive coach, to learn how to improve her game. She was a fifth year doing transactional work at a large New York firm.


“What do you think is the problem?“ I asked her.

“It‘s not what they think,“ she said irritably. “They think I am not performing at the level of a fifth year, that I need to be more organized and use better judgment, and stop procrastinating.“

“And what do you think is going on here?“ I asked.

“I think they are not mentoring me enough. They are not giving me the support I need to do the job well.“

We discussed her situation in more detail.

Kelly had begun her career at this firm as a litigation associate, but after a year she had requested a move to the transactional group where she felt more comfortable with the role and more interested in the work. She made that transition without losing any seniority, but she felt under pressure to perform at the level of a second year even though she was more appropriately a first year associate. Nonetheless, she worked hard and was gaining confidence at that point in her career, she told me.

However, the transactional group experienced a slowdown in business. Kelly was asked to return to the litigation group to help out doing discovery on a big case, or risk being let go. She went back to the litigation group with reluctance, hoping to return to the transactional group as soon as possible.

After the litigation matter settled, Kelly requested and obtained a return to the transactional group. When she returned to that group, however, there were fewer attorneys in the group. A year had gone by. All of the junior partners had been let go or had left of their own accord. Partners were doing the work that had been relegated to junior partners in the past. Consequently, the partners were extremely busy.

“And a lot more crabby,“ Kelly assured me.

Kelly returned to the group as a fourth year associate. She was also the most senior associate remaining in the group.

She struggled to get up to speed. Faced with a difficult question, or an instrument she did not recognize, or the need to make a crucial judgment call, she would ask one of her two partners for guidance. Very often they reacted to her requests with annoyance, telling her to use her own best judgment. But when she made a mistake after doing just that, the partners expressed their frustration with her.

Her reviews suffered because she was seen as inappropriately unsure of herself.

Understandably, after receiving this feedback, Kelly hesitated to ask for additional help from these two partners, for whom she did most of her work. She tried to get assistance from another partner in the same practice group, but he too was very busy.

Her reviews continued to be negative. Her partners now faulted her for procrastination and a slow turn-around time.

“What do they expect?“ she said. “When I get stuck I have no one to turn to for help. So I just sit here unable to figure out what to do. I feel sort of frozen. When I try to make a decision, I just don‘t have enough information to come up with a solution.“

Kelly‘s dilemma is not an isolated occurrence. With an increasing focus on managing costs, I am seeing many lawyers with similar problems. Some law firms have scrambled to keep associates, moving them into busier practice areas, while reducing the ranks of junior partners. Firms have made these strategic shifts to ramp up productivity and preserve senior partners. Kelly and others like her get into a Catch-22 situation. In her case, she could ask for help and risk being labeled as lacking judgment, or she could avoid asking for help but risk being labeled as a procrastinator. The underlying problem is that she needs more training and education to function well as an associate at her designated level.

These days more than ever before, busy partners want associates who will do their jobs without needing what partners think of as “hand holding“ and what associates think of as “mentoring“.

What are Kelly‘s options?

  1. She could try to find a partner, junior partner, more senior associate, or even a paralegal who would be willing to teach her.
  2. She could try to formulate one or two approaches based on what she does know, and request assistance from the partners who assigned the work when she is able to present more well-developed ideas or strategies. This would show the partners that she is capable of advanced legal thinking.
  3. She could try to find a mentor/teacher outside of the firm.
  4. She could ask to be removed from the ranks of the fourth years and “demoted“ to a third year status. (This approach would have been better at the time she moved back to the transactional group to keep the pressure down, but she did not anticipate this problem.)

Kelly‘s dilemma will probably require that she try to find a tutor/mentor/teacher on her own. She can try her law school professors. At least she could start there. Perhaps a recently retired attorney who practiced the same kind of law would be able to help her. She needs a sounding board for her questions and help developing better judgment. This approach has worked for some of my clients with similar problems.

Large law firms would do well to consider an internship system similar to the medical profession where new graduates could learn the basics, ask basic questions of their mentors and teachers, and gain experience without the threat of a negative review.

Is “Do What You Love” Good Advice?

“Do what you love and the rest will follow.”
“Don’t be afraid to follow your dream.”

How often have you heard this advice? It can be an exciting invitation to leave your boring job behind and try something adventurous, daring, and new. There are stories about people who did follow their dreams who landed on their feet. But there are also stories about people who tried to do that and ended up bankrupt or in a bad situation: the actress-to-be who moved to Hollywood, could not get any jobs in the film industry, and ended up waiting tables; the would-be blockbuster author who left the practice of law but did not become the next Scott Turow. One size does not fit all. Good advice for one person is not necessarily good advice for everyone.

thinking womanWhen people give the advice – follow your dream – what they are often encouraging is an entrepreneurial aspiration and a break from traditional work life: the creation of a whole new line of fashion footwear or candle scents or brownies or a new app that will change the world. And sometimes that advice is given by people who are themselves tired of the routine nature of their own lives, and give advice to others that they wish they could follow themselves. The decision to leave your current career path for something that has a low probability of success is something that needs to be thought through very carefully. Sometimes it is the right career move. Sometimes it is not.

What goes into a thoughtful career decision about actually following your dream is a mixture of many elements, including how you will manage risk. The ability to manage risk is both financial and emotional. It includes whether you have enough money in reserve to support yourself if the venture is not an instant success. You want to make a thoughtful assessment of the current economic situation in the world at large and how hungry it might be for your new idea or venture. And there are personality traits that will make a difference in your success. You want to think about your ability to follow through on tasks you give yourself and your ability to face problems and solve them as they arise, as well as your ability to take advantage of opportunities when you see them to push your agenda forward. Do you have responsibilities to your family that will cause you sleepless nights if your venture is not a success? Do you have a lot of debt? This combination of personality traits and economic forces will shape a venture and make it more or less likely that you will realize your dream if you do decide to follow it by taking action. Some people should follow their dream but others should not.

However, even if taking action to follow your dream is not the best advice for you, daring to dream is always good advice. Daring to dream is different from acting on your dream. Daring to dream about what you want in your work life is always very valuable. When you imagine what you really want and need in your dream career, you can learn the building blocks you should have in your actual career.

I ask my clients to imagine a job they would enjoy doing so that we can mine that “dream” for elements that will indicate the right career direction. I ask my clients to “fix” their current job so that we can see what is missing or making them particularly unhappy, and what they yearn to have in a career or a workplace. Once we talk in these terms, we gain a lot of information that is useful for career planning.

Many of my clients imagine a work life where they have a job with a mission shared by other people they respect and who respect them as well. They imagine a collegial group of supportive people, doing work they are very interested in with the opportunity to be challenged and to become an expert, as well as mentoring others. When you dream or envision your career in this way, the specific dream you have that is uniquely your vision becomes very instructive. It guides and defines your aspirational career goal.

Part of the process of dreaming is figuring out your strong interests as well. In fact most of the time I would not say “follow your dream,” but I would say “follow your strong interests.” And if you do not think you have any strong interests, you are probably someone who does have a strong interest, namely, an interest in having a life that allows you time for friends and family and outside activities. Strong interests are important because you want to like what you are thinking about for most of the waking hours of your life. That sounds obvious but I continue to be amazed by the number of people I work with who did not factor their strong interests into their career path choices. I counsel hundreds of unhappy lawyers who do not like thinking about the law. I counsel many new graduates who think they should go into finance or sales because their friends have done that, even though they personally have no interest or aptitude. Interest is a huge motivator. It inspires people to want to get up every day to go to work. Identify your interests and get creative about how to express them in your career. You will be more likely to enjoy your work life if you do.

Not everyone has the ability or chance to follow their strong interests, but even something close or added in your off hours can help to enhance career satisfaction. If you cannot have a career as a musician or author, for example, you might enjoy working with creative people to help them be successful. If you cannot be a sports reporter, you might enjoy writing a blog about sports after hours. If you are a people person and you love making people feel welcome, you might not get to be the host of America’s Got Talent, but you do want to search for jobs where you can have the role of the person who welcomes and embraces others. Maybe that job would be in a restaurant, or perhaps it is in sales, or as part of a hospitality team doing installations and events. When you think about work in this way, mining your dream for the elements that bring you happiness, you can identify the right career path far better.

The key is to dream first. Because buried in your dream are the elements of a work life that you will want to get up and do every day.