Five Steps to Reach Your Career Transition Goal

Last year I was diagnosed with cancer. It was caught early, but I had to go through an operation followed by six weeks of radiation. After that, I had to be on a medication that prevents the further microscopic spread of the cancer, and I have to take hormone suppressant pills for five years.

steps to career success

When I talked with my oncologist about how to stay healthy and active, he told me to increase my aerobic exercise to 30 minutes a day because research has shown that aerobic exercise for at least a half hour every day works almost as well as the medication to prevent a return of this kind of cancer. He also said that the medication makes most people feel tired, but the best way to deal with that is to exercise. “You will have more energy if you exercise,” he promised.

When I heard my doctor say that exercise could prevent a recurrence and counteract the tiredness I already experienced on the medication, I was motivated to find a way to work out every day. But I also know how much I hate aerobic exercise! How could I get myself to work out at least 30 minutes a day and keep it going? I needed to figure out a way to set this goal and keep it.

Now, a year later, I can tell you about what worked, because it did work. And I can hope that these steps will work for you too if you are working on a career transition. Most people hate to network even though they know they need to if they want to transition to a new job or a new career. Here are five steps that helped me and that might help you too.

Step One: Identify a Motivator

If you are interested in or excited about something, use it as a motivator. When I dragged out my elliptical, which had been sitting in a corner of my exercise room getting dusty and generating guilt instead of sweat, I knew that if I set up a playlist of fast and slower music, I had a chance of carrying through a daily routine. The key was the music. I had to like the music and I had to have different tempos so that I would push myself to get my heart rate up but then give myself a break so I wasn’t too exhausted. I searched for good music and downloaded songs I loved. I set up a 30 minute playlist and started with slower beats at first. As time went on, I added faster tempos as I got more accustomed to the pace. I decided that my goal would be to get my heart rate up for the full 30 minutes in the range of 130 beats to 150 beats per minute depending on the song. I was interested to see if I could make that goal a reality.

Step Two: Envision the Activity

There have been many days when I have felt too tired to exercise. But I told myself I had to do it anyway. So I would envision myself on the elliptical and think about how I would move off the couch and get on the equipment. Envisioning myself moving from the couch to the machine and then doing the workout before I did it actually helped me to get going. The same thing is true for your career. When you imagine yourself doing something, if even it is something you do not enjoy, that active imagining can motivate you to get moving on your plan to reach your goal.

Step Three: Coach Yourself or Get a Coach

I would talk to myself and say something encouraging. “All you have to do is get on the elliptical and turn on the music. That is easy. You can do that.” While I was on the elliptical, there were times I was very tired. So my inner coach would say something like,” Look, you are saving your life by doing this! You are getting your heart in better shape so you can dance at your daughter’s wedding.” And sometimes, when I felt really tired, the only thing I could think of to say to myself was, “After you are done with this, you can fall on the floor and sleep. Just finish this and you can collapse.” The inner coach is a big part of your career success too. If you can encourage yourself instead of discouraging yourself, it makes a tremendous difference in your ability to grit it out. Do you need to go back to school to get a degree that makes you more marketable? Do you need to talk with a lot of people to find out the lay of the land and hear about opportunities that might work for you? Talk yourself into it. It is crucial that you have a positive inner voice to keep you going. Sometimes the inner voice might be yelling at you too. Most people need a mix of those two internal coaching voices. Some people get enough from their own positive self-talk. Others need another person to coach them. If you need to hire that help, though, do it. Making a career transition is not easy.

Step Four: Manage Failure

There were days I could not talk myself into exercising. I had to take a pass. I could call myself names because I failed to do what I said I would do, or I could think about it as a challenge for tomorrow and reaffirm my goal for the next day. I tried to make it into a challenge even though I didn’t always succeed in doing that. Managing failure in a career transition is important too. You may have hoped that after many years of working as a paralegal or doing document review, you could find a full time job working as an attorney, but every time you get an interview, it’s for another position doing the same thing you have done before. That can be discouraging. But if you reaffirm an achievable goal and keep at it, getting the additional skills that would help redefine you, or networking more effectively, you will be more likely to transition your career over time. Manage failure by reasserting your intention to get to your goal.

Step Five: Take Baby Steps

When I first began the 30 minute workouts on the elliptical, I started slowly because I wanted to be sure I did not get too discouraged. You use new muscles whenever you start something new. That’s true for your career transition too. If you keep your goal in mind and take small steps in that direction, you have a better chance of being successful. Doing something new uses a different set of skills that you can hone over time. Is it hard for you to have lunch meetings with people and ask them to brainstorm with you? Is it hard to feel comfortable asking for help by saying, “If you were me, who would you want to talk with, and would you be willing to introduce me by email or on LinkedIn so that I can talk with that person?” If that is very hard for you to do, then practice with friends and family before you talk with someone you have never met before. Small steps make it easier to make progress.

Identifying your motivators, envisioning yourself doing what you want to do, training your inner coach, managing failure, and taking small steps in the right direction can help you get to your goal. These strategies helped me get through a tough year and achieve my goal. I hope they help you too.

Get Unstuck from a Low-level Job

Are you stuck in a low paying job? Are you stuck in a job that does not match your need for challenge and development? If so, what can you do to move on?

stuck in a job

When the recession hit in 2009 and in the years that followed, new graduates, full of hope but burdened by debt, entered a job market that offered far fewer jobs than before. When jobs are scarce, people settle for jobs they may not want because they have to pay the bills. They take what they can get. Once in such a job, it can be hard to get out. This is also true of a career path. The path you start out on tends to be the one you stay on unless you affirmatively do something to change your career direction.

What strategies could help you?

Know What You Need

Remember to do your personal assessment first.

  1. What are your strong aptitudes or natural talents?
  2. What are your strong interests in terms of content areas and areas of frequent thought that are enjoyable for you? Are you a people person who loves to talk and connect with others? Are you more intensely interested in video games or problem solving? Do you want to work with your hands and see a finished product?
  3. What do you need in terms of a lifestyle? What amount of money you need to feel secure? What kind of work/life balance do you want?
  4. What do you need in terms of workplace culture?
  5. Knowing these things about yourself, where is the match likely to be good for you in the world of work? Talk with people doing the work you think you want to do and ask them open-ended questions to learn more.
  6. Where are the jobs? What fields are short-handed and looking for help? Often these are the rapidly growing fields. Often you can find them by looking at postings on sites like The Muse, Indeed, and others.

If you do your self-assessment work first, you will be headed in the right direction. My book, Job Quest: How to Become the Insider Who Gets Hired can help you to do this assessment work.

Explore the Value of New Skills and Education

Skills acquisition and a different or a more niched educational degree or certification can often help to reboot a career direction. I know that might mean more debt, and some people cannot afford to take more classes. If you have high student loan debt, going back to school online may be the only feasible option. When it comes to an online reboot of your skills, there are some fields that will accept such credentials, but others that will remain uncertain about the level of expertise you have gained. Wariness about online education is likely to dissipate over time, especially as market demand rises, but it is something to ask about and think about before you spend money and time taking online courses. How will your online education be viewed by a potential employer? Do a cost/benefit analysis.

It might be worth it to spend the money to go to school at an institution that is respected by and closely connected with the industry you want to join. Brick and mortar schools or training camps offer opportunities for creating relationships with professors and students as well as alumni and industry providers. These relationships can be priceless when it comes to finding a good job.

We are seeing good jobs evolve out of the tech revolution; jobs are plentiful for people with the right skillset. Many of these jobs are in new fields such as digital marketing, social media, software engineering, coding, web design, and much more. There are new kinds of institutions that train people for these new career directions and are also designed to open doors to jobs requiring the kinds of skills people need in the 21st century.

One terrific example is the Startup Institute located in Chicago, Boston, and New York. The Startup Institute offers an intense eight week course where you can learn new skills and network with people in the industry. There are also less expensive part-time course options at the Startup Institute where you can learn specific skills such as Javascript or web design. According to their website, 90% of their graduates get jobs in the start-up world after graduating. Their intense course offers web design, web development, tech marketing, sales and account management, introduction to data science, Ruby, and more. Their website says that although the experience “begins as immersion learning with a cohort of strangers – it ends as a network of mentors, entrepreneurs, practitioners and peers that you take with you for the rest of your career.”

That might sound overblown, but I personally know two people who went to the Startup Institute and landed terrific jobs after they finished. The website tag line has proven to be accurate for them.

Startup Institute is not the only option out there. See what you can find.

Don’t let yourself get stuck in a job with no future. Once you know where you want to go next in your career, explore new on-ramps to jobs by investigating educational institutes, boot camps, or local community colleges. Be sure to find some alumni to talk with to be certain that the program is worth the money you will spend to re-direct your career. But once you have a firm basis for trusting the program, take the leap and reboot your career direction. You will be glad you did!

Career 2.0: Finding Your Way to Your Next Career

What can you do to be sure that the new direction you are considering for your career will work out well for you?


There is a clear and simple method you can use to predict career success in your next act.

What are your AIMS?

To figure out the sweet spot for your career, think carefully about four key elements:

First, what are your Aptitudes?
Second, what are your strong Interests?
Third, where is there a Market need match?
Fourth, do you have the Skills you need?

Aptitudes, Interests, Market need and Skills are your AIMS.

Your Aptitudes

Most people who are mid-career have a good idea about what they do well, but sometimes they forget to factor in soft skills or people skills as valuable aptitudes. The ability to engage easily with other people, to read people well, or to draw people out are valuable skills, just as an innate sense of logic or math ability is an aptitude. The ability to stay focused for long periods of time or to predict the next social trend or popular music group constitute aptitudes as well. Make a list of your natural talents and ask close friends and family to add to your list of attributes and natural abilities. You want to shoot for a career that will play to your strengths.

Your Interests

Think of your strong interests as the driver or motivator for your work life. If you can be engaged in work that you enjoy thinking about, you will be happier. There are a number of different varieties of interests that can drive careers in a positive way.

Content area of interest

If all of the books, magazines, TV shows, radio programs, and blogs were available to you right now, what would you reach for first, second, third? What were your favorite classes in school? What are the classes you wish you could take? Think about the experiences you have enjoyed in your life. What you are innately interested in tells you about yourself and can indicate the content you will enjoy if you can have it in your work-life.


Some people enjoy games, gamesmanship, strategy, problem solving, and puzzle solving. Engaging in a particular process and getting better at it can be a motivator in your career and can indicate a good career direction or niche within an industry. If you enjoy process or strategy activities, look for activities in your industry that allow you to engage this intelligence. Whether you are designing events, trials, restaurants, or conferences, you will have fun doing an activity that engages your strong interest.


Some people are strongly goal or achievement oriented. Here the driver or motivator is getting to the finish line or getting a finished product. If that captures your interest, then work that allows you to engage in a project with an end you can be proud of will be a motivator. If it would feel really great to have a finished product – a device you helped to engineer, a bar or restaurant you designed, a construction project you have a hand in – factor that into your decisions about your future career.

Overarching Mission

People who are driven by an overarching mission care about making the world a better place and helping others. If this strong interest gets you up in the morning, you are more likely to be happy in the non-profit realm or another similar mission-driven career.

Other Strong Interests

There are other interests that drive careers as well: a thirst for money (which sometimes also translates to a need for security), a thirst for control, power, fame, or prestige. There are people who love learning for the sake of learning. All of these strong interests can motivate people to achieve in their careers.


If you do not think you have any strong interests, consider this: do you care more than anything about having a life that allows you time with your family and friends and outside interests? If that describes you, then your strong interest is probably a lifestyle or a work-life balance that satisfies your needs. If what you do at work matters less than the opportunity to have a life outside of work, then you need to find work that allows you to have a balanced life.

Market Need

Reality bites. But you have to be pragmatic. If your greatest excitement is something the rest of the world is minimally interested in, your chances for success are slim. If the market wants grilled artisan chicken and you want to give the world a double-fried chicken patty, maybe you better re-think your plan. McDonald’s seems to be learning that lesson the hard way. If you watch trends, follow market needs, and position your new business venture in the mainstream of the public’s felt needs, your business should do reasonably well. If you are a seer and you can predict where the market has an unmet need, you might be able to ride the crest of a wave that is coming. Try to minimize risk if you can when you start your new venture or move into your new career by assessing market need.

Skills Match

Do you have the skills and credentials to make this transition a success? I am sometimes surprised by the way my clients in transition think about the skill set issue. They tell me they know that they could so this new job even though they do not have the requisite experience, credentials, or acquired skills. It’s true that the professionals I work with often could make a major transition to a new field and do well because they are smart, capable, and quick learners. That’s not the problem. The problem is one of perception and willingness of people in the new field to accept someone without the requisite skill set. Just because you really could do this new job doesn’t mean the world will let you do it. Be sure your skills match up with the needs of the job.

When you satisfy all four elements: Aptitude, Interest, Market need, and Skills match, you are aiming in the right direction and you will be happy with your career transition.

How to Transition Out of the Law or Into a New Practice Area

“I am fed up with being an attorney. I want to know what else I can do with my life!” Those are words I often hear when lawyers begin career counseling work with me.

leaving the law

Lawyers decide to explore options outside of the law for many reasons. Some attorneys are burned out by stressful environments and a lack of control over their hours. Others have been worn down or damaged by interactions with negative or overly critical partners or others in their workplaces. Still others have chosen a profession that does not play to their strengths. Some of the people I counsel would be unhappy in any profession, often because they carry psychological baggage that weighs them down.

Wanting to leave the law does not mean that you are actually going to get out. When you attempt to move into a non-legal field, you can expect to be viewed skeptically. You often need to make a pretty convincing case for yourself. Potential employers are bound to think that you may be taking a vacation from the law but that you will return to legal practice as soon as you find an opportunity that pays more. Other employers will wonder about your ability to get along with co-workers and supervisors. Some employers will question your ability to remain loyal to their workplace. Employers may reject you because of what they assume to be your monetary expectations. Still others will make assumptions about how argumentative or arrogant you are likely to be, simply because they believe lawyers have those traits.

Many non-attorneys continue to have an idealized view of legal practice. These people cannot understand why you would want to leave the law. Lawyers leaving the profession usually need to do a convincing job of explaining their seemingly aberrant behavior to people who do not understand the stresses and strains of the legal work world.

Despite these barriers to transition, I have successfully counseled many attorneys who decided to leave the law. Who gets out? Why are some lawyers successful when there are many who have the intention of leaving but do not accomplish that goal? There are five key factors I have learned to assess to predict a lawyer’s successful transition from the law.

These factors are: 1) the carrot, 2) the stick, 3) grit, 4) economic reality, and 5) the ability to engage in rapid relationship and trust building.

1) The Carrot

One of the most important factors to assess is the “carrot.” What are your needs? What draws you away from the practice of law and how deeply does it excite your interest? If you are profoundly interested in a pursuit outside of the law, especially if it is a long-standing interest or a mission you believe has importance and meaning for you, it is more likely that you will realize your goal of leaving the legal profession.

Sometimes I ask clients to tell me what they envision themselves doing other than the law, or I ask them to tell me about someone who has the job they think they would like to have. I ask these questions to assess the “carrots.”

There might be a strong interest or passion that has been buried under a pile of “shoulds.” “I should be a lawyer because I can make money doing that. But I wish I could develop this idea I have for an app that I know would be very popular.” “I know I ought to stay in the law because I can have a secure job, but I would love to be a broadcast journalist.” I have worked with attorneys who had these dreams and successfully transitioned their careers. In each case, the attorney had reason to believe that she would be successful before fully leaving the field of law.

There have been many other attorneys who made transitions out of the law or into non-legal jobs where a JD was either preferred or at least not a barrier to transition. Some of my clients have successfully left the law to move into financial planning, compliance, strategic communications, sales for a variety of services for lawyers, professional development, career services, and many more fields. In each case we looked for the “carrots.” People who need work/life balance or a collegial team, work that ends at the end of the day, or a mission of making the world a better place can find these and other “carrots” in non-legal jobs or other settings within the legal field. The “carrots” guide them to jobs that are better matches for their personalities.

2) The Stick

Another important factor is the “stick.” The stick is whatever it is you are trying to get away from in your work world. Your stick might be a difficult partner, the stress of trial work, demanding clients, or a poisonous work environment. When the stick has to do with the way you are practicing law, it tells me that you will probably need to modify or leave your present workplace, but it does not necessarily mean that you will be happier with a divorce from legal practice.

But what if you never liked the practice of law at all? What if you became an attorney to please your parents, for example? Many attorneys enter the field because they are urged to do so by well-meaning significant people in their lives. Some of these “helpful” people may have dreamed of being lawyers themselves, but could not fulfill those dreams. What if you are living out someone else’s dream? That is a stick with greater weight. If you are truly uninterested in the content of the law, modifying your workplace will not enhance your satisfaction because you still have to spend a lot of time thinking about content areas that are uninteresting to you. You are more likely to have the degree of motivation you will need to successfully leave the law.

3) Grit

Next, there are a group of personality traits that indicate you have the motivation and tenacity to make a career transition. Tristan Jones embodies these traits. Tristan Jones was a British sailor who was crippled in World War I with a back injury and was not expected to walk again. Not only did he make a remarkable self-motivated recovery, but he went on to become a solo sailor. He sailed around the world with his one-eyed dog and wrote books about his adventures. At one point he decided to sail his boat on the lowest and highest (altitude) bodies of water on earth: the Dead Sea and Lake Titicaca. He had to figure out ways to transport his boat, get past surly customs officials, deal with dreadful weather, insects, sickness, boat repair, and a host of other seemingly insurmountable problems. In his book, The lncredible Journey, he tells the story of his travels, which he accomplished without the assistance of financial benefactors.

Jones’ determination and tenacity were remarkable. But in addition to those traits, he gets high marks for initiative, creativity, flexibility, endurance, and perseverance. These are the ingredients that compose what you might call the “Tristan Jones factor,” or you could call it “grit.” How hard will you work to accomplish your goal? Fortunately, you do not have to be as determined as Tristan Jones in order to leave the law, but these traits are the ones that will help you to make a successful move.

4) Economic Reality

Another factor that must be assessed is your economic situation. Dan had been building a successful practice for over 15 years, but his interest in the law had plateaued. Bright, creative, and restless, Dan was fed up with “a life of bickering in court.” Before becoming an attorney, he had wanted to do free-lance writing, but his family had discouraged him from pursuing that path. When his best friend died of a heart attack at 51, Dan felt the pressure of time for himself. He burned to leave the law to become the free-lance writer he had always dreamed of becoming.

The problem was that he had a wife and three college-bound children who were accustomed to an affluent lifestyle. Even if Dan were willing to make a radical change in his lifestyle and live on far less income, his family was not. We spent time exploring, evaluating, and ranking his priorities. Although his first personal priority was to become a writer, he had an even higher-ranking priority, which was to maintain and support his family. Before doing that analysis, Dan had felt angry about being pushed by others to continue to practice law. After our counseling work Dan felt that he chose to continue to work as a lawyer to support his family, at least for a period of time.

Dan decided that his short term goal was to do as much free-lance writing as possible. He negotiated an “of counsel” arrangement with his firm, cut back on his work hours, and sold their second home to help finance his reduced work-schedule. His long-term goal was to leave the law. Once Dan acted on his plan, he felt relieved and his legal work life became more satisfying. Dan is less certain at this point that he wants to leave the law altogether. He has achieved a sense of balance in his life that is gratifying and permits economic stability.

5) Effective Opportunity Development

The last key piece to a successful career transition has to do with understanding and utilizing information about how to effectively develop opportunities and jobs. This is often called networking, but I prefer to have my clients think about this process in a different way. Instead of “networking” I teach them how to go on a quest using a medieval quest analogy, where they have a clear idea about their mission, which is to find some of the wizards and knights in this realm/ industry/ field and get creative about how to meet them.

It is important to be prepared to have well-scripted, small vetting meetings with multiple people in the industry they are trying to move into. These meetings are what I term “rapid relationship and trust building.” The goal is to become known and trusted by people who are already in the industry; this is an effective way to become the “insider who gets hired.” Such an approach opens doors and develops potential jobs and other opportunities for the job-seeker. But the messaging matters. You cannot ask someone for a job first thing because that limits the amount of intelligence you will gain.

The focus is on learning about the industry and learning gossip, hearing rumors, developing knowledge about what is happening on-the-ground, finding people already doing the work you would like to be doing, and learning from them. The focus is also on doing research so that you know the places where your skills could be useful and valuable, and articulating your value in these vetting meetings. Since more magic happens in person, I teach my clients how to engineer their luck by identifying people who are well positioned in the field and understanding how to connect with them in person if possible. This process includes giving back to people who help and guide them. These ideas and scripts are in my book, Job Quest: How to Become the Insider Who Gets Hired.


Transition out of the law is not easy but you can do it. You just need to know what to do and have the tenacity and motivation to work your way to your second life.

What Does It Take for You to Make a Change?

Do you have trouble getting yourself to adopt a new habit even when you know it is good for you? You are told you need to stop smoking, but even though you have the best intentions you cannot carry through. You want to stay on a weight loss program or make it a habit to exercise every other day, but it just isn’t happening. You want to change your career and you have worn out your friends and family complaining about it, but you cannot take the steps you need to take. If creating new habits is a problem for you, you have a lot of company.

In her new book, Better than Before: Mastering the Habits of Our Everyday Lives, Gretchen Rubin, a former law clerk for Justice Sandra Day O’Connor, puts the spotlight on personal habit change and identifies four very distinct groups of people who have innately different approaches to change. Her categories can help people understand themselves better, which could lead them to finally make the habit changes they want to make.

people in groupsRubin says there are four basic types of people: Upholders, Questioners, Obligers, and Rebels. Upholders respond to outer or inner expectations. They can give themselves an order and they will carry through. If an order comes from an external source, they can also carry through. Questioners question expectations. They will only carry through if they adopt the order and internalize it, and make it their own. Once they do adopt it, they will carry through. Obligers can meet outer expectations but have trouble with inner expectations. This means that if the directive comes from a teacher or a boss or a coach, they will do it. But if the expectation is one they set for themselves, they struggle with it. Rubin speculates that Obligers are by far the largest group of people out there, which explains why so many people have difficulty changing their habits. When it comes to the Rebels, change that is ordered or even suggested by others triggers their opposition. The more they are told to do something, the more they resist. Rebels will fight changes they should make, or reject helpful suggestions.

I often counsel people who have longed to change their careers but have not made it happen. Part of the problem is that they do not know how to identify the right career direction. When career changers come to work with me, we first figure out the right direction. We identify the building blocks of their personality (what they need to have and need to avoid in their careers to be happy) and match that with current or potential skills and market need to see where they could move their careers to become happier in their professional lives. The process works well to identify the career direction, but then the person has to be able to follow through and take steps to make the necessary changes in his or her life. I can provide information and support, but I cannot make anyone change.

Rubin’s concepts are helpful to me as a career coach. I have worked with some people who are Rebels, others who are Questioners, some Upholders, and many more Obligers. Before learning these ideas I did not have a name for the problem that I saw being enacted by many people who earnestly wanted career transitions but could not follow through to make the necessary changes to achieve their goals. Now I realize that Obligers need more clear directives from me.

But I also believe that once people recognize their habit tendency group, they’ll able to work more effectively to make change happen. For example, Obligers can create change if they give themselves homework and write down directives as though the directives were coming from an external source. I know this is possible, because I am an Obliger who has turned into an Upholder. I’ve taught myself to follow my own orders by assigning them to myself as though they were homework. If you know you are a Questioner, you might shorten the time you question because you understand this is a way you put off change. Rebels who know they are rebels might be able to talk themselves into being more open-minded if they understand how valuable that attitude shift could be.

Do you recognize yourself? What is keeping you from making the changes you want to make in your life? What will you do to change the way you think about meeting expectations?