(30–60 Minutes)

It may sound odd to have to go through an exercise to identify your preferences. Most of the time, you just know what you like. Take food, for example – I know I love pizza, burgers, Peking duck, and foie gras (damn it, why can't I be one of those people that likes vegetables or more healthy foods?!). When it comes to working out, I love going on a nice long run and doing push-ups, but I really don't like doing pull-ups.

With work, what we like gets a lot murkier. We often find ourselves struggling to reconcile a number of conflicting external influences. There are our parents, who understandably want their children to be able to support themselves by earning reliable incomes, which impacts the ideas and values they impart. Then there are the messages we hear on TV and in movies, which often glamorize less stable career paths. And then, of course, our peers may be influencing us with their own beliefs about money and careers. No wonder it can be tough to know whether you really like a job, on your own accord. That's why you'll be going through some exercises to help you cut through all that noise, so you can confirm what you genuinely like.

Either on a piece of paper or using your favorite computer tool (e.g., Word, Excel), list all of the jobs you've had since high school, and the approximate dates you held each job. If you've had hobbies, class projects, or other extracurricular activities that took up a meaningful amount of time, put those on your list as well. Under each role, write a couple of sentences about what you liked about the job or role and what you didn't like so much. Try to be as specific as possible about the good and bad aspects.

Some factors that could help jumpstart your brainstorming include:

• Schedule: Flexible or rigid
• Work Hours: Not much, average, or a lot
• Predictability: Proactive or reactive
• Stress Level: Low, medium, or high
• How You Were Managed: Micromanaged or full autonomy
• Managing: Individual contributor or manager
• Work with Others: Independent or team-based work

(30–60 Minutes)

“What is your competitive advantage?” asked Aaron.

My friend wasn't trying to be brash. His question came up as part of an informal coffee chat I had set up when I was thinking about changing industries from investment banking. I wanted to meet with Aaron, who had worked in private equity for several years, to learn more about the industry and find out if my background would be an attractive fit.

During our conversation, Aaron was trying to better understand what unique skills I had that would motivate him or a recruiter to choose me for a position over someone who had the exact background the company was seeking. While I wasn't able to dazzle Aaron with my non-answer, his questioning did make me realize I needed to be able to answer this question not only for interviews, but for myself as well.

To figure out how you're smarter, faster, or better, you'll first have to identify what you're good at. Refer back to the list of jobs, hobbies, class projects, and other extracurricular activities you developed in Exercise 1 and then add two rows below each activity: “What I Was Good At” and “What I Struggled With.” For each role, write down what activities or parts of your job you were especially good at, or not so good at:

• Did any particular projects stick out?
• Did you earn recognition for any accomplishments?
• Did you often receive praise for certain skills or qualities?

After completing this exercise, review the activities and projects you noted under “What I Was Good At,” and categorize them by type of interest or skill. Take note of any skills and interests that you discover before moving on. Here are some examples of categories to help you get started:

• Communication Skills: Write clear emails, communicate effectively internally and externally, develop engaging presentations, public speaking
• Self-Management: Hard-working, diligent, self-motivated, organized, proactive, efficient
• Leadership: Lead projects, speak up in meetings, suggest new projects or improvements to existing processes, help new or more junior co-workers
• Interpersonal Skills: Work well with internal and external stakeholders
• Flexibility: Ability to work under pressure, ability to adjust to changing priorities, able to work with little direction
• Computer Skills: Word processing, creating presentations, developing models, creating programs

(30–60 Minutes)

How do you spend your time outside of work? On your existing piece of paper or computer file, write down topics or subject areas you read about or listen to in your free time, whether via books, articles, blogs, podcasts, or videos. Do you see any common themes surrounding your interests?

For example, long before I became a financial planner, I would read about personal finance, real estate, and credit card hacking in my spare time. These topics interested me from both an intellectual and a practical perspective. As my knowledge level became more advanced, I began listening to personal finance podcasts on the subway. I'd regularly get into conversations about finance and real estate topics with anyone who was interested. Eventually, I began writing about personal finance topics on my blog. I even took vacation days to attend personal finance conferences (what a nerd!).

(30 Minutes)

While reviewing your past experiences and current interests is a great start to figuring out what you like and what you're good at, sometimes talking to others can help you confirm what you already know or identify skills and interests you didn't even know you had. For this exercise, reach out to friends, co-workers (past and present), and family to help identify and confirm your skills and interests:

• Do people often reach out to you with particular questions?
• Do people frequently ask you for help on certain problems or projects?

I found this step to be especially helpful, and was able to identify several skills and interest areas that I had never thought of myself. For example, multiple friends told me I was really good at finding deals and optimizing my time – things I just assumed everyone was good at. A colleague said I had a talent for developing Excel models to help people make important life decisions – another skill that I had thought wasn't really unique to me. And my wife, Jennifer, specifically told me she thought I would be a great financial advisor.

It's easy now to look back and realize that becoming a financial planner was an obvious path. But in the moment, I thought that financial planning was a career for people who couldn't get into investment banking, and that the role just involved selling financial products. So my response to Jennifer in the moment was a firm no. Eight years later, here I am, writing to you as a proud financial planner.

(30–60 Minutes)

Many work and personality tests are available to help you further uncover your interests and strengths, including the Myers-Briggs, StrengthsFinders, and DISC tests (all of which I have taken, and recommend). While these tests may not perfectly describe your personality or preferences, taken together with your past experiences and feedback from others, they can help confirm your interests and skills. Tests range in cost from $0 to $75, on average.

(30–60 Minutes)

One factor that I never took into account when considering my first job out of college was my desired lifestyle. That may have been because my classmates and I assumed college business majors had two career choices: investment banking or consulting. Since both routes required long work days and/or frequent travel, I thought having a stressful work experience was inevitable.

Seven years later, when I was contemplating leaving the investment banking industry for good, I was much more deliberate about ensuring that the next job I pursued met my lifestyle needs. By this point, I had a sense that many roles could align well with any particular set of skills and interests. I had also learned firsthand that regardless of how well you are doing professionally and financially, if your job prevents you from having the lifestyle you want, you likely aren't going to be happy. That's why this next exercise will focus on helping you determine what type of lifestyle is right for you.

(20–30 Minutes)

There are always consequences and trade-offs when you make decisions about how to allocate time between your personal and professional lives. The following questions focus on what work-life trade-offs you may be willing to make. Take your time formulating your responses; they may require quite a bit of thought:

• How flexible are you on a specific city or location? If you could make more money in a location other than your ideal location, would you make that trade-off? If so, how much more money would you have to earn?
• Are you willing to work in a high-pressure job that requires you to work evenings, and sometimes weekends? Would you be willing to be on call or available to your team 24/7? How much of a salary increase would you need to make this trade-off?
• How often are you willing to travel in a job? Are you willing to travel most weekdays, like a typical consultant, or do you prefer not to travel at all? Would money play a role in the amount of time you were willing to travel?
• Is it important to you to eat dinner at home every night, whether alone or with your family (pets included!)?