The first step in the job search series is knowing what you want to do. For some people this is easy (I’m looking at you “lifers” out there, aka doctors, lawyers, tradesmen, etc.) For the rest of us, there is a lot more ambiguity, which can be both good and bad. I’ve had times where I wasn’t sure what to do next, and you may have too.

Fortunately, there are things we can do to help pinpoint what we may be good at and may want to do next. Below are a few exercises that can help you decide what to do next

Exercise #1: “Top 3”

This exercise is designed to help you look for situations and patterns that tee you up for success or tee you up for failure. I’ve always loved this exercise and use it for myself.

• First, look back and name 3 times you were “in the groove” professionally and were extremely happy. Be as specific as you can, then unpack who, what, where, when, why, and all that good stuff. Skills used, etc. Then look for similarities.
  1. For example, who did you work with? Were you on a team or alone? If on a team, how many people were on it? Did you manage others or were you an individual contributor reporting to someone else?
  2. What were you doing? Were you working on something new and unknown, or improving something existing? Did you have clear requirements, or did you have to figure things out on your own? Did you have a time limit, or was the focus on the best possible outcome?
  3. Where did this happen? Were you in an office, working from home, sitting at a coffee shop, doing an internship in college, etc? If at an office, what was the attire for that place, and what was the office like (stuffy, everyone in a suit, or open office with ping pong tables and people bringing their dogs to work)?
  4. When was this? The year doesn’t matter, but the time might. For example, are most of your “winning” things happening in the morning, or right after lunch, etc.? This will tell you what windows of time are most important to you, and you can build that into your next job.
  5. Why you do something matters to some people, and doesn’t matter to others. Do you do your best work when you believe in a cause and feel passionately about what you’re doing?
  6. What skills did you need to in these scenarios? Are those skills you enjoying using the most? Are they skills that most people don’t naturally have? Those are your strengths, and are things we want to look for in future jobs.

• Next, name 3 specific times you were miserable and unhappy or totally failed professionally, then do the same exercise as above
• Then, put it all together and you’ll come to a good idea of what things set you up to do well and what things prime you for failure. Obviously, you want a job that puts you in a place to succeed and has situations that will deliver on those things you respond to best to.

As I mentioned before, doing these exercises for myself has always been useful, and here is what I found out about myself in doing it:

• I do best when I work in groups that have autonomy and are tied to people that have decision-making power and the ability to get things done quickly (usually the C-suite for me). I enjoy working where I have frequent engagement with other people but can go heads down when needed. I don’t seek to manage others, but when I do I am more “hands off,” valuing people that I can trust to solve regular issues and don’t need to be micromanaged. My best times are first thing in the morning and, unfortunately for my wife and dinner with my kids, right around 4:45-6pm. Projects I most enjoy are ones that are technically and intellectually challenging and don’t have existing solutions or need significant work, with many unknowns. Because I enjoy these challenging types of projects, my productivity can require longer windows of uninterrupted time, so a day punctuated with many meetings makes me unproductive. The skills I gravitate towards are distilling complex things into smaller pieces and teaching them to others. I also love to “create” in some form or another, whether that means building new products, websites, software, etc. The quickest way to set me up for failure is to put me in an office where I have no one to talk to or work with and to give me a task that is routine and intellectually “boring,” requiring little thought. I also do best when I have someone be organized for me, as that isn’t my A+ strength.

Exercise #2: “Skill Inventory”

 This exercise is meant to help you narrow in on the skills you have and don’t have. To be most successful, you want to work somewhere where you can use your “A” strengths over and over again, while letting someone else handle things that are your “C” or “D” strengths.

 Here’s how you do it:

1. Using the examples listed in the Top 3 exercise above, list the skills present (or absent) from each of the examples you gave, then give yourself a letter grade for each of those skills (A+, A, A-, B, C, D+, etc.)
2. You can also evaluate yourself for other skills from the following list, or any others you want to add that are specific to the types of jobs you may end up doing:
   • Attention to detail
   • Good with people
   • Ability to explain difficult things
   • Focus
   • Motivation
   • Openness to change
   • Creativity, etc.
   • Technical skills (for certain jobs things like MS office, or SQL, etc.)
   • Job specific skills (welding, debt finance expertise, etc.)
3. Takeaway: you want a job where you can hit on your “A” strengths over and over and over again, and pass off your “C, D, and F” strengths to someone else who has those things as their “A” strength. My marriage is like this, and it really helps and makes things enjoyable.

Exercise 3: “Dream Job” Dreaming

Another fun one asking a similar question from a different angle. Think of and list your “ideal” jobs, or top 3-5. These are dream jobs, so don’t worry about whether or not you are “qualified” for these jobs or whether they pay enough; this is more about looking for characteristics that attract you, or that you may subconsciously look for in a job.

1. Just like the “Top 3” exercise, unpack what it is about those jobs that jump out to you the most. What do you love about them? What’s a common thing in them?
2. Example: here are a few jobs I’ve always thought would be amazing:
   • Motivational speaker / author / personal coach – hey look, I’m starting on this in a small way!
   • Tour guide taking travelers into the wilderness and helping them enjoy the beauty of nature (I actually have an early plan for this that involves another passion of mine too but I’m keeping that under wraps for now!)
   • Designing and building yachts

Now, those may seem kind of eclectic, but there are a number of things they have in common:

1. Appreciation for nature or being outdoors, ideally ways to help people connect and find renewal and rejuvenation
2. A desire to “teach” and help others improve themselves, or learn about what interests them
3. An inclination to take things are simply an “idea” or an unstructured dream and turn that into a reality. In other words, I love to and want to “create,” whether that is software products, boats, growth in people or their careers, etc.

Final exercise: if you don’t know where else to start, take career assessment or personality tests

This may sound funny to you, and you may not have taken a career test since high school, but assessments like these are great for a few reasons:

1. These generally are consistent for years at a time, so they can be helpful for unpacking things you are drawn towards and care about most.
2. They also suggest specific careers that may be a good fit for you, which the other exercises don’t (obviously some may require special training or education, but this assumes you would go ahead and get those)

There’s a self-assessment by Pfeiffer called “Career Anchors” that I had in the past, I’ve done the DISC assessment, and then there was one I really liked called “Career Leader” that was an assessment we did and that gave sample careers you may be interested in. The Career Leader one is great because it looks at your:

1. Interests
2. Skills
3. Motivators

And then looks for where those would be a good fit in terms of careers and company culture. Note: I’m not being paid in any way for mentioning them.

Wrapping up

You have a number of exercises you can do to help you narrow down what types of jobs would be good for you. While most of these exercises don’t give specifics for a career, they give you plenty of things to look for in a future career, leading to informed decision making and more informed interview questions as well.