A Four-Step Plan to Figuring Out What to do With Your Life: How to Get Un-Stuck, Un-Bored, and on Your Way

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The Problem

While catching up with a friend of mine the other day (We’ll call her Kira), she lamented (as so many of us in our late 20s and 30s do) that she felt confused and torn about what to do with her life.

Despite the fact that she’s about to graduate with an advanced degree from a top school and has plenty of professional connections, Kira is neither excited about her prospective career options, nor has she been able to come up with any better alternatives. “I feel badly complaining about it, because I know there are worse things to deal with, but I feel kind of bored and stuck . . . or maybe I’m just lazy . . .” she finally confessed.

Yeah, yeah, yeah—Kira is privileged (which at least she’s self-aware enough to recognize . . .) and, in general, is dealing with one of the more preferable of life’s challenges: being flush with options, but lacking a sense of direction (or motivation).

Nevertheless, her story is a pretty common one: you start a career, and maybe do some post-baccalaureate or graduate training, and you’re a few years in—finally having some time to reflect and even coast a little—when you realize that you’re feeling “off-path,” “off-center,” and like you’re maybe/possibly/definitely headed in the wrong direction. . . .

You begin to recognize that the current state of the world feels wrong, but have no flipping idea what to do to set it right, and the more you think about it, the more you stress and fret about making the wrong move—you’re no longer 22—decisions you make now matter! (Yada, yada . . .).

The reality is that tons of people go through this and it’s totally normal—and in my opinion, it may even signal some high level of self-reflection and thoughtfulness, and a desire to always question the status quo—all of which are good!

A Workable Solution

So, first things first, stop wallowing and beating yourself up, recognize the privileged position you’re in (i.e., Having options is more than most people in the world have, and if you’re still feeling bad for yourself, try this), and get ready to deal with your semi-existential crisis head on as I walk you through the 4 basic steps that I shared with Kira to figuring out what to do with your life . . .

Materials Needed

  • A few sheets of paper or a notebook
  • A pen or pencil (Yep, I recommended doing this process by hand versus on the computer; in my experience, something about the brainwaves-to-pen-to-paper process seems to make it work better for most people.)

Step 1: Do Some Self-Exploration.

Get your pen and paper out, and get cozy—you may be here for a while.

When you’re ready, I want you to write down your top 25 accomplishments in life—things that you succeeded at and that you enjoyed doing.

Identifying all 25 might take a few days, so feel free to carry a notepad around to use as necessary, or email yourself a note from your phone when you think of an item to add to your list—just be sure to get the email correct. (Poor Daniel Harlan gets so many of these from me . . .)

Once you have 25 items on your list, narrow it down to your top seven (and, no, you can’t just start with seven—you must have a list of 25 and narrow it down to seven). Now take a look at these seven: Underline, highlight, or circle anything that stands out or strikes you as interesting.

When you’ve got your final list, take 10 minutes to answer the following questions:

  • What values can you do you see as important to you, based on these stories? (e.g., I value moral courage!)
  • What character strengths do you see in yourself, based on these stories? (e.g., I’m persistent!)
  • What are your technical skills, or the things you’ve learned to do—like data analysis or computer coding—based on these stories? (e.g., I’m good at teaching!)
  • What interests or passions do you have, based on these stories? (e.g., I’m passionate about helping others!)
  • What work conditions (environment, people, etc.) are important to you, based on these stories? (e.g., I like a flexible work schedule!)
  • How have your accomplishments had a positive impact on others or on the world? Be generous and supportive of yourself here; list anything that even slightly benefits someone other than yourself—no matter how small (e.g., I helped a child understand how to convert fractions to decimals, I showed that girls can be competitive athletes, I bring humor to the work place, I rescued a cat . . .).

While you’re at it, don’t stress too much about getting the categories right here (e.g., maybe you list the same thing as a strength and a value—totally fine); the important thing is that you’re beginning to hone in on your ideal, authentic, and most purpose-driven identity.

Based on your answers to these questions, can you identify any common patterns in terms of the skills you used, your motivations, your work environment, your roles, your colleagues, the impact you had, the type of task?


Step 2: Identify the Activities That are Best Suited to Your Unique Identity.

Take a look at the notes that you took in Step 1 about your values, strengths, skills, interests or passions, ideal working conditions, and contributions to others. Which are most important to you on a gut-level? Which ones give you a sense of purpose?

(Hint: Research suggests that identifying what gives you a sense of purpose, even if you have to experiment a little, is critical to long-term fulfillment, so don’t skimp on this part . . .)

What activities, roles, or jobs would allow you to do all, most, or some of the important items from your list?

WRITE THESE DOWN. Don’t worry too much about whether you want to make a career out of them—we’ll get to that later.

Here’s an example from a friend of mine:

Responses from Step 1:

  • I’m good at acting/entertaining/dancing.
  • I love English!
  • Helping others is important to me.
  • I value autonomy/flexibility, but also like collaboration.
  • I’m organized.
  • I like working with others.
  • I want flexibility in my life and don’t want to work in an office.
  • I enjoy contributing by supporting others.

Here’s a selection of activities that he listed for Step 2:

  • Be an actor. Join a community theater. Teach acting.
  • Be an actor/waiter.
  • Be a teacher. Teach English. Tutor in English.
  • Be a personal assistant and help people get organized.
  • Write a book.
  • Be an editor. Be a freelance editor (work from home).

If you’re struggling to identify your options here, try the following:

Do a few informational interviews. Think about people who do things that sound interesting to you. Drop them a line and ask if you can meet them for coffee (or eat a bunch of caramels) and ask them about what they do. ProTip: make a list of questions to ask beforehand or these conversations can be awkward and a waste of everyone’s time.

Do some volunteer work. A good friend of mine is a sales manager, but is interested in working with animals (a passion that she’s harbored for several decades now…). Since she’s not 100% sure this is the right career for her, she’s sticking with her day job for now, but testing the waters with a volunteer gig at a local animal shelter. If all goes well, she may very well make the leap—or maybe she’ll stick with her retail job and get her fill of working with animals on the side (a totally fine option, as long as she feels like she’s fulfilling her purpose and doing activities that honor her values, skills, preferences, needs, etc.).

Join a local group/club that sounds interesting or fun. Join Toastmasters to brush up on your public speaking skills, try intramural soccer, join the school board, or start a book club. If you don’t know where to start, check out your local options on MeetUp.

Take a career-related personal development course or assessment. You can take these from a career coach (I’m thinking of offering a 2-day workshop on this for Bay Area folks, so contact me if you’re interested), through a connection with your college alumni career center, or for free online. (This one is pretty good.)

Step 3: Determine How to Incorporate These Activities Into Your Everyday Life.

Okay, so you’ve figured out who you are (I mean—the basics….), and what kinds of activities honor this identity (at least a short list. . .). Now it’s time to think about how to incorporate these activities into your everyday life.

There’s no one best way to approach this—and so much depends on your context and situation (e.g., which of these activities you already do, how flexible you are re: changing jobs/careers, whether you want to explore an activity more or make the leap toward doing it regularly), but here are a few questions to help you as you explore your options:

  • Which of the activities on your list do you already do on a regular basis—either at your job, through your hobbies, as a volunteer, or in your personal life? Kudos to you—however lost you may feel, at least you’re incorporating some aspects of your true identity into whatever you’re currently doing.
  • Which other activities do you want to explore or do more of?
  • Which activity seems to “pull” you the most based on your research from Step 2? (Hint: if nothing pulls you, then go back to Step 1 and/or Step 2. When you hit on the right activity or activities, you’ll feel a physical reaction in your body—usually in the stomach or heart, but sometimes in your head; you’ll know when it happens.)
  • Does this activity involve a job or career change or can you incorporate it into your life as a hobby or a tweak to your current job/path (e.g., talking with your boss about taking on more management responsibility, working from home, leading a training)?

If you think it’s more of a tweak or an add-on, then DO IT NOW (e.g., sign up for the race, invite your friends over for dinner, call the local community center about being a volunteer, make an appointment to talk with your boss, etc.).

If you think that it may necessitate a job or career change, then consider your certainty around how fulfilling this activity will actually be. Is it likely to increase your happiness, give you a greater sense of meaning, something else that’s important to you?

Here’s the rule of thumb:

  • high certainty about fulfillment potential = consider a big change
  • low certainty about fulfillment potential = do more exploration

If you need to spend more time exploring (which is fine and even good!), go back to the exercises listed in Step 2. If you’re ready to implement, then take a deep breath, talk to anyone that you need to talk to (like your partner or spouse—especially if it impacts them), make the necessary preparations, and take the leap!

Now for some obligatory advice on quitting your day job:

If after getting this far, you’re pretty sure that it’s time to move on from your current job or career path, consider whether you want to take the leap now (Are you financially and emotionally prepared? What’s your back up plan?), or whether it may be better to ease your way into this by remaining in your current position, but exploring other options (networking, informational interviewing, volunteering, etc.)? Consider the plusses and minuses of both options. (If you can’t identify plusses and minuses for both of these options, then you’re not ready to make the leap.)

Also, consider whether you really need or want to change your job or career. I have a friend who’s passionate about both social science and clowning (You can’t make this stuff up…), so she’s a college professor by day and does clowning after classes—unconventional, but it works for her!

Step 4: Reflect, Adapt, and Change Course as Necessary.

Perhaps the most important and hardest part of this whole process is recognizing that getting it right is going to take some time and energy—which is exactly why so few people actually get it right—nothing worth having comes easy, and many people give up when things get tough.

The point is not to figure this all out in a day or a week (however much I wish it worked this way…), but to be thoughtful and reflective and to LEARN from your experiences. Explore what works better or worse and adjust your behavior and actions as you go.

In the long run, if you are relentless about keepin’ on keepin’ on, you’ll eventually find your right path and end up where you’re meant to be. If you’re lucky, though, this too will change and shift over time as you grow and change and get to know yourself better, so you’ll likely need to revisit the steps listed in this guide more than once, which you shouldn’t feel at all badly about.

Good luck and leave your comments below to let us know how it’s going, or to share any tips that you pick up along the way, and as Liz Gilbert would say, “Attraversiamo!”

Keywords: leadership, personal development, career, fulfillment, happiness

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