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

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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Editor’s Note:

Due to the overwhelming popularity of this post, we’ve developed a free workbook version that includes the content below, as well as some extras to help you along the way. You can access your complimentary copy, and become a part of our community, by signing up for our newsletter.

You will also find this and similar exercises and activities in our book The New Alpha: Join the Rising Movement of Influencers and Changemakers Who are Redefining Leadership. (If you like this blog post, chances are, you’ll love the book, which is similar, but much more comprehensive.)


Tell me, what is it you plan to do with your one wild and precious life?

~Mary Oliver


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:


  1. 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.
  1. Which other activities do you want to explore or do more of?
  1. 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.)
  1. 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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Danielle Harlan is the Founder and CEO of the Center for Advancing Leadership and Human Potential (www.leadershipandhumanpotential.com) and author of the leadership book, The New Alpha (amzn.to/29C0V6j). She earned her doctorate in political science and M.A. in education from Stanford University, where she was a Jacob K. Javits National Fellow and received a Centennial Teaching Award for excellence in instruction. Prior to launching the Center, she was the Chief of Operations for the Carnegie Foundation, where she worked to harness the power of networks and quality improvement strategies in order to solve important educational problems. Named one of Silicon Valley's "40 Under 40," Danielle has also been a speaker for TEDx and worked as an instructor at the Stanford Graduate School of Business and U.C. Berkeley Extension's Corporate and Professional Development Program. In addition, she has given guest lectures at the Hasso Plattner Institute of Design (the “d.school”) and the Career Development Center at Stanford, and has been featured in leading publications such as Fast Company, Forbes, and Women's Health. Danielle started her career as a Teach For America corps member and later served as a mentor and advisor for Global Leadership Adventures, an international leadership development and service program. In addition to teaching in the U.S., she has taught in Brazil, China, Costa Rica, and South Africa. She is a member of the International Leadership Association, the Association for Practical and Professional Ethics, and the National Association for Female Executives.

  • April 17, 2015

    Danielle, so much wisdom, imparted in a way that enables / empowers us to take meaningful action. As I face a milestone birthday in August – and it ain’t 50! – I wish I had known so much more as a younger person to be a better person today. But it’s never too late to be late to the party, is it 😉

  • Nisha

    Leave reply
    May 15, 2015

    Thank you for this, Danielle! I’m getting started on my list of 25. Something else that I’ve been doing in my current job search, as I sit at home writing several variations of cover letters, is really questioning whether I’m presenting my authentic self, or getting caught up in selling myself. Am I REALLY excited about Organization X’s programs? Do my personal values REALLY align with Organization Y’s mission? If the answer is no, I’ve been trying to be intentional about foregoing those opportunities that don’t seem like quite the right fit…..very different than how I applied for every entry-level job under the sun when I was 22. Having options truly is a double-edged sword, but I’m hoping for a fulfilling outcome – this time via intentionality, rather than the blind, stumbling luck of my early-20-something self.

  • Connie McCoy

    Leave reply
    May 26, 2015

    Danielle, this recent post is very inspring to me as I am at a pivotal time of change in my career, wrapping up four years of teaching English abroad. I’ll be returning to the US in a few months and while I still want to teach I look forward to changing course to perhaps create my own position allowing for the anticipated slack job market in my field where my home is, and also to better apply my experience, evolving interests and convictions. Your four-step plan provides me with a great platform to hone in on and define my direction. Thanks!

  • July 3, 2015

    This is one of the best things I have read on the internet – have been casually researching aspects of this topic and it’s so refreshing to find a process of practical solutions. Thanks so much!

  • October 25, 2015

    Great post! THANKS!

  • November 3, 2015

    Very interesting and knowledgeable post. Thanks for sharing.

      • April 8, 2016

        Hey Danielle, Thanks for providing FREE e-workbook. And about your post, I’ll definitely go with Janette.

  • October 24, 2016

    Hi Folks
    I remember struggling with this identity crisis many years ago.
    I wanted to be successful pop musician, or an artist. My focus switched back and forth every two or three years, and neither seemed to offer a stable future. I finally had an opportunity to work as a graphic artist in a university print shop where I would have medical and dental benefits, union support, and a defined benefit pension. I kept doing music on the side, but I felt lucky to be making posters, brochures, typesetting books and newsletters while making good money and meeting interesting people from all over the world.
    This spring I retired. After spending 27 years working in a basement office I wanted first of all to spend all my time outside!
    It has taken about six months for it to sink in that I no longer have someone telling me what I should be doing every moment of every day, and that it is up to me to find something meaningful to do with my newfound freedom.
    I want to tell you that the choice you make now is not irreversible, that technology will perhaps change what is a viable career and what is not, and open up new possibilities. I want to tell you that in the future you will face many more moments where you will have to trust your instinct and decide which path to take. It’s not easy to be fearless and prudent at the same time.
    Just don’t let someone else tell you what you should do.
    There is a story that when you have a choice to make, you mentally toss a coin in the air, and while you wait for it to come down, you know whether you want it to be heads or tails. And in that instant you know what you should do.
    And that there will be more times when the chance to change course will present itself.

  • May 21, 2017

    Great article. Thanks for sharing this.

  • June 29, 2017

    I love the starting with 25 and dwindling down to 7 and not cheating by listing the first 7! On my list, the best ideas often come later. 🙂