Identify your what if
“Find your passion and live it every day.”
Jacqueline Segall Caplan
When you look at the world’s most successful and inspiring people, they all seem to have one thing in common: they are passionate about what they do for a living.
But is that true?
Did they get there because they were passionate to start, or are they passionate now because their destination became a success? I venture to say there is a combination of both. I can say one thing with certainty: No one stays the course through the challenges of life unless they are laser-focused on something for which they care deeply.
It is easy to yell out answers to the question, “What do you want to be when you grow up.” When I was a kid, all of my friends and I had the standard responses: pilot, doctor, president, and astronaut, but none of us knew what those careers entailed. In most cases, those professions had nothing to do with the things for which we had any passion. They were just seemingly cool things to do.
Once upon a time, I wanted to be a doctor. My parents worked in medical institutions, and so I knew many doctors and respected them very much. I thought it would be amazing to do what they do and to command the respect they had from people like me and most everyone else.
But was I truly passionate about medicine? Passionate about biology and chemistry? Was I four-years of medical school and another 3-7 years of a residency program passionate about being a doctor?
No. Not even close.
I was, and still am, passionate about helping others. I couldn’t imagine how that passion could turn into a career, but of course, there are many jobs out there that help people. I even view what I do now in software development less about selling widgets and much more about helping people overcome a difficult task and accomplish an important goal.
Being able to frame the work I do in a light that is more about helping people is very important to me. That is what drives me every day. Some days are more about making the world a better place than others, but over the long arch of my life, it is this fundamental driver that pushes me forward.
A case study in flexibility
When I was 18 years old, and about to begin college, I had recently returned from a year abroad in Germany and a six-month solo backpacking trip across Brazil. These were very formative experiences in helping me understand what I most valued in life.
It was at this time that I wrote the mission statement for my life. It reads, “to make a positive impact on people’s lives while working in the international arena.” I did not know what that meant at the time, and in many ways, I am still figuring it out, but this is the core value by which I measure all of my decisions as being a good fit for me or not.
I had my mission statement in hand and was beginning university. But what to study? I found the answer in Political Science with a concentration in Foreign Policy.
My education in politics was fascinating. I loved what I was learning, and I was very engaged with the political crowd. I climbed the ladder of Student Government, from college senator to student body Vice-President. I memorized Robert’s Rules of Order with the enthusiasm that my friends learned the latest Beyoncé lyrics.1
You see, I planned to study foreign policy, give two years of service in the Peace Corps, and then take, and hopefully pass, the U.S. Department Of State’s Foreign Service Officer Test to become an American diplomat. The diplomatic corps was where I thought I could best accomplish my life’s mission statement.
And then, in my senior year, it happened: disaster struck.
I was in the middle of a class called “Foreign Policy,” when I realized: I don’t like this. Everything came crashing down around me. My Golden Brick Road disintegrated right in front of me, and I no longer had sight of my path.
Suddenly I realized that I wanted no part in fighting for resources at the expense of others’ ability to live happy lives. At that time, diplomacy seemed to be more about how to make America a winner at the expense of others. Those motivations didn’t align with my values at all.
I further realized there were exactly three things I could do with a Political Science degree:
- Go to law school,
- Intern for some political office, or
- Have a career change.
Choosing a career change was a no-brainer.
But to what could I possibly change? I had just invested my entire collegiate education into the pursuit of a career in federal service. The only career direction I had ever had disappeared just a few weeks before graduation.
So now what?
Well, this was easier than I thought it would be. Easy because I allowed the answer to come organically. I let my heart lead the way, and all of a sudden, it became clear what my next step should be.
In Student Government, I honestly was not all that interested in the organization’s policy discourse. You see, while all of my political comrades were busy debating political philosophies and partisan politics, my focus was overseeing a nearly $200,000 annual budget to plan the big spring concert, a battle of the bands, and a few other programs related to student wellbeing.
I also had a student job working with my university’s athletics department as part of their event management team. As part of the events crew, I put together sporting events attended by thousands of people every week.
It was exciting, and I loved every second of it.
During my last two years of university, I spent all of my available mental energy organizing these large-scale events. I am also a drummer and had a touring band in college. I’d even spent a summer in Las Vegas playing music at many of the casino lounges on The Strip.
My passion was not in foreign policy. My passion was event management. Specifically, I loved the logistics that went into making music festivals.
I was going to graduate in just a few weeks, and how could I even begin to think about such a drastic change in career direction at this time with finals just around the corner? Luckily for me, my passion was evident to the professionals whom I had hired to produce these concerts on campus. They knew I was about to graduate, and sitting on a tour bus backstage at a Chevelle concert, a legend of the concert promoter industry asked if I would like to be his right-hand man at Green Machine Concerts. My Plan just took a dramatic turn, and I was flexible enough to say yes!
My time as a concert promoter does indeed make for a fascinating story. I can tell you about encounters with the likes of Taylor Swift, ZZ Top, The White Stripes, Wyclef Jean, and many others, but we would come too far away from the point of this story.
The point is this: an essential element to any plan is the flexibility to change. Allow yourself to be as flexible as you grow. By doing this, you will always be able to achieve what is most important to you.
Let us shift the focus back over to you now.
We are going to do two exercises which will help you formulate a plan for your life. The first is called the “Life Goals Exercise,” and the second is the “20-Year Plan.” Follow along by using a sheet of paper or your favorite notes app.
Life Goals Exercise
As you are the type of person who would read a book like this one, you might already have some life goals identified, and a plan thoroughly thought out. If so, good for you! But, I still encourage you to give this exercise a try.
You should review your goals and plans regularly; after all, your aspirations from a year ago may have changed until today, and they might change yet again a year from now. Therefore, plans need to be updated as your goals change.
What we are going to do now is very simple, but you should still take some time to think about it. After you do this exercise, you should come back to it later today or this week, and read through what you wrote down and decide again if it is reflective of who you are and what you want or not.
Your main goal
The Life Goals Exercise is intended to help you identify your core passion and some tangible steps you can take to live a life which advances you toward fulfilling that passion. So let us start by you filling in the blank in this sentence:
Keep this thought very broad; very high-level. Don’t get too specific with it right now. For example, when I first did this, I wrote down “to make an impact.” Maybe you want to be a doctor, then you could write “to save lives,” or you want to join the military so you can write “to serve a mission bigger than myself,” so on and so forth. Think of this as the driving force behind WHY you want to do whatever it is you would like to do with your life.
Again, there is no right or wrong answer here, and you are most welcome (and encouraged!) to revise this later. We, humans, are, after all, evolving creatures with ever-changing needs and desires. However, I believe if you get this line correct, it should not need much changing, because this should reflect your inner core and what drives you to do all the things you do in your life.
Contributing objectives
Write a numbered list, 1-15. With this list, you will identify some contributing objectives to the life goal you have written. A contributing objective is an actionable step you can take that is more short term or quantifiable than the life goal. These are the things you might like to accomplish throughout your life, the completion of which will signify that you are fulfilling your life goal.
You do not need to fill in all 15 contributing objectives, but you may also feel free to do more than 15. 15 is a pretty good target which gives you plenty to work with, lots of flexibility later on in life, while also keeping the list concise enough so that you do not get lost in an endless list of potential activities.
I’ve filled in the first three contributing objectives here from my own Life Goals Exercise2 so that you have a few examples of what scope of activities you could have on your list.
All of these are specific enough to provide me with direction, but also vague enough to leave me plenty of flexibility for how I achieve each item.
You should feel very free to come back to this later. This list can and should be a living document, something that, as time passes and you grow, you will want to revisit and edit.
Prioritization
Before moving on, can you rearrange this list in such a way that it becomes priority-ranked? Move items that are most important to you to the top, and the less-important items toward the bottom.
Once you have this list of priority-ranked contributing objectives written down, there is one more step before we can put it to rest.
Timeframe
To the right of each item, assign a time value, in years, for when you would like to have accomplished that item. Some of these will be ongoing and not necessarily have a completion date. That is ok. You can leave those without a time value if you genuinely feel that they will be consistent themes throughout your life.
Review
Great! Now you have identified the
- Overall experiential goal of your life,
- Contributing objectives to achieving that goal, and
- Specified a timeframe in which you hope to accomplish those goals.
Excellent progress! You should now feel free to reward yourself with a treat. For example, you could have a cupcake, a walk in the park, or, you can keep on reading! There is more work to be done here, so if you do take a break, come back soon while the last exercise is still fresh in your mind.
The 20-Year Plan
Now it is time to write a 20-Year Plan! Twenty years is a very long time, roughly 1/4 of the average lifetime of an adult living in the Western Hemisphere. But don’t fret, you have already done the hardest part.
Take a look at your list of contributing objectives. You can use these as the foundation for your 20-Year Plan because you have already assigned a time value to each item. Rewrite that list now according to those time values. Start the new list with the objectives you believe you can accomplish more quickly, and end the list with the things which will take longer to achieve, followed by the ongoing items with no set time value at the end of the list.
Try to write the items without a specific timeframe at the end of the list in some sequential order, if you see a clear way to do so. Perhaps by what is most important to you, or in dependency order.
This reordered list is now the foundation for your 20-Year Plan.
Maybe the timespan here is only a few years, or perhaps it is more than 20-Years; either way, that is ok. The idea is not to have a rigid list of things you must do. The point of this exercise is to give yourself a vision of the incremental things you can do that will lead to you succeeding in achieving your life goal.
The philosophy you should keep in mind here is that any plan, even a bad plan, is better than no plan. Additionally, the most crucial aspect of any plan is flexibility to change.
Let’s review what you have here. You have a life goal. You have a list of contributing objectives you would like to accomplish over a defined period. These items are reasonably broad, but they offer structure, and they contribute to the strategy of a longer-term goal.
So let us go one level deeper.
For each of these contributing objectives, write two concrete, specific Action Items that you can do to accomplish that particular Contributing Objective. These Action Items should be items with a precise definition. Examples could include:
- Complete a specific course or certification,
- Learn a new language,
- Submit ten photos to a contest, etc.
Here are a few items from my 20-Year Plan once I ranked them in chronological order:
Whew! You did it! You now have a 20-Year Plan! And if not for 20 years, then hey, that is also totally fine. You have a plan that gets you significantly closer to achieving your life goal, and that sets you far ahead of most people!
Now, remember, this is a living document. Make a fresh, legible copy and put it somewhere safe. Or do what I did and put it on your blog for the world to see. Or keep it secure in a Google Doc or on another cloud storage service. Whatever you do, just put this somewhere safe and where you can find it again in the future. If you want to be hyper-organized about it, you can even create some calendar reminders for yourself once a year to look at the document.
BONUS: 20-Year Plan Summary
You may or may not see some categories clumping together in your 20-Year Plan’s timeline. For me, I was able to think of all the details in my Plan in just three steps which clumped everything together nicely:
Can you write a summary of your 20-Year Plan? Think first about the most significant near-range item, then envision how you think the first ten years will look, and then how the second ten years might look.
You can see the entire Life Goals Exercise and 20-Year Plan that I did when I was 18 years old, and the progress that I have made thus far, on my blog at judsonlmoore.com/life-goals-exercise.
You can also subscribe to my newsletter there and receive additional tips and encouragement about goal-setting.
Being spontaneous
There is a lot more advice I am going to offer you about what to do with your 20-Year Plan, but before we dive deeper, let’s take a break from planning and discuss spontaneity.
Earlier in this chapter, I shared a philosophy about plans that I believe is truly valuable, “The most important aspect to any plan is flexibility to change.” This philosophy is critical. A long-term plan will not serve you well if you do not allow yourself the flexibility to make changes as you go.
People receive new information, opportunities, knowledge, and inspirations every day. As such, our desires and values will also change over time.
Planning is just goal setting. Goals also change. When a primary life goal changes, then you need to rethink the steps in achieving that goal, but you still need to take some time to contemplate what the best steps are.
Sometimes, the best step to take is a spontaneous one. Living in the moment and just doing what feels right without overthinking the benefits or consequences can often lead to the most rewarding experiences and memories. If a spontaneous decision is going to lead to disaster, you will probably have an idea about that possibility before jumping in, so hopefully, you will also intuitively make the best spontaneous decision.
I am going to discuss decision-making skills in further detail later in Chapter 4. The principles I will share with you there are going to help you make on-the-fly decisions as well as more long-term decisions. You will get a lot out of those principles once we get there, but for now, let’s get back to the planning phase and what to do once you have your life goals identified.
Finding inspiration all around
Inspiration exists all around us. The list of what inspires is infinite. Our family, our friends, our teachers, celebrities, nature, architecture, the skies above, books, and so much more all inspire us.
As with most things, not all inspiration is treated equally. We take much of our daily inspiration for granted, and may not even realize at the moment that inspiration is seeping in. We tend to think of inspiration as being necessarily grandiose and life-altering, and though this can also be the case, I believe that inspiration also comes from the small, everyday parts of life. I believe that these sources of inspiration have much more tangible impacts on the way we live our lives than any other source. Since this type of inspiration has a way to sneak into our lives, it is sometimes difficult to fully appreciate or even to identify when it is happening.
With your Life Goals and 20-Year Plan in-hand, let’s search together for some inspiration.
For each item on your Life Goals and 20-Year Plan, can you add some annotations with names of people or organizations who have inspired your desire for those actions in your life? Are these people that you know personally? If not, can you get an introduction? Can you engage them via social media or by writing them a thoughtful handwritten letter? There is no better feeling in this world than being told by an aspiring person that you are a source of inspiration for them.
If you can let it be known to these people that you look up to them, let them know the specific impact they have made in you. When you do this, mention what the specific actions are that you plan to take because of that inspiration. Let them know that you are not just passively sitting around awestruck and inspired. You must be inspired to action, that is what makes this inspiration special.
Once the inspirational person knows the action you are planning to take based on their inspiration in you, they will more often than not feel a vested interest in helping you become successful. Their interest can be a precious advantage few people will ever obtain because others seldom reach out.
Engaging mentors
A lesson I learned while serving in the U.S. Peace Corps is that if you are doing something for someone else, you should not want it more than they do. Sure, you should desire the fruits of your labor. You can even want it a lot. But if the person or organization whom it most benefits wants it less than you do, then you need to reevaluate your position on the task at hand.
Don’t confuse “want” for “ability to perform.” Lots of times, especially when volunteering, we do things for others who cannot do that thing themselves, which is likely why we are there in the first place. However, if that person desires this task to be completed less than you do, then you need to think about how much of yourself you should be putting into this. After all, you are there for their benefit, not yours.
Maybe it is your involvement that is too high, or perhaps it is the beneficiary’s enthusiasm that needs some attention. Is the effort you’re making a worthwhile effort? Will the results be sustainable? If you want the task completed more than its beneficiary, then the answer to these questions should be a resounding “no.”
The same is true for those who might be helping you. If you can get some influencers to mentor you, they will quickly go away if they feel the engagement is coming more from their side than from yours. So don’t pursue these relationships without some plan in mind. Luckily, you already have a great plan written down! Share your Life Goals and 20-Year Plan, in their entirety, with those who inspire you. They will be impressed with your organizational skills and that you have a personal vision written down.
Often, these mentors can help you along your path in many more ways than you (or they) realize at the onset.
Follow through
When you receive suggestions or to-do items from a mentor, be sure that you do them. Otherwise, say you won’t upfront. If you won’t, then also clarify why you won’t complete these items. Is it lack of understanding? Lack of ability? Lack of time? Hopefully, not a lack of interest, but if so, then you can probably acknowledge to yourself that you’re in the wrong place at the wrong time.
I am confident that 99% of the time that you actively reach out for advice, and receive said advice, you will take action on it. Right? Well, it happens less often than you’d think. Follow-through is very important. If you’re going to get some of a person’s most valuable resource, their time and their mind, be sure you do your part to follow through
Follow up
Imagine it has been a few days or weeks since you met with your new mentor, and you have either completed or at least started the actions they encouraged you to try. Let them know how it is going. This is so important for developing the relationship.
You don’t need every detail completed. Under many circumstances, it might be ok that you’ve not even started taking action on the steps yet. But you should still follow up and give a status report.
Do you have obstacles with the tasks? Let them know. Get more advice. That is the whole point of the mentorship, after all.
Mentorship
Your mentors are qualified as such because of their expertise and experience. Do not allow yourself to get caught up in all of their accomplishments. They have been working at it for longer than you have, and what you see are just the accolades and results. Few things come easy in life, and the rewards most worth celebrating often occur after long hard work.
Learn about your mentors’ path, how they overcame obstacles, and how they got their start. It is in this way that you can best learn from their mistakes and build your successful path to living your what if.
LIVE the if; don’t just dream about it
Now comes the critical part. Once you have identified your what if and have a few key sources of inspiration and support, you now have to go out and live it! Doing this can feel overwhelming at times, but those tangible Action Items which you wrote down as ways to accomplish each of the contributing objectives in your 20-Year Plan will serve as a great directional tool.
Are you working toward any of those action items already? What is holding you back? How can you measure when the action item is complete or is ready to advance to the next level? I believe that most of the time, these questions will be answered either with time or by merely contemplating them for a little while.
You are a smart person, you’ve come this far, you will know when things are working out or not. So get out of your way and let yourself be you.
There is a question I get asked more frequently than any other. All of my friends have asked me this. After spending a year in Germany at age 17, half a year in Brazil at age 18, playing music on the Vegas Strip over a summer break, quitting my job and moving to London on nothing more than a prayer, this one question always came back to me. I was asked many times, “Judson, how do you get to do all this?”
I never really understood this question. I certainly never gave a satisfying answer to this question. In response to the travel experiences, I would unsatisfactorily respond, “I bought a plane ticket, and I went!” I didn’t understand what the big deal was. I couldn’t perceive how others did not see these opportunities as clearly as I did.
The fact is, the real question they were asking me was, “Judson, how do you live your what if?” Many of those who asked were not living their own what if for one reason or another. Sometimes the reasons were more legitimate than others. My failure to provide proper context and encouragement to my friends and peers to go out into the world, take risks, and to live their what if, is the reason I started the #whileyoung 3 section on my blog and decided to write this book.
Solo backpacking across Brazil for six months when I was right out of high school did not happen “just ‘cause.” There was a thought process and a plan there. There were numerous rounds of evaluations and a cost-benefit analysis for the decision to go. I had to weigh the decision on which place would be my destination. The competing country was Australia, and it was hard to decide between the two locations. In the end, learning about the funnel-web spider in Australia helped me decide I would go to Brazil. Of course, that is silly, since Brazil has some of the biggest spiders in the world. But at the time, it was all the information available to me, so no regrets there.
This trip to Brazil became for me because I purposefully worked and saved money for it. I sacrificed my high school senior year after-school activities so that I could work at a Sears retail outlet and sell car stereos to my peers. I dropped my extracurricular classes (band and music in particular) so that I could accelerate graduation by six months. I missed prom and my graduation ceremony so that I could be in Brazil on a grand adventure.
To me, this was the most logical decision possible. To my peers and school guidance counselors, they thought I was making a mistake and missing the “most important experience of my life” by not walking across the stage to get my diploma. I thought they were crazy for advising me not to go to Brazil. I don’t think we ever came to share the same opinion on this one.
Even producing the final destination contenders of Australia and Brazil was informed by my previous experience as a Rotary Youth Exchange Student in Germany, where I met many other students from around the world, notably from those two countries.
As you can see, this did not “just happen.” I did not “just buy a plane ticket and go.” I had a plan. I weighed my choices. I lived my what if.
I cheated my friends for years because I did not do a sufficient job of explaining how I came to these decisions and led such an adventurous lifestyle. I hope they will forgive me and that I can win back some positive karma for sharing my story now, with you. My greatest desire is that you will go out and live your dreams after reading this book.
Stagnation
“Go mode” is not the default. There are times when we will stall out. The Plan will take a backseat to the realities of our life. We all have obligations with friends, family, work, and community that can slow down and even alter the course of our own lives. That is ok, that is life, and you can also celebrate the slow times as well.
But we can’t just sit around the campfire and sing Kumbaya forever. If we did that, eventually, the fire would run cold, and someone would have to chop more firewood. Those action steps you wrote down are like the wood for your Life Plan’s fire. You always have to be gathering more wood, or the fire runs out.
When you find yourself stagnating, or feeling like you’re not getting anywhere in your life’s ambitions, it is time to make some assessments. Try to identify the reason or reasons why you are not making progress.
Are you becoming disenchanted with your topic of study? Maybe what you have learned is that you don’t want to be the thing you are studying for when you grow up.
Is your job no longer challenging you and providing you with opportunities to grow?
Do you lack support or inspiration in some part of your life or even the community where you live?
Are your friends, or maybe a roommate, black holes who suck all the energy and inspiration out of you? It can be harsh to think about, but maybe your social group is holding you back.
If you can identify the place or places in your life that are not helping you rise to the occasion, then it is time to make some changes. Change, especially worthwhile change, can be challenging to make in the beginning.
If you are in your final year of university and realize that you need a drastic change in your studies that will delay graduation, that is a tough decision to make. But isn’t it better to make it now than to graduate with a degree which only opens doors which will make you unhappy?
Similarly, how long do you want to be in the comfort of the steady job that is going to get you nowhere?
Changing your social group may feel impossible, but there are always ways in which you can alter your daily routines, extracurricular activities, or surroundings so that you become exposed to new people and ideas.
Change often appears to be a sudden thing to outside people, but to you, this is a process which can, and sometimes should take quite a while to implement. After identifying that a change needs to come, you can spend a significant time seeking out the adjustments that make the most sense. It is good to investigate options, but don’t let the abundance or lack of apparent possibilities hold you back from making a change once you know you need one.
If you find that the change you made was not the best, that is fine, because then you get to make another change and will be all that much more well-prepared to choose wisely. This iterative learning process is a natural part of life and will come back into play later when we go into a more in-depth discussion regarding decision-making.
Multiple “ifs” balance
So far, we have been having a singular discussion about one primary life goal and the steps to accomplish that goal. However, it is more often than not the case that we have a variety of life goals.
So now what?
You might be thinking that accomplishing just one life goal sounds complicated enough, so how do you succeed with two, ten, even one hundred life goals? Well, I advise you only to apply the same steps we have already discussed toward each one of those.
Some of the goals may complement one another, while others may be so vastly diverse that you need an entirely different set of action steps to make progress toward those other goals.
Prioritization will help with sorting this out. Which goals are most important? Which goals require more immediate attention and effort? Which goals are time-sensitive and either require that you act today, or perhaps you must wait until a later stage in life before you can adequately address them?
As I mentioned in Chapter 1, I first had a goal to write this book about seven years ago. I wrote the working title, a simple outline, and had a general premise, then I shelved the project until three years ago, wrote the full outline and drafted the first three chapters, and stalled out again. I’ve had the writing of this book as a goal for a long time, but I also understood that I was not yet ready to write what I wanted to say. I required that a few more life experiences happen in my own life so that I could learn, grow, reflect, and eventually share a higher quality of learnings with my readers.
The only thing that makes me happier than to have succeeded in my goal of writing this book is that you are reading it! A tremendous thank you for being part of my journey.