man thinking
Shutterstock

How do I figure out if I’m on the right path?

It’s a question that’s often on the minds of many professionals, but can sometimes be hard to figure out the answer in the midst of the daily grind. Who has time to ponder this when there’s so much to be done right now.

Well, I recently attended the 99U conference about having a successful creative career and realized this very question proved to be the common thread that ran through many of the talks and conversations.

Luckily, the speakers at the conference offered some simple strategies for keeping yourself honest and carving out some time to reflect. Try one of the following exercises—or combine all three!—to confirm that you’re spending your time right, doing meaningful work, and on the career path that’s best for you.


Daily: Keep a Streak of Days that Matter

There’s no single “right path” but, at its simplest, being on the right path for you means spending as much of your time as possible doing work that’s fulfilling and meaningful.

How can you gut check that this is true? It’s as simple as asking.

Chris Guillebeau, author of Born for This: How to Find Work You Were Meant to Do, suggests that every day before you go to bed you should ask yourself: “Did today matter?” It’s a broad question that can mean many different things to different people, but that’s the point. It’s about the feeling in your gut, the feeling that your day was worthwhile in some way.

And while not every minute of every day can be filled with exciting work—all of us have to spend some of our time answering emails, filling out stat reports, running errands, or other mundane tasks that support the important stuff—the goal is that most of your time feels worthwhile.

To keep an eye on whether your balance of meaningful days is getting out whack, use a habit tracking app like Momentum or Streaks to check in every night. If your answer to “Did today matter?” is yes, say you completed the habit—if it’s no, say you didn’t. Over time, this will give you a quick visual representation of how many of your days (and weeks and months) have mattered. Obviously, you’re looking for a nice long streak of seeing that “today mattered.”



And if you start to notice you’re only having a smattering of “yes” days? Well, it might be time to think about exploring a new path. Or, at the very least, figuring out what’s causing you to say “no” so often.

Weekly: Look Forward to Your Funeral

I’m sure you’ve heard of this (slightly morbid) exercise before—you know, the one where you think about what you want people to say about you at your funeral in order to help guide your priorities—but bear with me. This activity from Treehouse CEO and co-founder Ryan Carson takes it one step further to make it super actionable.

Start by making a list of people who are important to you—the guests (if you will) who you’ll want attending your funeral one day. You can either list out specific people or list it by different roles in your life: your friends, your parents, your siblings, your colleagues, and on and on.

Then, under each person, list the things you want that person to say about you at your funeral. Carson’s examples were pretty high-level—he wants his wife to say he was loving and selfless, he wants his son to say he was strong and dedicated time to him—but I could also see this working for specific goals. Maybe you want your colleagues to be talking about all of the amazing novels you wrote, or that game-changing piece of software you created. Whatever it is you want to be remembered for, from the big to the small, write it down.


Now comes the part where you keep yourself accountable and make sure you’re spending your days right, dedicating your time to actually achieving these goals. Carson suggests spending 20 minutes every week looking over your list and determining places where you aren’t living up to your vision of yourself. Then, actually put time on your schedule over the next week or two to move closer to those things. Do you want your mom to say you stayed in touch with her? Schedule in some time to call your mom. Do you want your colleagues to remember you for doing creative work—but you never actually get to spend your 9-to-5 doing creative things? Block out a few hours to work on a project more in line with that vision, even if it has to be on the side after work.

Over time, these small incremental changes will help you become more of who you want to be—and get you closer to the right path for your life.

Yearly: Resign From Your Job

I’m going to start this section with a major disclaimer: We are not suggesting you actually resign from your job every year.

Instead, as Guillebeau explains in Born for This, “every year, commit to yourself that you’ll choose to break out of prison and do something different unless staying the course is truly the best way forward.

That means putting an annual appointment on your calendar to quit—and then every year at that time stepping back and evaluating your life and career. Is continuing on with your current gig another year the best coarse of action for you? Are you still learning, growing, excited, passionate about what you’re doing?



If the answer is a clear yes to you, then you can not quit and “proceed with confidence and give it [your] all.” If the answer is no, you may not want to walk out the door that day (in fact, you definitely don’t want to do that), but it is probably time to start looking for the next thing.

And, if you’re not sure whether you should leave your company or not, consider carefully what’s working for you, what’s not, and what you might be able to do to fix your current job instead of peacing out altogether.


No, none of the above activities will magically point to the “right path.” But by dedicating yourself to regularly evaluating your current situation and how that aligns with your feelings and your long term goals, you’ll slowly but surely nudge yourself onto the best path for you.