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The 3 Questions That Will Measure How Successful You Are

Find out how to measure success and what it means to you in our latest blog post.

By Robert L. Dickie III

Have you ever found yourself feeling fairly satisfied about where you are in your life—maybe even feeling rather successful in one way or another—then in the next moment, as you scroll through your Instagram feed, any good feeling is quickly squashed by your old college roommate smiling in front of his new construction, gigantic home? Gone is any sliver of pride or feeling of success, as pretty much anywhere you look (especially on social media) you see someone “better off,”—a higher paying job, a fancier vacation, or a bigger house.

As we all know, social media doesn’t tell the full story. I’ve met plenty of people who have the grand homes and hold fancy job titles— Vice President of this or CEO of that—and yet are actually quite miserable.

That investment banker who seems to be living the high life may be mired in debt, spending her nights drinking to forget her money woes. That family trip to Hawaii looks great in the pictures but was maybe filled with awkwardness as no one knows how to talk to each other or spend quality time together. That fancy new house is a constant money pit as there are so many elements requiring attention and upkeep. Having more often leads to an endless cycle of feeling like we still need more. You might be in awe of your old buddy who has yet another new impressive-sounding job, but that lifestyle may not be as glamorous as it sounds. We equate external achievements with success and are surprised when those don’t bring the fulfillment we expected. That’s because success is what you define it as, and everyone has their own metric.

A person might decide that, for him, success means having a close relationship with God, a healthy family environment, and a meaningful role in their community. But then he heads over to Facebook to see what his friends are doing and he feels inadequate because he doesn’t have vacation photos or impressive career updates to share. Suddenly, he becomes deeply unhappy because he’s measuring his success according to someone else’s metrics. One will never feel they have enough carrying on this way.

Every person has to define what success will look like in their own life and then measure using only this standard. We have to become self-aware enough to know that by some people’s standards, our lives won’t look successful since they define success in a different way. The second part is learning not to be bothered by others’ opinions of your success, or lack thereof.

Keeping to our own definitions of success is especially important when it comes to our careers. We’re all too familiar with the stories of Bill Gates, Oprah, and Steve Jobs who are painted as portraits of true success, and we internalize the idea that if our stories don’t look like theirs, we aren’t making a big difference.

You can build a meaningful career and have a wonderful success story no matter what your job is. Here are some questions to ask yourself to help you measure your “success” in your work. Note how these are not questions about your paycheck, vacation time, or number of promotions.

1. Are you giving it your all?

You cannot make an impact if you have one foot out the door. When you take on a new job, invest yourself mentally and emotionally. Trust me: your boss knows when your heart is not in your work. You might do enough to avoid getting fired, but you’re never the one staying late, volunteering for new projects, or offering ideas.

Live your day with purpose. Make it your mission to find meaning in the tasks you’re assigned each day. Not only will you find contentment within this attitude, you’ll also increase your value within the company. Find a company that inspires you, show up every day ready to give your all, and you will soon become an indispensable member of the team and probably start to really love what you do.

2. Are you constantly worried you’re missing out on something better?

Our culture has been infected by FOMO—“fear of missing out.” The desire to see and experience “all the things” leads people to move quickly from job to job, always drawn by the allure of the next big opportunity. But great careers are built with time. It takes years to hone your skills, understand your industry, try on different roles, and create sustained value. Jumping from one interest to the next keeps your contributions and skills at a surface level; real meaning and talent is cultivated through years of experience.

You could spend a summer traveling Europe or you can spend your summer exploring one country. The former sounds more fun, more exciting, and you won’t miss out on any must-sees. But if you choose the latter, you really get to know a new country in an intimate way. You’ll meet people. You’ll start to learn the language. You’ll be able to find your way around. You’ll see lots of places and things you wouldn’t see if you only stayed a few days.

The same holds true for career decisions. One person might hop from job to job, always seeking the more impressive title or the sexier company. Another might stay with the same organization for 10–15 years, slowly moving up the ranks and getting to know the business. The former has a more exciting track record on social media. But the latter has made a far greater impact in their industry.

If you're trying to determine how successful you are at your job, ask yourself what your core focus is? Are you multitasking too much?

3. Are you trying to do a little bit of everything?

When you’re young, it’s easy to be tempted by every shiny object: a new start-up, an investment, an attractive part-time gig, or an opportunity to wear a few different hats at your current workplace. But as you grow older, you’ll wish you had invested more in your specific/favorite area of work. You’ll regret trying to do everything that sounded interesting instead of drilling down into the one area that really inspired you. If you’re trying to do it all, you’ll get worn out fast and it can be difficult to realize where your passions lie. Committing to one thing and investing your heart and time in it will reap a lot of rewards.

The key to success is creating your own definition of what success is and then investing completely in your chosen work. If there’s a particular outcome you want to achieve, keep it at the forefront of your mind. Above all, don’t let yourself be distracted by other people’s version of success. What you see on the outside often tells you very little about how well things are really going. Focus on your own path and your own measurements of your success.

Follow Robert Dickie III on Twitter @RobertDickie and on Taking the Leap Podcast. You can tune in on Apple Podcasts, Spotify, or on your favorite podcast player.