Defining success

I had dinner with a friend recently and it became clear to me that we had two very different definitions of “successful.” It’s funny how one word can have so many different meanings, and its meaning can change tens or hundreds of time over the course of your life.

My friend is in her mid-20s. Her definition of successful, at least what I interpreted, is to have a high-powered, high-paying job for an elite company while also having a happy marriage and being present for her kids. She doesn’t have kids yet, which is what got us talking about things.

When I was in my early- to mid-20s, I maybe had some of those same visions, although I knew I didn’t want kids. Aside from that, I wanted to have an important job with an important company while balancing a happy and healthy relationship.

Forming my definition of success

How did I come to this definition of success? I’ve always enjoyed pleasing people, and I especially enjoy making my parents proud. I wanted to have a job and a life that was worthy of my parents bragging to their friends, extended family and coworkers.

When I was growing up, the way to succeed was to do well in school, go to college and do well there, then graduate and immediately get a job that will set me on a path for continual and gainful employment. So that’s how I gauged my early success: I got good grades in high school, I got good grades in college, then I made sure to secure a job upon graduation with a company people had heard of. I was the epitome of my definition of success. Once I started my first real job, I planned to continue on that trajectory and climb the corporate ladder.

What completely changed my outlook, however, was that as I progressed in my career, all the people I saw in these high-powered jobs seemed miserable. Let me try to restate that: I interpreted their lives as miserable. They were working 60+ hours a week every week and they were working while on vacations. They didn’t know any pop culture references because they didn’t have enough time to watch TV or listen to the radio or read a gossip magazine. The horror! Every email in their inbox was business critical.

It’s possible that they were happy living their lives this way. But to me, it looked and sounded like a miserable life.

I would try to remind myself that those high-powered jobs came with hefty salaries. When they were checking emails and making business calls on vacation, their vacation might be at a private villa in the Caribbean. When they had to work on weekends, they might have been doing it from their uber-amazing lake home.

The idea of private villas and lake homes sounds amazing to me, but I’m just too lazy for the work and dedication that goes into all of that. I think America defines success as having private villas and lake homes, but we don’t talk a lot about all the stuff that is sacrificed to achieve and maintain that “success.” No one pays attention to the opportunity costs: time with friends and family, time for yourself and time to exercise, de-stress and get eight hours of sleep most nights. We tell ourselves there will be plenty of time for that later.

There’s something about America where we feel like if we aren’t working 60+ hours a week, maybe we’re not true Americans and we’re not successful. We want to make sure everyone else knows how dedicated we are to work and to achieving success. This is crazy.

I’d like to tell everyone what their definitions of success should be, but I can’t. Everyone is wired differently – your idea of success might sound like another person’s hell. I also think it’s important to remember that no one loves every aspect of every job they ever have, and that when you’re young, you will be in a number of jobs that aren’t super fun. Your mission in your 20s and early 30s should be to learn as much as humanly possible and smile even when you don’t feel like it. The more you learn – even if it’s about tasks or skills that don’t seem interesting – will give you choices down the road. I promise you. Knowledge really is power.

My current definition

Success – for me – revolves around what makes me happy.

Most of what makes me happy isn’t material – it’s spending time with my loved ones and enjoying my hobbies. However, for me, it sometimes takes money to do really fun and memorable things with loved ones and to fully enjoy my hobbies. I want to be clear that I enjoy having money and spending it – I am not a minimalist, even though it’s something I admire.

I have to have a job with an income. I’ve had two jobs in my career that have made me miserable. I learned quickly that I’m not someone who can handle hating my job. While some people seem to be content with being miserable for long amounts of time, I couldn’t do that. When I had my first misery-inducing job, I quit without finding a job with a comparable salary and went back to the retail job I had in college. By the time my second misery-inducing job came around, I was in a position where I’d need to replace my income with something similar – I went into hardcore job-hunting mode and was able to find things that were much better fits after six or seven months.

I have a lot of friends who work in very stressful jobs. This makes no sense to me. Maybe other people are better skilled at weathering the storm. To me, it seems more like a waste of your time and, more importantly, your life. You only get one life, right? So why would you spend any of it being overly stressed and unhappy when you can make other choices to make it better? Maybe my friends didn’t feel like they had other options. Maybe they were making really great money and they told themselves that they just had to get through it for “X” number of years.

But wow: years?! You’re going to let yourself be miserable for YEARS because a job pays well?! I know I was just saying that life takes money, but come on, there are other jobs out there that will pay comparable salaries. Or, if there truly aren’t, look at your life and cut out some of the non-essentials in order to allow yourself to take a lower-paying position. Life’s too short to be miserable!

The power of money: freedom and shackles

Sometimes we make a lot of bad financial choices that make us feel forced to stay in a miserable job because it pays so well and will help us diminish all those mistakes we made in our past. This is a huge reason why I tried really hard to make good financial choices in college – I didn’t ever want to be stuck somewhere or in a situation because I was trying to pay off debt.

My family didn’t have a lot of money most of my childhood. Those years were really hard, but I learned so much. I told myself that I would do whatever I needed to do to never be in a bad position with money. Some bad things that happen are beyond our control. However, we can control our preparedness for them. In high school and college, I worked as often as I could in order to stockpile money so that whenever something bad and unplanned might happen, I’d be prepared. I wanted to make sure that I always had choices and that I was financially independent and stable. I didn’t want to be forced to stay in a job I hated, working ridiculous hours, just so I could afford to live.

I’m being a little harsh on my workaholic friends right now. I know there are people who LOVE their jobs and have jobs where it doesn’t feel like work, it just feels like exhilaration and fulfillment. I just don’t happen to know any of those people. Other than a couple entrepreneurs. But absolutely zero people working a corporate job.


Seriously, what makes you HAPPY? Does working 60-100 hours a week make you happy? Does it make you a better person? When you are on your deathbed, will you say, “Wow, I’m so glad I worked as many hours as I did”?

When I’m on my deathbed, I want to think about all the awesome trips I took with my mom. I want to think about the awesome life I’ve created with my boyfriend. I want to think about the awesome friends I have and the connections I have with those people. I want to think about the other awesome ways I’ve spent my time: taking my dog for walks in beautiful, peaceful places; writing a blog that inspires someone in some way; telling stories that inform and entertain people; and having an insatiable appetite for learning.

I will never think: “Wow, I wish I could have sent just a few more emails to Pam in accounting” or “wow, I wish I could have gone to a few more meetings about strategic planning.” I don’t want people at my funeral telling stories about how dedicated I was to a COMPANY – working nights, weekends and vacations. Why be dedicated to something that isn’t dedicated to you? When you move on, they will hire a replacement and their lives will go on. Yet you devoted SO. MUCH. TIME. And so much LIFE to them. What a miserable-sounding way to live. That doesn’t sound like success at all.

Throughout all of my life, my dad has instilled in both me and my brother this one question: “Why do people make life harder for themselves?”

For me, it rings true in so many ways. Stop making the choices that make you miserable – whether it’s work, friendships, relationships or how you spend your time. One bad choice typically leads to quite a few more down the road. Success is about how you make your choices. What kind of legacy are you CHOOSING to leave? Do you want it to be about how many lives you changed for the better or how many dollars you made for a company that will forget you shortly after you’ve left?


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