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Advice / Succeeding at Work / Getting Ahead

6 Questions to Ask Yourself to Know if You're Successful

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A couple of years ago, I quit my stable corporate job to become a freelance recruiter. I had tons of great reasons for making this move, but ultimately, I wanted more flexibility and less stress. After a few months, I’d scored some solid clients and was this close to not having to pull money out of savings to pay the bills. Overall, I was feeling pretty good.

One of the things I love most about this industry—whether as a freelancer or an in-house employee—is that I get to hang out on sites like LinkedIn all day long. The downside of that, at first, was being constantly bombarded with updates about my connections’ fancy new job titles or big promotions.

It seemed like all my friends were getting substantial raises, taking incredible trips to foreign countries on the company dime, or scoring major career wins. I was really happy for my friends, but I couldn’t help feeling a little left behind. I even started to question whether I’d made the right choice. Maybe I should’ve stayed the course and kept climbing that corporate ladder.

When I finally opened up to a fellow freelancer about my struggles, she reminded me that the very reason I’d gone out on my own was because I wanted to step away from all the stress, chaos, and pressure that’s intimately intertwined with those promotions and raises I was envying. I’d forgotten everything that went into the career milestones everyone around me was achieving.

The thing is, success is totally subjective. My version of it revolves around being able to go to a yoga class at 10 AM or working from a park bench on a sunny day. The flexibility that comes with this career path is so important to me that it’s worth the uncertain journey.

I know tons of accomplished people who absolutely love the work that they do and are happy to put in long hours at the office, travel for weeks on end, or wake up extra early to squeeze in a jog before an 8 AM call. Being able to juggle a robust schedule while doing fulfilling work is someone else’s version of success. It’s different for every one of us.

With all of this in mind, if you’re feeling a little down about where you are or asking what it means to be successful I have a few questions for you. And some advice, too.

1. Are You Happy?

Do you enjoy the work you do? Or at least most of it? Are you able to find time to hang out with your friends and family or pursue your other interests? If you’re happy, you’re already successful. Liking your job, appreciating your time off, and feeling an overall sense of contentment are huge wins.

If you aren’t happy in your job, don’t like your company, or can’t stand your boss, that’s OK, too. You just have to get a jump start on finding something new. Polish your resume, optimize your LinkedIn profile, and get your networking gameface on. You can–and will–find a better fit.

2. Can You Pay Your Bills?

Or at least put a decent meal on the table? This may seem like a low bar, but being a responsible adult who is not only able to pay their bills, but who can afford groceries every week is not nothing. Bonus points if you’re banking a few bucks in your savings account every month. Being able to afford shelter, food, and—hopefully—a little fun is the reason most of us have jobs in the first place. If you can check all three of those boxes, you’re in good shape.

It took me years to work my way out of student loan debt and a few lingering credit card bills, and I’m not ashamed to admit that I subsisted on pickles and crackers (don’t judge) on more than a few occasions. So, if you’re still working toward financial stability, know that you aren’t alone.

3. How Do You Define Success?

Ditch the idea of what you think success should look like, and ask yourself what it looks like for you. Do you want to make your own schedule? Help others? Be the go-to person on your team? There’s no wrong answer.

I can’t stress this point enough. There’s so much more to being successful than what an impressive job title or big paycheck indicates. That stuff is all great, but try digging deeper.

If you’re dying to land a director-level job, ask yourself why. Are you passionate about managing a team, excited about taking on new challenges, or hoping to land a seat at the decision-makers’ table? If you define success by your salary, ask yourself why you want to make that much. Are you hoping to retire early? Travel the world? Support your family? Whatever your answer is, remember that the definition of success goes far beyond an important title or a six-figure paycheck.

Personally, I’d love to be a rich, world-renowned expert in my field. And maybe I will be one day, but for now, I’m setting my own hours and making enough to support myself, while earning the trust and respect of my clients.

4. What Can You Do Now That You Couldn’t Have Done a Year Ago? Five Years Ago?

In other words, what have you learned? Think about all the things you didn’t have any experience with or weren’t very efficient at when you first started your current job. I bet you’ve accumulated a wealth of knowledge and skills since then.

When I first started out in HR, my new boss taught me how to use a super complicated spreadsheet to track company healthcare expenditures. It took me forever to update everything, but I eventually got the hang of it. By the time I left that job, I had to reteach my manager how to use the spreadsheet!

This may sound a bit trivial, but it’s still a victory. Dedicating time and energy to getting really good at your job is something to be proud of–regardless of how big or small the task. I’ve no doubt that you have stories like this. Write them down. Be proud of them.

If you feel like you aren’t learning or growing anymore, there are lots of ways to challenge yourself. Are there any professional certifications you’ve been thinking about pursuing? Are you interested in taking on new responsibilities at your current company? Is it time for a complete career pivot? Spend some time thinking about what you want to learn next, then go after it.

5. What Are You Most Proud of?

Write down everything you’ve accomplished throughout your educational and professional career. And include your personal life, too, while you’re at it. This could be anything–the semester you earned a 4.0 GPA, that time you pulled off a last-minute presentation, or the day you finally stuck a solid handstand in yoga class.

Taking inventory of your accomplishments from a holistic viewpoint can help to put your actual level of success in perspective. We tend to focus on our failures, so keep your list of wins as a reminder of how much you’ve achieved.

Look back on your triumphs when you’re feeling down and focus on how far you’ve come instead of worrying about the things you’ve yet to achieve.

6. Are You Working Toward Something?

What are your career goals? What do you want your life to look like? What type of person do you want to be? Now ask yourself if your current job or career path is going to help you get where you want to go. If the answer is yes, you’re more successful than you think.

If you feel like you’ve gotten off track, that’s totally fine (and normal–I’ve made a few career missteps myself). Recognizing that it’s time to make a change is the first step. Defining your goals comes next. Then you’ll need to make a plan. And just like that, you’re working toward something again.

Questioning your career path or feeling insecure about your success is totally normal, but comparing your progress or achievements to someone else’s isn’t going to do you any good. When in doubt, remind yourself of what your version of success looks like and keep working toward it. You’ll get there eventually–and I know you’ll have a lot of wins along the way.

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