The Mistake I made in Trying to Find Career Fulfillment — and What to do Instead.

Kelley Shields
4 min readMay 4, 2021

A lesson I wish everyone knew.

Photo by JESHOOTS.COM on Unsplash

I spent over a decade as an unhappy attorney trying to figure out what kind of work could actually be fulfilling and enjoyable for me.

Yep. More than a decade.

I took assessments, read books, talked to therapists, brainstormed, and read all the “50 Things You can do with a Law Degree” articles.

I even thought I had it figured out at one point and got my realtor’s license — something that seemed to make so much sense that my best friend said that she thought it would be the perfect job for me.

But again, not the right fit.

What Was I Doing Wrong?

I was making a mistake that I see almost everyone make when they are trying to figure out what they need in order to find career fulfillment — I was trying to answer the really big question of “What’s the right job for me?”

Reasonable, right? After all, that’s what I needed to know.

Here’s a secret: that’s too big a question.

What Should You Do Instead?

The key is surprisingly simple — yet it can be hard to find. It’s to take structured baby steps.

I am someone who wants the answers NOW. I want to figure it all out inside my head and then just go do the thing.

But, that doesn’t really work most of the time.

For example, going to law school was a decision that seemed to make perfect sense. Later, when I got a realtor’s license, that also seemed to make perfect sense. But I wound up figuring out after after investing time, effort and money into these big steps that they weren’t getting me to a place that I actually wanted to be.

I spent years stuck in jobs that weren’t right for me because I didn’t have the answer to the question “What do I want to do instead?” But, when I personally turned to coaching and started breaking down the big question of “What do I really want to do?” into a series of small, but strategically structured steps, I continually got more and more clarity until I was confident I was moving towards something that was actually right for me this time.

And it literally changed my life.

What Happens When You Don’t Do This?

I’ve done both of these things:

1. Freeze

I see so many people “freeze” and not take any action to change their situation because it feels sooooo overwhelming to try to figure out the whole answer from where they’re starting.

I talk to people who are wondering things like “Is it even possible to find work that I’ll like? And that will support me?” And I get it. Those are very real fears. And they aren’t bad questions to be thinking about. But they are BIG questions.

I see people get stuck in a kind of loop: because they don’t know what the answer is, they’re afraid there isn’t an answer, so they don’t take steps to figure out the answer.

It becomes a self-fulfilling prophecy, keeping them stuck.

2. Leap of Faith

And I’ve also seen the opposite happen. I’ve seen people feel like they should be able to figure out the answers on their own. They try to figure out those big questions all alone in their heads, and then take these big steps that they think make sense, like I did. They jump into a new field . . . but often then realize that it isn’t what they thought. And find themselves, after this big effort, again struggling to find career fulfillment.

I SO get it. Like I said, I want to know all the answers up front too.

But that isn’t where you want to end up either.

So What Should You Do?

Slow down. Recognize that there are a lot of smaller questions you need to ask yourself to figure out what it is that you need to find career fulfillment. You need to get clear on your individual motivators, needs and values, and to holistically look at the factors that contribute to career fulfillment. Focus on those smaller questions and use the answers to those questions as building blocks to answer your bigger question.

Here are some questions you can try asking yourself:

  • What are your natural strengths and gifts? What are the things that you are both good at AND also enjoy doing and find energizing?
  • What’s really important to you for your life outside of work? Do you need a set schedule? Flexibility? Time to do something major, like train for a triathalon or extensively travel? Want to be able to pick up your kids from school?
  • Are you someone whose work needs to have a mission or driving purpose?
  • What qualities describe a boss that you would work well with?
  • How do you like to work with others? Do you like to talk through ideas and collaborate with them? Do you need space to go off and do your own piece of a project and then bring your completed work back to the group?
  • What motivates you?
  • When in your life have you felt like you were making a meaningful contribution?
  • What accomplishments or experiences are you the most proud of?
  • What are you doing when you lose track of time?

The Takeaway

Sometimes you have to move slow to move fast. I know you want all of the answers yesterday and want to be making it happen today. But giving yourself the space — and the structure — to figure it out step by step is the fastest way to get to where you really want to be going.

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Kelley Shields is a career change coach, helping unfulfilled professionals find work they find meaningful, enjoyable and profitable. Feeling stuck? Don’t know what you want, but know your current job isn’t it? We should talk. Find me at www.kelleyshields.com

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Kelley Shields

Former attorney living my best life by coaching others to meaningful, enjoyable careers. www.kelleyshields.com