The Golden Rule of Career Change and Advancement

The Golden Rule of Career Change and Advancement


There are a bunch of ways we sabotage ourselves when trying to make the next career move.

To name a few:

  • Not being clear about what we want

  • Focusing on jobs we could do as opposed to those we want to do

  • Devaluing our unique strengths, experiences, and skills

  • Allowing fear, perfectionism, and limiting beliefs to cloud our vision

  • Sacrificing what’s most important


I could go on…

Yet I was personally struck the other day by the power of one particularly gilded Golden Rule: You’ll never know until you try.


Why “You'll Never Know Until You Try” Is the Golden Rule of Your Career

I’ve seen it hundreds of times, maybe thousands. You have a big dream, a lofty goal, maybe even the makings of plan…locked away in your head. 

Or maybe your dream actually exists on paper…a draft of that book you’ve always wanted to write, a business plan you’ve been working on for years, or the piles of research you’ve done on opening your own business.

But what steps have you actually taken to test it out and make it a reality?

Until you take steps to prove out your assumptions with real-world data, you’re letting that voice in your head talk you out of career moves that might be a great fit for you. 

And I’m not talking about the inner voice that says, “Great job, Self. You have so much to offer. All you need is the right role and organization to match. You’re totally killing it.”

I’m talking about the inner voice that says, “Hey there, Self. Sorry to remind you, but you’re not _______ enough. No one is going to take you seriously. You don’t have the _______ you need to make this happen. Remember that job you hate? It’s not so bad. You’re making money; can’t risk losing that. At least you can work from home once a week. Might not get that if you go elsewhere. You really should be more grateful. Do you realize how lucky you are to have a job at all?”

That voice is a loud-mouthed jerk, operating out of fear and regret 90% of the time, reminding you of the worst stuff that has ever happened, spinning specious tales about what could happen in the future, and presenting them both as truth. 

That voice is like a dude at the bar who speaks nonsense with such conviction that you find yourself questioning your own grasp of the facts (“All swans in England belong to the Queen? A duck’s quack doesn’t echo? How can that be? I gotta read up on this when I get home.”) 

The problem when we apply this metaphor to your career? You don’t go home and do the research. You listen to that Crazy Dude At the Bar voice without fact-checking him.

You don't actually try.


To Advance In Your Career, Stick To the Facts

The way to check the facts is NOT:

  • Spending five minutes googling until you're sucked into a YouTube vortex.

  • Making a Pro/Con list as to whether you should stay at your job or leave.

  • Having a running internal monologue.

  • Distracting yourself from your career by filling the void with exotic trips, shopping, or binge-watching television.

  • Any other delay tactic you trick yourself into in the name of “research.”


Checking facts IS:

  • Being honest with yourself about what you want and committing to look for it.

  • Getting out there and talking to people, whether they're in the job you think you might like, or in a position to hire you or create something tailor-made.

  • Building relationships with people you want to work with and for.

  • Getting your foot in the door by any means necessary (And no, that doesn’t mean working for free. Seriously, stop talking yourself into that.)

  • Taking steps to start your own thing.

  • Putting your creative gifts on view for the world to appreciate.

  • Doing the work of a role you aspire to and lead as if you’re already in it.


No. More. Hiding.

You must see and be seen.

Until you try these things, and gather real-world information, you cannot know whether your next career move is the “right” one. You have nothing to base it on but your Crazy Dude At the Bar voice. 

And just imagine how much more educated you'll be once you spend a bit of time each week actually doing so.

Here’s the beauty: If you try something and don’t like it, you don’t have to do it anymore. There are so many low-risk, low-commitment ways to find out more without going all in or turning your career upside-down.

You can do all these things on the side as long as you want to continue finding out more.


The Not-So-Winning Formula For Career Happiness and Fulfillment

There’s a well-known and not-so-winning formula to ensure you’re not successful. 

It goes like this:

  1. Have a great idea

  2. Spend hours, days, or weeks super excited about it

  3. Stumble upon an element that scares, intimidates, or stresses you out

  4. Lose all excitement

  5. Abandon idea fully

  6. Repeat

My Career Disillusionment Theme Park would also feature this terrifying birthday-party-clown-slash-babysitter from my childhood whom my mom now admits, "was always a bit odd."

My Career Disillusionment Theme Park would also feature this terrifying birthday-party-clown-slash-babysitter from my childhood whom my mom now admits, "was always a bit odd."

This formula is also known as the Roller Coaster of Self-Deprivation and Disillusionment. If you saw this ride at an Amusement Park, you would not get on.

But day after day, people choose to get on this ride.

The problem with this ride as a career approach is that it’s driven by violent swings of emotion and few facts. You're locked into the ride with no way off. 


Get on the Career Progression Choo-Choo Train

When trying out potential career options, you really want to be on the Career Progression Choo-Choo Train. You know the one. It ushers you around the park, letting you hop on and off at will. The whole point of the ride is to show you what’s out there. 

You ride it for a while, get the lay of the land, then strategically disembark at the places that interest you. When you’ve seen enough, you get back on the train. Whether you explore an area fully or just try it out for a bit, you know once you decide you’re no longer into it, the train is there to take you to the next cool thing.

Strategic. Smooth. Intentional.

This is how you want to approach your career. 

  1. Map out the interesting places in the Amusement Park of Work and Life

  2. Get on the Choo-Choo Train and survey what’s actually out there

  3. Hop off and talk to people, check out roles and organizations, see which ones are perfect for you and which ones are not

  4. Eat multiple funnel cakes

  5. Repeat

See the difference a little test drive makes? 


You Can’t Predict the Future, But If You Could, You'd Know This Approach Works

If I could predict the future, I’d be in a totally different line of business.

But I can’t. And I’ll bet you can’t either. 

So let’s get you on a path to proving out your career goals IRL.

Here's the story that made me remember this golden rule...

I started my business because I wanted to coach, write, and call my own shots. I didn’t particularly want to run a business. In fact, a lot of things freaked me out about it for so long that I justified staying in my corporate job for several years after I knew I didn’t want to be there any longer.

I worried about speaking and getting my name out there as an Introvert. I worried about not being able to figure out how to run the business side of things. I really worried about technology. I hate technology, and it overwhelms me.

Then this week, it happened.

Out of the blue, a big, complex, scary technology issue emerged. One that has serious Legal and Financial consequences if I don’t get it right. One that requires a ton of patience, decisions, and clearheadedness.

So, the other day I’m fully in it. I'm switching between two help desk chats, beta-testing new code, and scrawling out the work flow logic. My legs are aching and my knees won't straighten from literally not shifting positions for a solid 6 hours. Dehydrated, because I haven’t left the couch for a solid 8.

And I think, “I LOVE this. It’s so fun. Thank goodness I decided to do try out this running-a-business thing.” 

Now don’t get me wrong. I would definitely prefer not to deal with this type of issue ever in my life. But there are so many other boxes the business is ticking—values, purpose, challenging work—that this situation is actually enjoyable.

I could have let my fear of technology stop me from becoming a business owner. Instead, I gave it a whirl. I tried it. Very slowly at first. With each step, I told myself I could stop at any time.

But with each step, I wanted to know more, so I took more steps. I kept my corporate job. I didn't throw my life or career into chaos, but I steadily took steps to prove out whether running a business was something I wanted to do more of.

There were some parts that really scared me that weren’t that bad. And some things I never anticipated that I totally love.

It has stretched and expanded me in so many cool unanticipated ways, and I never would have gotten to this place if I hadn’t decided to give it a go. 

Here’s the thing. If I ever decide that I don’t want to run a business, I don’t have to. I can always get back on the Choo-Choo train, go get a job somewhere, and probably even find a fulfilling career working for someone else.

But I'm going to keep testing out the business thing until I prove it out, or it no longer makes sense to try.


Your Career Is Not a Lifetime Commitment

The same is true for your career. Get out of your head. Try it out.

It's not all or nothing. It’s not a lifetime commitment. It’s not even a month-long commitment. 

You don't have to give notice, forgo your paycheck, or jump straight into a new job to test it out. I don't actually want you to do it that way. It's stressful and high stakes and unnecessary.

Talk to 3 people. Spend a few weeks immersing yourself in that world. Take on a temporary project. Post your art online. Take teeny, tiny baby steps.

But you must actually try it.

Apply the golden rule of career change and advancement: You’ll never know until you try.

What are you ready to try?

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Author Bio: 

Before becoming a coach, Caroline spent 20 years in management consulting and financial services. She's made it her mission to help people grow, contribute, and get wherever they want to go.

Caroline wants women to recognize how much power they truly have to define their careers. The life and career you want really is possible once you have the roadmap. Take the first step by downloading her free guide.

She’s also a tennis fanatic, aspiring Minimalist, FIRE (Financial Independence and Retire Early) enthusiast, and Aloha Spirit seeker 🤙. She loves to share stories from her unconventional life and career focused on freedom, creativity, fun, health, family, and community. If she can do it, you can, too.