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Here’s Why Making Career Decisions Is Hard (& How To Make Them Easier)

Why Making Career Decisions is Hard Red Cape Revolution

Let’s face it: when it comes to making career decisions, even the sharpest among us can struggle.

struggling with career decisions? read on

Yes, even when we’re lucky enough to choose between something great and something equally great, we swirl and spend endless joules of human energy worrying about our decisions, sometimes giving up and just deciding to make none at all.

Why do we struggle with making career decisions?

Here’s my theory:

We struggle because we don’t understand the truth about how career decisions are made.

And once we know what’s true, we can move faster about the business of making career decisions—decisions that are right for us.

I developed this theory after reviewing hundreds of my client stories as I worked on my book about what to do when you hit a career crisis. I also took a hard look at my own journeys toward making better career decisions, as well as the growing stack of behavioral science and motivational research in books and academic journals.

Those stories pointed me toward the truth.

Three truths, to be specific, as well as some lies we’ve come to believe.

Once you understand these truths, you can adjust your thinking about how you’re making career decisions that are right for you.

Plus, you can try out the success strategies I’ve outlined here.

Then, you’ll make your next career decision faster, easier, and with less stress and worry.

Let’s get started.

Truth #1: You already know how to make decisions (so stop believing that’s a barrier)

If you follow the average professional human around for a day, you’ll find that s/he makes decisions all the time.

we make decisions all the time

Hit snooze, or get moving? Red shirt, or the white? Brew my own, grab Starbucks, or brave the office caffeine sludge?

In fact, some studies have quantified that we make about 35,000 decisions a day, even beyond the autobio decisions our bodies make for us (breathing, sneezing, cell-dividing, etc.)

How anyone attempted to count those decisions, I’m not sure. But no matter what the right number, it’s proof of one thing: you already know how to make decisions.

Maybe you’ve never realized that before.

Maybe you’ve been telling yourself the lie of “oh, I’m just not good at making decisions.”

Relax into the truth that you DO know how to make decisions and that on an average day, the majority of your decisions are working for you.

SUCCESS STRATEGY:  Catch yourself when you say or think, “I don’t know how to make a decision.” Say instead “I make decisions all the time, so I’ll figure this one out, too.”

This belief helps lessen the emotional pressure around the decision and builds your confidence that yes, you’ll be able to make a good decision.

In simple terms, when you hear yourself saying or thinking “I don’t know how to make a decision,” your brain is tricking you into what it thinks is safe—staying right where you are.

This is just biology.

Our brains are wired to send us messages that help keep us safe, like “back away from the dinosaur” or “avoid the hot flame.”

The problem is this primitive part of our brain hates anything unknown or unsure. Which, when we look at choices in our career and worklife, means almost everything other than what we know right now.

So you, as the adult in charge here, have to remind your brain of the truth–you DO know how to make decisions, and whatever the decision you make, you’ll be fine.

Because it’s the truth.

Truth #2: Your struggle is not about the decision, but about the consequences

When someone is stuck making a decision, it’s common to hear them say, “I don’t know what to do.”

Which I think is a perfectly acceptable answer . . . except that it’s completely false.

wait what about career decisions

Here’s why.

When you’re making a career decision, you typically start off evaluating two things: this OR that.

  • Stay here OR leave.
  • Work toward the promotion OR stay in this role I already like.
  • Take the job offered OR wait.
  • Seek out new opportunities OR risk that I’ll be downsized when the acquisition is complete.

And while it’s true that sometimes you’re choosing among multiple options (for example, stay and change, stay and wait, or leave now), most of the time our decision is binary.

So, if we’re getting honest here, we’ve got the WHAT part of the equation is handled.

You do know WHAT to do. It’s this OR that.

But what stops you from making career decisions is that your brain automatically spirals toward what happens after the WHAT: the consequences.

So it’s not the decision we need to focus on.

It’s understanding the consequences of our options.

Success Strategy: Get specific about the consequences of both options.

We humans are assumers.

To keep traveling quickly through life, we make assumptions about things we think we know. We take shortcuts, read clues and cues.

It’s one of our survival mechanisms.

survival is behind our career decisions

And it gets in our way.

When we’re making a career decision, we can get a little lazy and too often assume what the consequences will be like. For example, I’ve heard these pronouncements:

  • “If I work in a consulting firm, I’ll be traveling all the time.”
  • “If I move to a new state, I’ll lose money on my house now.”
  • “If I leave my job after being here ten years, I’ll screw up my retirement.”
  • “If I start something new in my 50s, I’m starting at the bottom again.”

To which, when wearing my coaching hat, I always reply, “How do you KNOW?”

(Typical response: crickets.)

We need to be a scientist of our situation and keep researching the specific facts and evidence about the consequences of each choice.

But how?

Here’s a secret: the best research is done by asking. 

And listening. And you know how to ask and listen, right? No new skills required.

And let’s ask real qualified people—not Google, Siri, or Alexa, and not just the noisy or nosy people in our lives.

A qualified person is someone who’s been there, done that.

Or even IS there, doing that.

Where to find them? Just look up and around.

Your friends and colleagues are great places to start.

  • “Hey–you work in consulting! How often do you currently travel? What’s it like? What do others do in your firm?”
  • “I know you moved to a new state for work last year. How did that work out for you? What was it like selling your home here?”
  • “I’d love to connect with someone who went to a new company later in their career. Who might you know who you could introduce me to for a chat?”

(Note: to help me make big decisions, I also use LinkedIn as a way to figure out who’s out there who I already know. Then I reach out and ask questions of them in real life. If you’re not actively using LinkedIn, read my article Why LinkedIn Matters (Even When You’re Not Changing Jobs) and get started now.)

Turn your assumptions into proven data by asking good questions of qualified people, most of whom you probably already know or can easily reach.

In most cases, once the consequences are clearer, your decision gets clearer, too.

Truth #3: In an age of openness, we’re still closeted about making career decisions

When making decisions about the movies we see, the food we eat, or the stuff we buy, we freely ask our questions in public.

We don’t hesitate to ask family, friends, and even those who are practically strangers on Facebook or specific topic forums:

  • Our vacation house has to be steps from the beach.
  • I need it to be fragrance-free, not unscented.
  • Which theater has the best nachos in their VIP section?

But asking in public is less common when we’re making career decisions, especially when you are a successful professional whose life already looks good from an outsider’s perspective.


Why do we keep this important decision-making process so private?

Well, some clients tell me, “I’m afraid my boss will find out that I’m not happy.”

[Which is silly, because if you’re not happy, you should be having a conversation with her about it, rather than assuming (there we go again) that she’ll figure it out and take some action. ]

Or, others say, “I don’t want to talk to anyone about it until I know what I want.”

[Which again, is goofy, because how can you know what you want if you aren’t talking to others to explore what’s out there beyond your current field of vision?]

But these aren’t the only reasons we keep our career decision-making quiet.

We stay quiet because we’re ashamed we can’t figure it out on our own.

We think our decision should be obvious, logical, rational.

We think the pros and cons will reveal all.

We think, “Hey, I’m smart—I should be able to figure this out.”

And then, when we can’t, we stay stuck.

And then we tell ourselves, “If I can’t make this career decision, there must be something wrong with me.”

Bumper sticker time: THERE’S NOTHING WRONG WITH YOU.

There’s no need for shame, embarrassment, or any negative emotion here. Making career decisions –especially big ones —is something most of us don’t do each day. It’s something we have to learn from others.

Imagine you’re watching a baby crawl. You wouldn’t say, “Oh, hey, you can’t walk yet? What a loser! Give it up and resign yourself to a life crawling on the ground.”

No. You help him up. You hold his arms while he waddles toward you. You shield him from sharp objects in his path.

The baby feels no shame that he can’t walk yet.

And you as his support system feel great when he takes his first steps alone.

baby walking

Success Strategy: Break the shame cycle, stop struggling and ask for (or accept) help.

A few years ago, I coached groups of up-and-coming leaders within a global technology firm. They’d take turns sharing their workplace challenges, and I’d coach and by example help teach the others how to coach their peers.

Our coaching was pointed toward action. (It still is.) That means we’d often wrap up our conversations by answering, “What’s the one thing you need to do NOW?”

One day I noticed a pattern.

No matter what the topic, one of the first actions that always emerged after someone was coached was “talk to my manager.”

And those actions always got them in motion, because either a) the manager could help, or b) the manager couldn’t but led them to the next conversation.

Plus, c), they got over their reluctance to talk about what was going on and what they wanted differently in their career.

The more we share about our career needs, desires, dreams & direction, the clearer the steps we need to take become.

If you don’t tell anyone you’d like to drive to Atlanta, no one is ever going to point you to the on-ramp for I-75.

If you don’t tell anyone you’re hungry, no one can invite you for a meal.

And if you don’t tell anyone you’re headed toward Atlanta and you’re hungry, they can’t tell you to exit at North Avenue, pull up at the Varsity and eat the chili cheese dog with a Frosted Orange.


So start talking. Gather a friend or two for lunch and bravely share the career decisions you’re considering. Chat with a colleague on LinkedIn, or talk to a professional coach or mentor.

Ask for help. There’s no shame in it.

And that’s the truth.

Hey—want more help?

No matter what’s happening in your career, a 30-minute chat with me can show you how to get out of a funk and move forward, fast.

Just hit the button below, and pick a date and time that’s available. There’s nothing to prepare–just show up right where you are. If, after we talk, it sounds like one of my coaching programs or courses will help you going forward, I’ll share details after our call. There’s no pressure—my goal is to be helpful immediately.

Spots fill up fast, though, so schedule yours now and start getting the support you deserve.

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