Hey,

I meet a lot of people who have convinced themselves they’re perfectly fine with the limitations their income places on their lives.

I’ve also met tons of “ostriches” — people who keep their heads in the sand when it comes to personal finance. 

Inevitably, some of those people make huge financial decisions (like buying a home) even when it’s not the right move for them.

I’m not against buying. I’m FOR running the numbers!

And I get it. It’s easier to avoid confronting our money problems. It’s really hard to admit when we’re not content with our life or we’ve made a mistake. Because then we have to make a choice: 

Do something about it,
or keep knowingly doing the stuff that’s making us unhappy.

There are so many ways to dance around the knowledge that you want more: more money, more free time, more agency over how you spend your time.

It’s human to avoid hard facts like this! When we feel powerless, it hurts less if we avoid looking that powerlessness right in the face. Since you’re subscribed to this newsletter, I know you’re not afraid of growing, even if it’s uncomfortable. But what about the tricky times when you don’t even realize you’re feeling bad?

(A coach and close friend of mine has a folksy saying for this: “It’s hard to read the label when you’re stuck inside the jar.”)

So today, I’ve got a few questions for you to help you figure out if you’re truly content — or if you’re secretly trapped inside a life with boundaries you’re not seeing.

7 questions to figure out if you’re trapped 

Let’s turn this into a game. You start with 7 points. Subtract 1 point for every “Yes.”

1. Do you hesitate before ordering appetizers, drinks, or dessert?

This is one of the most common signs of financial pressure. Adopt this habit and before you know it, you’re nickel-and-diming fried pickles and secretly hoping your friend will pick up tonight’s tab.

Cue the resentment, the self-righteousness, and the sudden splurges that you have to “make up for” later.

2. Do you check your bank balance daily?

Not because you’re worried about going completely broke. But because you see your self-worth reflected in the numbers in your account.

When your bank balance is “high” (whatever that means to you), you feel safe. In control. Virtuous, even.

But when it’s low, you start to feel nervous or overwhelmed. And you start asking: How am I going to get back in control?

3. When your alarm goes off in the morning, are you flooded with anxiety?

Whether you think of this phenomenon as Morning Dread or the Sunday Scaries, getting walloped by your nervous system mid-REM cycle is no way to wake up.

If returning to the waking world just makes you want to go back to sleep, you’ve got a big problem.

Believe it or not, some people feel GOOD about work.

4. Did you leave your work phone, Slack, or email inbox on or open during your last vacation?

Tell me if this sounds familiar: You put in your hours at the office week after week, and plan exciting vacations to exotic places to “finally relax.” But then as the days count down to your PTO, you paradoxically feel MORE stressed, because you know you won’t be able to truly unplug.

My opinion? If you can’t toss up a carefree OOO message without spending your whole trip worrying about the mountain of work waiting for you, you’re more trapped than you think.

5. Do you resent people who have “more” than you?

Take a second to open Instagram (I’ll wait). Spend 30 seconds scrolling, then come back.

…how do you feel?

If you instinctively reacted with bitterness or jealousy to your friends’ happiness and achievement, that’s a decent sign you’re feeling unfulfilled.

6. Do you wish you could be working on something you love, instead of working just for the paycheck?

If you said no, you might just be really happy in your job (and that’s amazing).

But in my recent reader poll, 90% of you said you wanted to start your own business.

Even though 90% is an incredibly high number, I’m not surprised. Most people long to have more control over their work, their schedule, and their income.

7. When you think about spending the next 5 years doing what you’re currently doing…are you tempted to leave it all behind and flee to the forest, a van, a Tibetan monastery??

I know this is a tough question to answer, since we’re famously bad at forecasting what will make us happy.

But if you really think about your daily routine, and imagine yourself doing it 5 or 10 years from now…how do you feel?

How many points did you end up with?  

If you’re still at 6-7 points, you’re doing great. There’s no sense that something is wrong or broken. You’re genuinely happy with what you’re doing. Love that for you.

Carefully clapping so I don’t hit my mic

If you’re at 4-5 points, well…there’s room for improvement, right?

And if you ended the quiz with 1-3 points, first, I want to thank you for owning up to some seriously uncomfortable feelings. 

You know what I’m going to ask next. 

What are you going to change to get back to 7?

And look, . My goal with this email isn’t to make you feel hopeless. It’s to help you honestly evaluate your life as it is right now, so you know how it stacks up against what you want. That’s the first step toward GETTING what you want. 

P.S. I’m doing a free live class soon, all about how 42,000+ people have improved their scores on this quiz. Check your inbox tomorrow for more info and the session sign-up link.

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