How Well Do You Prepare For The Success You Want?
My definition of “success” is simple: having what you want on your own terms — without doing harm to others, of course.
I move through the world presuming that everyone wants to be successful. In fact, my work (coaching, speaking, and creating content) is grounded in helping people be, “successful, profitable…and not broke.”
I’ve been doing this work for decades, partnering with professionals across industries and the income and wealth spectrum. And I can confidently say, many of us (yes, myself included), don’t always prepare for the success we say we want.
You and I work “hard” (there’s that word, again), and when the fruits of that labor, time, and energy start to show - more clients, more income, more opportunities, increased visibility — everything looks great. On the outside.
But it’s a different story on the inside.
You’re exhausted.
Revenue looks good, but cashflow sucks.
You’re grateful for your new level of success whilst quietly wondering if you can keep pace with all the new opportunities coming your way.
In other words, success on the outside and stress on the inside.
Mask of Success
That’s what I call the mask of success — when the story everyone sees doesn’t match the one you’re actually living.
Can you relate? Have you ever hit a milestone you were aiming for only to end up feeling uneasy beneath the surface?
And it’s not just theory — I’ve seen this play out with clients at every stage of their careers.
Joshua has: his company finally hit the $10 million mark — an incredible milestone, indeed. But this achievement felt “heavy,” something he wasn’t expecting.
During our conversation a few years ago, I shared with him how, whether you grow a business to half a million, a million, or $10 million, what comes with that growth is that your roles and responsibilities — along with the expectations others have of you — change.
Navigating and negotiating these shifts is something you also bump up against as you achieve the success you want.
That’s why I feel confident in saying: we all have experience dealing with this mask — because it stems from a mix of pride, self-protection, and social conditioning.
We want to look like we have it together.
And this is not entirely a vanity exercise. I mean…have you or anyone you know hired or invested in someone who doesn’t seem to have “it together”?
Same for letting people see you struggle.
Everyone struggles with something. You and I know this in theory. But, I bet you’re guarded about whom you let bear witness to how you navigate the vicissitudes of life and business — your process of “figuring it out.”
Based on my own experience and observation, I’d say being protective is smart and strategic — especially given how judgmental some folks can be. (Remember my story of the person who said they didn’t hire me because I don’t own my apartment?)
And, we can’t overlook a cultural and societal reality: very often, it’s not safe (or is taboo) for some folks to express any vulnerability whatsoever. We have plenty of examples of how person “A” can fail and be given another chance, whereas person “B” is not afforded the same grace.
From my perspective, the mask of success isn't inherently “bad.” It’s just a signal.
It tells you something about what you’re trying to preserve or avoid revealing.
And, as far as I’m concerned, you have every right to use this as a tool to hold onto or reclaim your power.
But, Let’s Unpack the Cost
That said, I’d be remiss if I didn’t talk about the emotional and practical toll of donning the mask of success. You pay the price in three key ways:
Keeping up with appearances can be exhausting! While everyone isn’t entitled to know all the details of what’s happening in your life and business and with your money, I hope you’ve curated a trust circle where you can safely put down your mask.
Being overly guarded can lead to lost opportunities for connection and support.
Not minding the gap between the success others see and stress you feel on the inside can cause you to overlook how this friction is affecting your decision-making — in small and large ways.
Let Your Mask Prepare You
If you’re projecting financial ease or business growth while quietly managing stress, debt, or uncertainty, I see you.
If you’re managing a health crisis, while keeping your team intact and your clients satisfied, I see you.
If you’re managing a career transition that you’re keeping close to the vest, I see you.
Or maybe you’re quietly holding two realities: everything’s growing on the business front, but something else in your personal life is failing.
These are not made-up scenarios; they’re taken from real-life situations. And if you see yourself in any of them, please know this: your mask is a shield. It’s trying to protect you.
However, my hope for you is that it doesn’t become a barrier to enjoying the success you’ve worked so hard for. And that you always remember this:
Success doesn't just change your circumstances — it requires that you change on some level, too.
This is what I meant when I said earlier that we don’t always prepare for the success we say we want.
It’s one thing to achieve a goal and get the outcome you envisioned. But you and I don’t always account for how we need to change once we get what we want.
More often than not, it’s because we simply don’t know what this new level of success asks of us — in terms of new roles, responsibilities, and expectations. Or how our mindset, habits, and choices might need to evolve.
So, what about you? Where might your own version of the mask be showing up — and what is it trying to protect?”
When the mask of success appears, it’s not a flaw — it’s a starting point for getting answers.
If you’re ready to explore what might be hiding behind your own version of this type of mask, that’s the kind of clarity work I do every day — whether through ongoing coaching or a focused 90-minute Clarity Session.
About Jacquette
I love to ask questions and spark aha moments. I love to talk about why success with money is about more than just the numbers, and how the cultural impact on the intersection of money, business, and life matters–A LOT! And, I really hope I help people feel seen, heard, and not judged—especially since money is emotional and personal.
