Ep 34 | The Next Step for People Who Are Winging It Well
What if your six-figure income, Roth IRA, and decent savings still aren’t giving you the clarity you want with your money?
In this episode, Priya speaks directly to the high earners who are “winging it well” (doing fine on paper, but feeling low-key uncertain under the surface). She explains why traditional financial advice (like risk tolerance questionnaires and chasing market returns) misses the mark, and how goals-based financial planning changes everything.
You’ll hear why having a financial plan isn’t about restrictions. It’s about freedom: like knowing you can drop $20K on a Maldives trip and still retire early. Or confidently skipping a concert, knowing your money’s already doing what it’s supposed to.
If you’ve ever thought, “I make good money, I just don’t know if I’m doing the right things with it,” this episode will feel like a wake-up call and a relief all at once.
Tune into this episode to hear:
Why traditional advisors still ask the wrong first question
What to do after you've been “winging it” successfully
How goals-based planning changes your relationship with money
The emotional freedom that comes from knowing what “on track” looks like
Follow Priya Malani:
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THE STUFF OUR LAWYERS WANT US TO SAY: Stash Wealth is a Registered Investment Advisor. Content presented is for informational and educational purposes only and is not intended to make an offer or solicitation for any specific securities product, service, or strategy. Consult with a qualified investment adviser (that's us) before implementing any strategy. Investing involves risk, including the loss of principal. Past performance does not guarantee future results. There…we said it.
Transcription
How much more freeing is it to know that you can take a $20,000 trip to the Maldives and you're still on track for retirement?
You stop reacting to every bit of news or advice you get because you have a strategy you trust. When your investment strategy is built around you—your goals, your timeline, your values—you finally get to feel confident that your money is doing what you want it to be doing.
And that's not just building wealth. That's the feeling of financial freedom.
Welcome back to The F Word, where I help ambitious 30-somethings get their financial shit together so they can live well now and build wealth for later.
Today I am talking to you if you're doing fine. You've got savings, maybe even a Roth IRA. Maybe you've bought a home. You're not in financial distress—but you're winging it.
Obviously, you're winging it well. The good news is: it's working.
But today I wanna talk to you about something that everyone's doing and no one's talking about.
And by “everyone” I mean your friends making a quarter mill working at Google, Meta, Delta, Intuit. They have a financial advisor. At the very least, they have a plan.
I get that you might be avoiding the financial benefit that your HR team offers up to you, but I promise you: once these people are making a solid six-figure income, they have a voice of influence on the money front.
Now, I'm not saying whether or not that voice of influence is sound. They might be working with their dad's financial advisor. But they've got a plan.
They're just not talking about it—because we still don't talk about money.
Ask them.
I was in Atlanta visiting a friend a few years ago. We ended up at a birthday party for one of her friends in Grant Park, and we're surrounded by these gorgeous homes—$1.1, $1.2 million.
As I'm chatting, I'm learning: the wife works for Delta, the husband works at Porsche. Another couple—one was a landscape architect, the other was in real estate.
Bottom line: having your financial shit together isn't just reserved for people who wear Patagonia vests. This is not about “finance bros.” Other people are setting themselves up for success—they're just not talking about it. Because like I said, we don’t talk about money.
So today I'm talking to you—the high achiever who's doing well but quietly wondering if there's a better way to manage what you've built.
You know how they say, “We didn't come this far just to come this far”?
I wanna talk to you about what to do next when you're doing fine—so you don't look back in five years and think, Damn, if I had only gotten intentional sooner, I would be so much further ahead.
Let's get into it.
When I worked on Wall Street, there was one question that shaped the investment strategy for all clients: What's your risk tolerance?
This was considered the gold standard. It guided the entire portfolio and all asset allocation decisions—because the assumption was: the more risk you can stomach, the higher the return you might get.
At first, it made sense to me. But over time I realized something:
If someone said they didn't like risk, they had a low risk tolerance, their portfolio was automatically built to experience lower returns. It was almost like they were being penalized for being afraid to lose money, for not liking volatility.
Meanwhile, clients who could tolerate more risk were rewarded with higher potential returns.
There was no talk about what those returns would get them—or if they even needed to take on risk to accomplish what they wanted in the first place.
And that was the big disconnect. Nobody was asking what the money was actually for. Why were we even risking it in the first place?
I mean, the obvious answer is to make it grow. But next I wanna talk about why chasing returns or building wealth in an arbitrary sense is pretty much the worst reason to invest.
The problem with performance-based financial advice is this: when return is the only metric of success, everything becomes reactive.
Clients get frustrated that their portfolio isn't keeping up with the market. Advisors are constantly defending performance: the S&P is up X and you're only up Y—without ever putting that into the context of the client’s life.
Why does this happen? Because on Wall Street, you don't start with a financial plan. You don't start with a clear idea of what success looks like.
So clients end up feeling shortchanged—or like the advisor isn't working in their best interest. And advisors feel like they're losing trust… kind of because they are.
The whole relationship becomes about whether your portfolio is beating the market—instead of whether your money is helping you build a life you want.
One of the most powerful shifts we've made at Stash Wealth is moving the focus away from risk tolerance and toward goals-based planning.
It starts by asking: What do you want your money to do for you? What are the milestones you wanna hit in the next 1, 3, 10 years?
And not just the big ones like buying a home or retiring.
I’m talking about taking a sabbatical. Buying a Bellini sofa. Donating to a cause you care about. Buying an awesome piece of art because you spent the afternoon in Soho and fell in love.
Booking a private villa for your parents' anniversary. Getting VIP tickets for every concert you wanna attend this year without thinking twice.
If your money isn't helping you live the life you want, then what's it really doing?
I'm not saying you can't get far with winging it. To be honest, winging it can work for a while.
Most of our clients—before coming to us—have figured out things pretty well on their own. But they still have that voice in the back of their mind:
I don't feel like I'm doing too bad, but I definitely don't feel like I'm in control either.
Or I have no idea what “on track” even looks like.
Or everyone assumes I have my shit together because I make tons of money—but honestly, I'm just making it up as I go.
And there's only one thing that'll help those feelings go away.
If you're thinking any of these things, what you're missing is a clear, defined target. A goal.
Imagine running a business without OKRs. People are working hard, things are moving—but how do you measure progress if you've never defined what success looks like?
How can you even celebrate a win?
You can't. You're just working toward this arbitrary future without ever really defining what you want to accomplish.
Without clear goals, it's so easy to feel like it's never enough. No matter how much you save or earn, there's never a finish line—because the race was never mapped out to begin with.
That's exhausting. You'll always feel like you're chasing something if you don't define what it is you want.
Here's what changes when you build a financial plan—and begin investing based on your goals:
You stop second-guessing every move.
You stop hoarding cash “just in case.”
You stop feeling guilty when you spend, because you know what's already accounted for and what the trade-offs are.
How much more freeing is it to know that you can take a $20,000 trip to the Maldives and still be on track for retirement?
You stop reacting to every bit of news or advice you get because you have a strategy you trust. When your investment strategy is built around you—your goals, your timeline, your values—you finally get to feel confident that your money is doing what you want it to be doing.
And that's not just building wealth. That's the feeling of financial freedom.
Not to mention, when you do this with your partner (if you're in a serious relationship), it’s an epic conversation starter. It's also the first step toward designing a life that you're both excited to be on track for—and held accountable to.
If you're winging it well but ready for your next best step, I hope this helped you see the value of putting a plan in place.
Getting intentional is the same thing as setting goals at work. It's hard to celebrate wins when you don't define what you're working toward.
The most powerful financial plans don’t just grow your money. They give you clarity, confidence—and most exciting, they give you permission to enjoy your money along the way.
Please send this to a friend who's winging it well and needs to know about this as their next step.
And if you wanna take the next step and experience what it's like to finally put your money where your goals are, you should book a call and see if the Stash Plan is right for you.
Thanks for listening to The F Word. See you next time.
