286 | Ask Hilary: Purpose, Pivots, and Permission to Stop Hustling So Hard

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Welcome to the first Ask Hilary episode, where we dive into real-world questions about money and mindset from listeners like you!

 

Today, we’re leaning into the conversation we started last week with Jeff Willmore about living true to your calling. We’re going to talk about what happens when you hit your financial goals, but something still feels… off.

 

These questions center around calling, career pivots, and permission to want more than just security. They are the kinds of conversations that move us from autopilot to intention, to help you make wealth-building choices that actually reflect who you are and what matters to you.

 

If you’re craving clarity, ease, or meaning in your money life, this one’s for you.

Here’s what you’ll find out in this week’s episode of Love, your Money:

  • 02:07 What if I’ve built financial stability—but don’t feel fulfilled?
  • 09:26 Can I pivot careers without starting over financially?
  • 16:09 Is it lazy to want more space and ease in my business?

Inspiring Quotes and Words to Remember

“Wealth can be about accumulation and I think if you're to watch The Wolf of Wall Street or the sort of traditional male egoic movies that tap into the zeitgeist that was, you'll see that more money is always better and money is about power. And a lot of women just don't experience it that way, and that's not what we're up for.”

“You have the opportunity to really live an aligned life… giving yourself permission to do that is synonymous with giving yourself permission to create boundaries, saying no to things.”

“You can build a business or career that reflects who you are, not just what the world expects.”

“I cannot promise your calling will make you rich, but I've seen it time and again that aligning your money with your purpose creates a deeper, more lasting kind of wealth.”

“Life is about what you do most of the time, not failing to do what you're committed to doing some of the time.”

“You have neuroplasticity. What feels impossible today will not seem impossible later.”

“We've definitely been taught that hustle, hard work translates to worthiness… you have to check the perception.”

“Redesigning your business or your schedule isn't a failure. That's progress.”

“The hidden cost of your burnout is very real.”

“The thing we don't give ourselves permission to do on a regular basis is reevaluate the list of obligations, promises, agreements, and encumbrances we've picked up over time.”

Resources and Related to Love, your Money Content

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[INTRODUCTION]

 

[00:00:34] Hilary Hendershott: Welcome to Love, your Money®, where we’re flipping the script on traditional financial advice. This is an Ask Hilary episode where I answer your real questions about investing, tax planning, money mindset, and more. Because Ask is one of the 7 Steps to Wealth, and whether you’re asking questions that help you learn more and empower yourself or seeking out the support you need to take the next step in your wealth-building journey, asking is an essential step to building clarity, confidence, and momentum with your money. Let’s dive in.

 

[EPISODE]

 

[00:01:10] Hilary Hendershott: Alright. So, this is the first episode of Ask Hilary, and today, we’re exploring what happens when you hit the goals you thought would make you feel more secure or successful. And you realize something still feels missing. Today’s questions center around your calling, your purpose, and permission to want more than just financial stability. Alright, first question. “How can articulating my calling help me in my wealth-building journey? Hilary, I’ve spent the last few years building financial stability, finally got out of debt, started investing, and even hit my income goals.”

 

[00:01:48] Go, girl. “But something still feels off. I’ve been so focused on checking boxes that I haven’t stopped to ask why I am doing any of it. How do I figure out what I’m really working toward? And can that actually help me build wealth in a more meaningful way?” Well, we are starting deep here on Ask Hilary, aren’t we? Yes. As we go around in life, as time passes, we tend to pick up jobs, partners, kids, sometimes divorces, houses, experiences, obligations, right? And then we forget to stop and think about them. In reality, we forget to do a life review and give ourselves permission to release those that no longer suit us or fulfill on our calling. The question really is why are you on the planet? What is it that most inspires you? What is it that you love doing most?

 

[00:02:42] What is your calling? What is your raison d’etre? For those of you listening who actually speak French, I will never say that right. And I just apologize from the bottom of my heart. It’s just the way that it is. But we all know what I’m talking about. It is, of course, important to know what your calling is. Mine is, “People are free.” And as I look over the course of my life, I can see many ways when I took serious forks in the road that deviated from the path more traveled and that have allowed me to build a life that I love. And of course, I’m always doing life reviews to see what I can release. For the most part, what I’m really good about releasing is physical stuff.

 

[00:03:25] I’m like in my house, I’m known as the woman who throws things out and gives them to charity. Whenever my daughter can’t find anything, she and my husband look at each other and say, “Maybe mama threw it out.” So, that’s just an example of how I remain free of encumbrances. And I just want to thank you for writing this question. Wealth can be about accumulation and I think if you’re to watch The Wolf of Wall Street or the sort of traditional male egoic movies that tap into the zeitgeist that was, you’ll see that more money is always better and money is about power. And a lot of women just don’t experience it that way, and that’s not what we’re up for.

 

[00:04:04] I don’t desire more power in my life personally, and I’m guessing if you’re listening, that’s not in your top three. You have the opportunity to really live an aligned life. And of course, giving yourself permission to do that is synonymous with giving yourself permission to create boundaries, saying no to things. Let me just give you an example. In my life, I have decided, and I have mass-marketed the idea that I don’t attend graduation ceremonies. I find they are uninspired, they’re boring, they are hot, they are bad for my skin. I don’t like crowds. And so, I’ve just made a rule. And what are the trade-offs? So, by the fact that I’ve made the rule, everyone knows it’s an even playing field.

 

[00:04:52] I say to people who I love dearly who are graduating. I love you. I’m so proud of you. I’m so happy for you. I’m not attending. You know I don’t go to graduation ceremonies. They go, “I know, Auntie Hilary. I know.” The trade-offs are they might be offended. They might be hurt. I might miss a great speech, right? We’ve all heard massively inspiring graduation speeches, commencement speeches. By the way, I hope you’re parlaying this answer into whatever the thing in your life that is the graduation speech. You parlay this into whatever you need to release, right? So, again, I’m just admitting there are trade-offs.

 

[00:05:25] Anytime you put a boundary in place, there are trade-offs. The big one usually is that somebody might be offended. You might have to quit a job. You might have to get divorced. You might have to rearrange your custody agreement. But what it provides for me is, God, I get just a ton of time back, and I used to dread those things. I used to dread them so much, and I’m just so happy for my life rule that I don’t attend commencement speeches. But let me just ask you, have you articulated your raison d’etre? I call it my calling. Have you articulated that? We want to look in the realm of the experience you’re most inspired by, most enlivened, most lit up by when it happens for you and other people.

 

[00:06:08] And the other people are definitely in there. It’s not just you, right? It’s not just, what emotions do I want to have? No, no, no, no, no. The emotion is very clear. It’s inspiration, right? And so, there’s going to be moments in your life when you were just lit up. And so, really look at what are the strings that tie those events together. And then, of course, you can build a business or career that reflects who you are, not just what the world expects. I recently had someone on my podcast who said that, “Manipulative behavior is when you do anything that attempts to control what other people think of you.” That was revolutionary for me. I thought, “What a great life motto.”

 

[00:06:47] And if you abide by that, if you really take that to heart, you have the opportunity to just live the life you love living. Hang out with people that resonate with you and with whom you resonate, and let the rest go. So, from my own experience, knowing my calling has shaped my business, my peace of mind, how I mother, how I plan my free time, right? It’s kind of everything. I mean, the best way to make sure that you aren’t filling your life with encumbrances; obligations, is to give yourself permission to release things, whole categories of things, right? I have decided I’m not going to learn to play pickleball. I’m just not. I don’t want to make the time right now. And I know myself, I’m competitive.

 

[00:07:36] How I would take that on is I would go spend an hour on the court every morning for three months, and I would be obsessed. And I’m just not going to carve that into my schedule right now. There’s pickleball for you. There’s commencement speeches for you, right? The things I’m saying, you have these examples in your own life. So, if this was your question, a life review is in order. I cannot promise your calling will make you rich, but I’ve seen it time and again that aligning your money with your purpose creates a deeper, more lasting kind of wealth. That’s real-life fulfillment. And you need both.

 

[00:08:15] You need fulfillment in the area of money and fulfillment in the areas of life, career, family, relationship to self, relationship to the world, really, in order to experience the peace of mind that most of us are seeking. So, kudos to you. You’re on the right path. It’s a big journey. You have a big job ahead of you, and it’s a process. It’s a constant gardening process, but I congratulate you for taking the first step.

 

[00:08:42] Okay. And as a segue to the next question, if your calling gives you direction, the next fear that surfaces is often this: What if it’s too late to change career paths? And this is my second question, “Can I pivot careers without starting over financially? Hilary, I’m in my early forties and I have a stable, high-paying job, but I’m exhausted, burnt out, and uninspired. I’ve been thinking about making a career shift, maybe even starting my own business. I’m scared that I will lose everything I’ve built. Is there a way to make a meaningful change without torching my financial future?” Yes. Let’s not torch anything. Definitely don’t torch things. Absolutely. Gosh, so many people have done this, right? You are not alone. It is so common.

 

[00:09:33] I did my MBA, I don’t know, 12 or 13 years ago. I feel like two-thirds of the students in the MBA program were covertly there because they hated their solo contributor roles at work, right? It’s very common. 18-year-olds aren’t qualified to select their own major in college, right, because they have no idea what they’ll do for the rest of their lives. It’s very normal, very normal. I’ve walked many clients through this process, okay? So, you definitely need a plan. That plan is the bridge between where you are and where you want to go. Hopefully, you can make that plan in partnership with your financial advisor. Don’t torch anything.

 

[00:10:10] And how we’re not going to torch things is we’re going to have kind of like a bridge plan. I’m reusing words here, but you want to take the time to minimize your expenses. I’m assuming. Let’s just take it simple. You’re going to quit one job and you’re going to either take some time and get trained to do another or go start in another role where you make less money, or you’re going to start a business. Those situations are basically the same. If you have the opportunity to go from $150,000 a year in comp to $150,000 a year in comp, in the beginning, you were doing something that didn’t inspire you, and then you shift to doing something that is, well, you don’t even need to talk about that. Just go do that, right?

 

[00:10:49] But that’s not why this person is writing in, and that’s not the situation most people have questions about. Here’s what we’re going to do, though. We’re going to take the time to minimize our expenses. Take stock–I say the same things over and over again–take stock of what you have and then look at how much you’re spending. How do you figure out how much you’re spending? Don’t get overwhelmed. Go into your bank account and download the last three months of statements. Your outflows over the last 90 days, multiply that times four, that’s your spending. Assuming you’re paying for credit cards, you’re paying off credit card balances from that same account, right?

 

[00:11:25] If you have more than one checking account, you need to download all of your checking accounts and sum the numbers. That’s your spending. We’re going to use tools and software, and apps to cut out subscriptions and recurring costs. If you can, bring in a roommate, someone who’s paying rent on that spare bedroom in your house, or you’re going to talk with your husband or wife about living on their income for three to six to nine months, right? Have an educated guess about how long it’s going to take you to get where you want to be. And then the planning fallacy says, “Double it.” You want to be prepared for more time off than you think, right?

 

[00:12:04] And I’m not kidding. The planning fallacy does say, “Double your estimates about how long it’s going to take to accomplish something.” You’ve built wealth, and it may feel like, “I can’t get off the treadmill. I cannot take this train off the tracks. I cannot stop maxing out my 401(k) contribution, Hilary.” But you can. You really can. Life is about what you do most of the time, not failing to do what you’re committed to doing some of the time. Honestly, I promise you, if you keep your financial rudder where it has been and just stay committed to getting this new career; this new plan enacted, eventually, it turns out. I’ve helped women model new career paths without sacrificing their financial security.

 

[00:12:50] All we do is babysit it closely, right? The world is your oyster in terms of if you are a person who can take a skillset or a body of knowledge out there. From out there, I don’t have that skillset, I don’t know those things, and you know how to bring them in here to where you do have that skillset or you do know those things, you can do anything you want. Okay. I didn’t start being a financial advisor until my late twenties, and I sat in meetings with my father for years. I mean, he was leading them.

 

[00:13:23] And then I didn’t choose to go out on my own for the sake of going out on my own. I chose to go out on my own because not going out on my own, staying in that job, was impacting my relationship with my now husband negatively because I was unhappy, right? And the only choice I saw in front of me was, “I got to go out on my own.” And I just figured it out. I just figured it out. I literally put blank contracts in my car and drove around to my existing clients–with my father’s permission–and got them to sign them, and every time they signed, I was surprised. Every time, okay? I’m not anymore. This never surprises me anymore, but you know, you have neuroplasticity.

 

[00:14:03] What feels impossible today will not seem impossible later. Just think about all the things you’ve mastered. So, no. In summary, this can be accomplished with a plan, consistent, good intentions, motivation, right? You just keep those things in place. If you’ve been a person who’s been on track financially and committed to that, that’s not going to change, right? We have many clients who have spent years earning between $250,000 a year and $750,000 a year in total compensation get completely burned out. They go make $105,000 for a couple of years, right? Because they have life balance. They don’t have toxic work environments anymore. They like their coworkers.

 

[00:14:47] These are all things we’re fans of, and their financial plans are chef’s kiss, no problem, never got off track. So, if I haven’t already said this, I have faith in you. Make a plan, remain diligent, stay the person that you are, and just put one foot in front of the other. But once you’ve decided that your personal fulfillment on the planet; your life fulfillment; your happiness is more important than the things you decided to chase 10 and 20 years ago, make the change. That’s what life is about. So, more power to you, and hopefully you’ll check back with me in a year and tell me it all worked out. I am complete. Okay. And then for folks who do take that leap, you decide happiness is more important than the corner office, then this next feeling tends to creep in. Is it okay to want ease?

 

[00:15:39] So, this is the third question for today’s episode. “I feel guilty for wanting more ease in my business. Am I lazy? Hilary, I built my business from the ground up. It’s profitable and I’m proud of it, but I’m tired. I keep dreaming about more space in my life, but every time I think about slowing down, I feel guilty. I feel like I should be hustling harder. Is that normal?” If it’s not normal, then I’m not normal. I feel like every major transition in my business has been precipitated by this feeling on my part. If you wrote this question or if you’re listening to this episode and you’re asking this question, yeah, this is to be human. Nobody likes to feel like they’re carrying the weight of the world on their shoulders.

 

[00:16:28] For many of us, we come out of college motivated, ambitious. If you didn’t go to college, high school, whatever it is. We come into the work world motivated, ambitious. All you have is your time and resources, right? You got no money in the bank. You’re not sure how much money you can make. You’re not sure what you’re worth in the marketplace. You’re like, “I’ll trade anything.” Very normal. And then you pick up a job, and then you pick up a romantic partner, and then you have a kid or two or three, and then maybe your mom or dad gets sick and life gets really complicated.

 

[00:17:01] Life gets hard, and you’re going to want to unburden yourself of some things. I think that we’ve definitely been taught that hustle, hard work translates to worthiness. I fall victim to this all the time. I sometimes find that I don’t really want my team to know if I’m taking time off in the middle of the day because I’m afraid if they know that I need to rest that they won’t work. I mean, it’s just crazy the things my brain tells me. That’s why you have to check the perception, right? Is this an evidenced assertion that my brain is telling me? Is my mind telling me reliable things? This is a conversation I have with myself often.

 

[00:17:38] Paying people a great wage and bringing them into my company to do things that I’ve been doing, and then inevitably discovering that in some cases, they do it much better, is how a business grows. That’s called the evolution and growth, and scalability of a business. Redesigning your business or your schedule isn’t a failure. That’s progress, right? You want to move to elevate and ascend in terms of the things you’re accountable for, what your perception is on, and what you’re managing. Unless your business is shrinking in size, you are managing a business every day that you don’t know how to manage, literally. So, this saying, I wish it was more poetic, but it’s “new level, new devil.”

 

[00:18:24] Every time your business grows, you’ve got to solve new problems. And in businesses, mostly that means focusing on profits so that you make more money, more sums of money, so that you can continue to hire people and build a team and delegate off of your plate. That’s how you know you actually have a business. If you’ve read The Entrepreneurial Myth, The E-Myth book, you know that a business is a machine that produces profit consistently, and if it’s you that’s producing the profit, you don’t have a business, you have a job. In other words, lawyers charge $650 or $850 or $2,000 an hour because they don’t have businesses.

 

[00:19:02] Technically, a lawyer has a job. And because they’re the ones producing the work that they charge for, they have to charge an S ton of money because they also have to live. They have to go on vacation, they have to get their nails done, they have to take care of their kids, they have to sleep, right? And they have to make a good amount of money. That’s why pricing matters, but that’s a different question. The hidden cost of your burnout is very real. Over the years, when my daughter was sick, I didn’t know how to say no to things. Definitely was burned out, and my body is still suffering consequences. I am not the physical athlete that I was. I don’t know if or when it will come back, but I’m working on it.

 

[00:19:49] But I have to acknowledge that me driving past what I felt was comfortable or what I was capable of for so many years. It hurt me. It hurt me, and it can hurt you too. And the truth is now that I’m taking steps back, I can set my mind to work on more complicated questions. I can show up better on social media. Well, circling back to setting my mind to work on complicated questions, my mind solves complicated problems. And you can’t do that when you’re stressed, burned out, running from thing to thing, right? So, time, space, white space on your calendar leads to more creativity, not less.

 

[00:20:28] So, the only kind of tweak I would make in your mindset, if this is a question of yours, is set your intention that spending less time in your business actually leads to more money. There is no reason that can’t be true. It just requires new thinking. To go back to quotes I don’t think are very poetic, but there is a quote. I think this came from Brendon Burchard, and he said, “If you want something new, something new has to come out of you.” And so, what you’re asking for, if this is your question, is for something new to come out of you. And we assume that we’re working so hard.

 

[00:21:09] And so, if we want to work less, of course, that’s going to mean less money. But the only thing that’s required is different thinking, different agreements, different arrangements, different product lines, different profitable revenue streams. Different ways that your team supports you, different people on your team, whatever that is, it’s unique to you. But I wouldn’t start with the assumption that working less necessarily means less money for you. Your business should be the golden road to an amazing lifestyle. It really should. Running a business is fun. It’s hard. It’s hard work, but it’s fun, and it should give you the ability to engineer your life. So, congratulations on having something exciting that you want to engineer and just watch your assumptions as you go about redesigning the way that you work so that you can have the life you most want.

 

[00:22:01] All right. Thanks for listening to this episode. These are really the kinds of questions that move us from autopilot to intention, living a life of intention, right? So, once you’ve articulated your calling, I mean, look, as you’ve been going along in life, you’ve naturally been making choices that’ll align with your underlying principles and values. That’s what we all do. It aligned with your life the day you made that choice. The thing we don’t give ourselves permission to do on a regular basis is reevaluate the list of obligations, promises, agreements, and encumbrances we’ve picked up over time. Okay?

 

[00:22:39] So, that’s one of the themes of today’s questions; today’s episode is permission to review, augment, edit, and delete. Whether you’re just beginning to explore your calling or wondering if it’s too late to change course, you’re not alone in those reflections. And if something in your financial life feels off, it’s worth listening to that nudge. I am complete. Thanks for listening to this Ask Hilary episode of Love, your Money®. If you’re ready to get intentional with your finances, I recommend you start with the framework we use with our clients and in our own lives every day, The 7 Steps to Wealth. You can download the free guide at HendershottWealth.com/7Steps. That’s the number 7 steps.

 

[00:23:22] And don’t forget, you can send your own Ask Hilary questions to hello@hendershottwealth.com or just go to HendershottWealth.com/AskHilary. Until next time, keep loving your money so it can love you back.

 

[END]

Disclaimer

Hendershott Wealth Management®, LLC and Love, your Money® do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.

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