One of the most common conversations Hilary has with people in their 50s starts with the same concern: “I honestly have no idea whether I’m on track for retirement.”
And often, that uncertainty is not coming from someone who failed to save. Many people asking this question have been saving consistently for decades and have accumulated meaningful wealth. The uncertainty comes from realizing they have never actually measured whether all that effort is going to produce the retirement they want.
In this episode, Hilary Hendershott explains why retirement planning should not begin with the question, “How much have I saved?”
Instead, it should begin with a better question:
How much will your retirement actually cost?
At Hendershott Wealth Management®, one of the first exercises we walk clients through is calculating their Annual Spending Number, or ASN. Your ASN is the amount of money your portfolio needs to produce each year to support the retirement lifestyle you actually want, not someone else’s version of retirement.
Once you know your ASN, retirement planning becomes much clearer. You can begin answering the questions that actually matter:
How much do I really need?
How close am I today?
And if there is a gap, what is the smartest way to close it?
Retirement is not a pass-or-fail exam. It is a planning problem, and planning problems usually have multiple solutions. Those solutions may include saving more, improving your portfolio, adjusting spending, improving your tax strategy, delaying Social Security, or realizing you are closer than you thought.
The goal is not to convince you that you are ahead or behind. The goal is to replace uncertainty with clarity.
Download our free retirement guide today to calculate your ASN, estimate what size nest egg may support it, and evaluate whether you are on track.
Download the retirement guide:
Hendershottwealth.com/retire
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Here’s what you’ll find out in this week’s episode of Love, your Money:
- 00:45 Is it too late to catch up on retirement savings?
- 01:44 The better question to ask before retirement
- 02:24 What is your Annual Spending Number?
- 03:03 How to close a retirement savings gap
- 03:39 Why clarity replaces uncertainty
- 04:28 What the retirement guide will help you calculate
- 05:15 Download the free retirement guide
Resources and Related to Love, your Money Content
- HerMoney & Alliance for Lifetime Income (2024 Women, Money & Retirement Study): https://hermoney.com/invest/financial-planning/yes-even-higher-earning-women-worry-about-money/
- Mutual of Omaha (2025 Women’s Confidence and Retirement Survey): https://www.mutualofomaha.com/advice/financial-planning/build-your-financial-future/financial-confidence-lower-among-women-new-survey-shows
- InvestmentNews: https://www.investmentnews.com/retirement-planning/women-are-wealthier-than-ever-so-why-do-so-many-feel-financially-insecure/261200
- Standards Board for Financial Planning 2025 Research: https://www.standard.com/eforms/25463.pdf
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Transcript
[00:00:44] Hilary Hendershott: One of the most common conversations I have with people in their 50s starts like this, “Hilary, I honestly have no idea whether I’m on track for retirement.” What’s interesting is that they’re usually not people who failed to save. In fact, many of them have been saving consistently for decades and have accumulated substantial wealth.
[00:01:05] The uncertainty actually comes from somewhere else. See, they’ve spent years working hard and saving consistently. Then one day they realize they’ve never actually measured whether all that effort is going to produce the retirement they want. And that’s when the questions start, “Uh, have I saved enough? Am I behind? Is it too late to catch up?”
[00:01:26] The good news is that most people asking those questions don’t actually know yet whether they’re behind. They simply haven’t measured yet. So, today, I want to show you how we help people answer that question. I want to talk to you about whether it’s ever really too late to catch up on retirement savings.
[00:01:43] So, the biggest mistake I see people make is assuming retirement planning starts by asking, “How much have I saved?” But I don’t think that’s the right question. At Hendershott Wealth Management, we start somewhere else. We start by asking, “How much will your retirement actually cost?” Because until you know the answer to that question, you don’t know whether you’re ahead, behind, or exactly where you need to be.
[00:02:07] I’ve worked with people who were convinced they had fallen years behind, only to discover they were much closer than they realized. I’ve also met people with several million dollars saved who weren’t as prepared as they thought because they had never really estimated what their retirement lifestyle would require.
[00:02:24] That’s why one of the first exercises we take clients through is calculating what we call their annual spending number, or ASN. Your ASN is just the amount of money you’ll need your portfolio to produce each year to support the retirement lifestyle you actually want, not someone else’s version of retirement. Yours.
[00:02:44] For one person, that might mean traveling extensively. For someone else, it might mean spending more time with family, helping children or grandchildren, giving generously, or just enjoying a slower pace of life. Every retirement is different, so of course, every ASN is different. Once you know your ASN, retirement planning becomes dramatically easier because you can finally answer the questions that actually matter.
[00:03:13] How much do I really need? How close am I today? And if there’s a gap, what is the smartest way for me to close it? And that’s where people usually begin to feel hopeful again because retirement is not a pass or fail exam. It’s just a planning problem, and planning problems usually have multiple solutions.
[00:03:33] Often, we can improve your expected investment return by building a better portfolio. Sometimes the answer is saving more. Sometimes it’s working another year or two. Sometimes it’s making thoughtful adjustments to spending. Sometimes it’s improving your tax strategy or maybe delaying Social Security, and sometimes it’s simply realizing you’ve been comparing yourself to generic retirement advice instead of your own financial plan.
[00:04:02] Especially among successful professionals, I’ve found that uncertainty is much scarier than reality. Once people understand their numbers, the uncertainty starts to disappear. They stop comparing themselves to rules of thumb and online articles. They stop wondering whether they’re behind, and they start making decisions based on a plan that’s designed specifically for the life they want to live.
[00:04:27] That’s exactly why we created our retirement guide. It walks you through calculating your annual spending number, estimating what size nest egg is likely to support it, and using our retirement calculator to evaluate whether you’re on track. It also covers many of the retirement planning risks people often overlook, including inflation, taxes, healthcare costs, sequence of returns risk.
[00:04:54] It also includes checklists for people who are roughly 25, 15, or five years from retirement. My goal isn’t to convince you that you’re ahead or behind. It’s to replace uncertainty with clarity because feeling behind and actually being behind are two very different things. Until you’ve done the planning, you simply don’t know.
[00:05:15] So, if you’ve reached the point where you’re wondering whether you’ve saved enough or whether there are still opportunities to strengthen your retirement plan, I encourage you to download our free retirement guide today. It will help you understand where you stand today, identify your highest priorities for improvement, and see new possibilities for the future that you may never have imagined on your own.
[00:05:39] Because retirement isn’t about reaching someone else’s number, it’s about building enough financial resources to support the life you want to live. Download our retirement guide today by clicking on the link in the show notes below this video.
Disclosure:
All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful. Advisory services provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.
All video and written content is for information purposes only and does not constitute an offer, or solicitation of an offer, or any advice, or recommendation to purchase any securities or other financial instruments–and may not be construed as such. Opinions expressed herein are solely those of HWM, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. HWM does not provide tax or legal advice.

