If retirement is approaching — or even if it’s decades away — the time to plan is now. From financial requirements and lifestyle needs to where you’ll spend your golden years, the number of decisions that have to be made can be overwhelming.

We reached out to a number of experts to learn more about transitioning to retirement. Our panel:

Diane DeStafano, senior financial advisor, Ledyard Financial Advisors. ledyardbank.com Jay H. Levy of Measured Wealth Private Client Group LLC, and author of “Planning for Survival, The Great Retirement Conundrum.” measuredwealth.net Cathleen Toomey, vice president of marketing, The RiverWoods Group. riverwoodsgroup.org Diane DeStafano, senior financial advisor, Ledyard Financial Advisors. ledyardbank.com

I’m thinking of retiring within five years or so. What should I be doing to prepare for this transition?

DeStafano: “In order to head into retirement with confidence and comfort, knowing that you’ve prepared yourself financially for that big day, you must take an honest look at your finances. One of the critical pieces of the puzzle is understanding your cash flow, which is the inflow and outflow of your money — your income and expenses.

“You’ve probably said at some point, ‘Where does all of my money go?’ The best way to understand where it all goes is to track your cash flow, even if it’s for just one month. There are many different apps available (Mint, Goodbudget, Clarity Money, Every Dollar, for example) and spreadsheets to assist you with this process. Understanding your cash flow while you’re still working will help you to realize what, if any, adjustments need to be made to your spending prior to retirement. You may find that in retirement you spend less on your wardrobe, lunches and commuting expenses. While other retirees find that they spend more in retirement by taking up a new hobby or sport or traveling more frequently.”

Will I still need an emergency fund in retirement?

DeStafano: “Yes, it’s so important. I encourage clients to keep at least six to eight months of living expenses in an account that is liquid and safe. That may sound like a boring investment, but emergencies can arise at any time. Having the funds available to cover the emergency will ensure that you avoid having to sell invested assets (which could create a capital gain or loss) or tap into retirement assets (which might mean creating taxable income).”

What can I do now to save more for my upcoming retirement?

DeStafano: “Once you have a good handle on your cash flow, it’s equally important that you’ve made saving for retirement a priority. If you are still working and your employer offers a 401(k) or 403(b) plan where you work, be sure that you are contributing at least up to the employer match. This is essentially free money. Your employer can automate the saving process for you by having your contributions come directly out of each paycheck.

“For 2021 in a 401(k) or 403(b) plan, you can contribute $19,750 per year, and if you are over 50, that increases to a total of $26,000 per year. For Traditional IRAs and Roth IRAs, you can contribute $6,000 per year per person, and if you are over age 50, that jumps to $7,000 per year. For IRAs, be careful, as there are phase-outs based on your adjusted gross income, which can affect how much you can contribute.

“One last tip, and something that is often overlooked, is to be sure that all of the beneficiary designations on your IRAs, 401(k) and 403(b) retirement accounts, as well as insurance policies, are current and up to date. Over the years, most people have accumulated several different IRA accounts from different employers or institutions and can’t recall who they’ve named as the beneficiary of these accounts. If you don’t recall who you designated, contact the investment company, your employer or your insurance agent, and ask for an updated beneficiary form.”

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Jay H. Levy of Measured Wealth Private Client Group LLC, and author of “Planning for Survival, The Great Retirement Conundrum.” measuredwealth.net

Are there general financial goals I should reach by the time I’m 40, 50, 60 if I plan to retire at 65?

Levy: “Listen, goals are nice to set but thinking about such things at the ages of 40 or 50 may be way too late in the process. In my book, ‘Planning for Survival, The Great Retirement Conundrum’ (Amazon and Audible), the premise is the reason the majority of Americans are woefully unprepared for retirement: They lack having been adequately educated in the area of financial literacy at an early age — somethjing that should start in their late teens or early twenties. For those that think this is just crying wolf, how do you explain statistics from the Federal Reserve in 2019 that an estimated 39% of Americans didn’t have $400 in savings. Or that other data points have even been more specific in approximating that as of 2018, 68% of people over age 65 didn’t have $1,500 in their checking or savings account. Not only are the majority of people not even remotely prepared to stop working and live 25-35 years afterwards, they do not even have six months of living expenses saved in an emergency fund.

“Those who wait to build financial goalposts in their 40s or 50s will have missed the value of a comprehensive plan which can assist in determining career choices (yes, financial considerations should be considered in job choices), where to live, getting married, having children or not (who actually calculates that the average child will cost somewhere between $265,000-$430,000 depending on geographic region — and that is without college costs), and other lifestyle considerations, will likely be traveling on a rocky road during their life.

Planning early will allow you to develop a flexible game plan that takes into consideration significant changes one experiences in life, such as taxes, estate planning, income sources, investment risk/reward strategies, health costs and so on.”

What’s the best way to estimate what I might need for medical costs or long-term care?

Levy: “I have been involved with Wentworth-Douglass Hospital (now owned by Mass. General Hospital) for over 15 years, including serving as past chair of the WDH Foundation Board of Directors. Healthcare costs have outpaced average inflation for decades and because of the aging wave of baby boomers coming into play, there is no reason to think that will be changing in the foreseeable future. Because of this, and the fact that Medicare is facing solvency issues, expect that the general public will be paying more into the system either through premium increases, higher deductibles and/or co-pays, more exclusions and higher payroll taxes supporting the program. Additionally, payouts to medical providers will likely continue to be reduced over time. Also, it’s unlikely that any other option such as a national single pay system won’t come without a significant cost through a change in the tax code for individuals and businesses. Remember, there really are no free lunches.”

How can your book help me prepare for an active lifestyle after retirement?

Levy: “My book, ‘Planning for Survival, The Great Retirement Conundrum,’ addresses both financial and the non-financial (holistic) considerations before you retire. I’m hopeful that people such as Jackie Eastwood (founder of Tissue Link A/K/A Salient Technologies and trustee of the New Hampshire College System) will continue to promote the book to the point where it can be distributed to every high schooler in New Hampshire as part of a financial literacy curriculum that is desperately needed. For everyone else who is beyond that age, I would welcome you to reach out to me at Jaylevyplanning@gmail.com or www.jaylevyplanning.net to request my interactive budgetary form and holistic selfquestionnaire, which will provide guidance in your decision-making process. I’m here to help.”

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Cathleen Toomey, vice president of marketing, The RiverWoods Group riverwoodsgroup.org

What are some of the things I should consider as I begin to downsize closer to retirement?

Toomey: “First of all, if you are considering downsizing in retirement, congratulations! Downsizing is very challenging, and it doesn’t get easier the older we get. At RiverWoods Exeter, Birch Hill and River-Woods Durham, we host several seminars each year to help people downsize. Too often, people decide that it is too hard, so they limit their lifestyle just to accommodate their stuff. When you consider downsizing, think long term — not just the next year or two, but what might you need 10 years from now. That will help you make a plan that accommodates changing needs, instead of requiring another move.”

Why should I move to a CCRC? I am totally independent. Toomey: “The curious case of CCRCs is that they are designed for active, independent adults, 62 years or better. When people ask me this question, often they don’t realize that CCRCs are insurance products, and in order to join, a person needs to financially and medically qualify. The medical qualifications vary from community to community, but basically, they all are designed to ensure that someone can live safely on their own. The goal is to move in to a CCRC when you are active, independent, and have the energy and interest to meet new people and engage in the huge variety of life activities there. Then, in time, if your needs change, and you need assisted living, memory care or nursing care, you can move within the community and get award-winning care at a fraction of the cost you would encounter if you were moving directly into a standalone assisted living or memory care community.”

If I plan to take advantage of a CCRC, when should I start that process, and what is involved?

Toomey: “Because the concept of a Continuing Care Retirement Community has become increasingly better understood, and therefore, more popular, it’s good to start the process of making a selection sooner than later, as many CCRCs can have long waitlists. During the time of Covid-19, there are often restrictions on visitors, which means you can schedule a virtual tour with an actual salesperson, anytime that fits your schedule. There’s no substitute for actually walking the campus, but you can get some great preliminary information about the community by participating in virtual events and tours.”

What are the different types of CCRCs, and how do I decide which one is right for me?

Toomey: “What many people don’t understand until they start their research, is that a CCRC, although it looks like a beautiful condo community, is actually an insurance product. Therefore, while the look and feel of the community, and the apartment and cottage choices are important, you should spend just as much time reviewing the contract and what it covers, as every contract differs significantly.

“There are three primary types of CCRC contracts: A, B and C. A detailed guide to understanding CCRC contracts is available to download on our website at riverwood-src.org/assets/2019/02/Insiders-Guide-Workbook.pdf “Type A offers the highest level of insurance, which generally means that if you transition from independent living to assisted living, memory care or nursing care, your monthly fee does not increase (except for two additional meals per day). Type B offers a defined level of insurance, which means that when you transition from independent living to assisted living, memory care, etc., your monthly fee goes up depending on your level of care. The increase is still priced well below market rate. Type C offers no guarantee of insurance, and is the least expensive option, but there is no discount on healthcare when needed.”