Win the Lottery? Here’s the First Thing You Should Do
Any windfall can come with a sea of emotions and decisions. You need to clear your head, and then find the right help. A Certified Financial Transitionist (CeFT) may be just the ticket.


Often when someone is faced with large, life-changing events, they are not thinking clearly. Even if the event is a positive one, such as getting the job they always wanted or winning the lottery, they may be overwhelmed by the lifestyle change. We have all read about professional athletes who have made millions of dollars during their careers ending up homeless within five years of retiring. The immediate reaction is: How can that possibly happen? The answer is easy, if they aren’t emotionally prepared and schooled in the responsibility of handling such wealth.
Often it takes a professional to help a recipient of sudden money to come to grips, and process how their positive change of circumstance could impact their lifestyle.
Winning the lottery
Probably the most random way of becoming extraordinarily wealthy is by winning the lottery. You buy a lottery ticket for $2, go to bed worrying how you’re going to pay your rent or fund your child’s college tuition, and wake up a multimillionaire. There are innumerable issues to deal with: taxes, estate planning, investing, long-lost friends and relatives, new “friends” who generally want something, old buddies who treat you differently, guilt, anxiety and fear.

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
A Certified Financial Transitionist (CeFT) may be the liaison that a person who has a sudden positive change in circumstances needs. CeFTs are financial service professionals with training in dealing with the emotional side of money. They help the recipient integrate their newfound wealth into their lives, so they can reach their goals in a positive, non-destructive manner. A CeFT doesn’t tell the client what to do, but rather is their “thinking partner” to help explore options and come up with a plan.
A typical lottery situation
Joe comes from a working-class family. He tends to live from paycheck to paycheck. He generally takes his wife out to dinner for her birthday and their anniversary, but typically they have pizza or Chinese takeout with friends on a Saturday night. Joe’s car is seven years old, his home is well cared for but not fancy. His clothes are not new or fashionable. His wife, Sue, works part time but likes to be home when the children come home from school. Joe likes to buy a lottery ticket or two, but only when the prize is huge. On his way home from work Joe heard the Mega Millions was up to $370,000,000, so he stopped by his favorite corner store and bought a ticket. He put it in his pocket, went home, forgot to tell Sue about his purchase, ate dinner and went to bed. The next morning he heard that not only was there a winner but the ticket was bought in “his” store. He was nonchalant when he fished the ticket from his pocket, but as he checked the numbers in the newspaper, he practically fainted.
After Joe showed Sue the matching numbers they stared at each other in shock. All of the “if I ever won the lottery scenarios” went floating through their minds, but as they sat there the most pervasive emotion was anxiety laced with fear. They never needed a fancy estate plan – just a simple “I love you” will; taxes were taken out of their paychecks, and they didn’t have any investments so their accounting needs were minimal. All of their friends were in similar circumstances. Who could help them? Who could be trusted? They went on an Internet search and ultimately came to the Sudden Money Institute. They called SMI and got the name of a reputable CeFT.
Handling the winning ticket
Joe and Sue were petrified when they arrived at CeFT Jane’s office. Jane explained that although having great wealth most likely would change their physical environment, it didn’t need to change who they were. Jane explained that her job was to guide them through the process – to work with them about the feelings the newfound money created. They needed to have a game plan on issues of how they would handle requests for money from family and friends, if they chose not to work what would they do all day, where did they want to live, how to help the children to adjust. Jane explained part of her role was to help them come to comfortable decisions on these issues.
In addition to the emotional issues, she would help them set up a team consisting of estate-planning attorneys, a CFP who would assist them with their financial planning and investment needs, and any other specialists that they required. The goal of the team was to determine the best way to help Joe and Sue achieve their goals and educate them about their choices while, among other things, taking into account taxes, setting up trusts for their minor children, helping them decide if and how to be generous to friends and families.
Although this scenario focused on winning the lottery, the same principles apply to all large influxes of cash, i.e., inheritances, divorce settlements, exercising large option positions and selling restricted stock units or a business.
Large cash windfall do’s and don’ts:
- Take your time to become mentally and emotionally comfortable with your change of circumstance.
- Don’t make any hasty decisions or promises.
- Surround yourself with a team of professionals including:
Tax attorney
Estate-planning attorney
Certified Public Accountant (CPA)
Certified Financial Planner (CFP)
Certified Financial Transitionist (CeFT) - Make a game plan that gives you structure on how to proceed, including:
Make a budget and keep to it.
Decide who and under what circumstances you may/may not financially help friends and relatives.
Don’t be afraid to say no. - Remember you rule the money. The money does not rule you. It should not dictate what you do. It only allows you the opportunity to do what you want to do with it.
Disclaimer
Securities and Advisory Services offered through Cadaret, Grant & Co., Inc., a Registered Investment Adviser and Member FINRA/SIPC. HMS Financial Group and Cadaret, Grant & Co., Inc. are separate entities.
Get Kiplinger Today newsletter — free
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Barbara Shapiro is the President of HMS Financial Group located in Dedham, Mass. She is a CFP®, Certified Divorce Financial Analyst and a Financial Transitionist®. She is also co-author of "He Said: She Said: A Practical Guide to Finance and Money During Divorce." Her firm specializes in comprehensive financial planning with a subspecialty in divorce that assists clients' transition from marriage to independence with peace of mind and confidence. Learn more at HMS-Financial.com.
-
Five Medicare Changes Coming in 2026
Learn about the benefits that become permanent features of Medicare in 2026 and how they have been changed or updated since their inception.
-
Discover Which Five States Have AAA Offices Offering Real ID Services. Learn What You Need To Do To Take Advantage of Them.
A trip to the DMV can be a painful experience. Skip the line and visit your AAA office to get your REAL ID (select states only).
-
Four Tips for Mastering a Financial Security Mindset
This financial professional's mom helped him learn that financial security is more than making money — it's about cultivating a mindset that will help you stick to an investment plan even when times get tough.
-
Lessons to Be Learned From a $1 Billion Divorce
An estate planning attorney notes that an oil executive’s billion-dollar divorce could have turned out very differently if the couple had a premarital agreement and the executive had used asset protection trusts.
-
Four Ways to Use Your Tax Return as a Financial Planning Tool
Rather than filing away your paperwork and forgetting about it, this CPA recommends using it as a source of insight to optimize your long-term financial strategy.
-
How Women Can Turn a Gray Divorce Into a Financial Win
Getting divorced later in life can be a big financial blow, especially for women. But, as this financial adviser points out, it can also serve as a positive turning point for growth and independence.
-
Private Markets: Six Things Investors Can Learn From BlackRock's CEO
BlackRock's chief executive, Larry Fink, recently argued the case for increased access to private markets. Here's how a financial professional sees Fink's views translating into action for accredited investors.
-
I Found Out What It Takes for a Family Business to Thrive
A handy book and my chat with the chairman of Community Coffee offer some guidance on making your family business a success.
-
The Future of Opportunity Zones: Outlook for 2025 and Beyond
There are three potential paths forward for this innovative tax incentive program that's set to expire in 2026.
-
How Private Equity in Your Portfolio Could Boost Returns
And reduce volatility. A few decades ago, private equity was considered a 'cottage industry.' Now, it is a multitrillion-dollar asset class.