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Retirement is supposed to be the golden years of one’s life but when there isn’t a plan in place on how they will fund those years, it could lead to anxiety ridden times.
Today we’re going to break down some of the causes of these unintended feelings in addition to the framework we use to help our clients prepare for and accelerate through retirement as they build and execute on their bucket list items.
The Institute of Financial Wellness found that while 78% of retirees have bucket lists, only 23% make significant progress on them.
The rest? They get stuck in what we call the "Someday Cycle". That endless loop of "I'll do it next year" which stretches for years, and potentially never takes place.
So, what separates the 23% who live their dreams from the 77% who don't?
In our experience, it's not a money issue, it’s not a health issue, and it’s not even a time issue.
It’s a lack of both structure and building a defined plan with accountability mechanisms in place.
Think about it, for 30 to 40 years, your career and workplace brought some form of structure.
Deadlines created urgency, meetings created accountability, and paychecks created motivation.
Your days probably had shape, purpose, and direction. Then retirement hits, and suddenly, silence.
No one asking you for updates on your Italy trip. No deadline for learning a new language. No performance review measuring your national park visits.
And without external structure, we’ve seen even the biggest dreams start to feel optional.
One mechanism we like to discuss with our clients is called the Bridge System which is a method that builds a bridge between your current reality and your retirement dreams.
B is your budget alignment (not just having money, but knowing exactly what each dream costs)
R is realistic phasing (breaking big dreams into momentum-building steps)
I is intentional structure (creating accountability without the 9-to-5)
D is dynamic flexibility (adapting as life changes)
G is goal celebration (the psychology of progress)
E is emotional preparation (handling the transition that nobody talks about)
The key insight we try to convey with this system is when you budget for your dreams first, everything else adjusts around what matters most. When you budget without clarity, dreams can end up going by the wayside.
With that said, we also take into account that having the money is only half the battle.
The other part is something you don’t hear about too often.
For decades, you may have had conversations where someone asked "What do you do?" you had an answer.
A Teacher, an Engineer, a Doctor. Your job wasn't just how you made money—it was a part of your identity.
Then retirement hits, and suddenly that identity is gone.
This shift can leave retirees feeling lost, even when they have money and health.
The system we use addresses this with Identity Anchoring:
First is Values Excavation: What aspects of your work identity do you want to carry forward?
Next is Purpose Projection: Each bucket list item is assigned a “why” that connects to who you are.
Last is Story Building: You're not just retiring from something; you're retiring TO something.
An example of the emotional timeline might go something like this.
Months 1-3 is the Honeymoon phase where your newfound time and freedom can feel wonderful.
Months 4-8 is the Reality phase where you start to wonder, “Now What?”
And Months 9-12 tend to be an inflection point where some may face less desirable emotions and some might breakthrough to begin their journey and new purpose.
We like to start preparation for month 9 by starting before month 1.
The Final Word:
Now, of course, these are only general templates that we utilize with our clients when helping them plan for retirement. We want to convey that retirement is not only a shift in how you think about your finances, but it is also a psychological shift of how you will live out your life.
We always suggest working with your team of professional to help you build confidence towards your goals. Thanks for reading!
Disclaimer:
Rockline Wealth Management (RWM) is a registered investment adviser located in Islip Terrace, NY. RWM is registered with the U.S. Securities and Exchange Commission. Registration of an investment adviser does not imply any specific level of skill or training and does not constitute an endorsement of the firm by the Commission.
Rockline Wealth Management does not offer tax or legal services. The information in this material is not intended as tax or legal advice. Please consult legal or tax professionals for specific information regarding your individual situation.
All information presented is believed to be factual at the date of publication.
All investment strategies have the potential for profit or loss. Different types of investments involve varying degrees of risk, and there can be no assurance that any specific investment or strategy will be suitable or profitable for a client's investment portfolio.
Asset allocation and diversification do not ensure or guarantee better performance and cannot eliminate the risk of investment losses. The opinions expressed and material provided are for general information and should not be considered a solicitation of financial advice or for the purchase or sale of any security.
Real-life and fictional examples given in this blog should not be viewed as guaranteed outcomes when investing. Past performance is not indicative of future results and every individual’s investment circumstances are different. Individuals should consult their financial professional before implementing their investment plan.
Certain information contained herein constitutes “forward-looking statements,” which can be identified by the use of forward-looking terminology such as “may,” “will,” “should,” “expect,” “anticipate,” “project,” “estimate,” “intend,” “continue,” or “believe,” or the negatives thereof or other variations thereon or comparable terminology. Due to various risks and uncertainties, actual events, results or actual performance may differ materially from those reflected or contemplated in such forward-looking statements. Nothing contained herein may be relied upon as a guarantee, promise, assurance or a representation as to the future.