The Strategic Retirement Planning Roadmap

Pretend that retirement is a road trip and that you want to go to the West Coast from the Midwest. San Francisco sounds nice this time of year. You know the direction, and you drive your car straight toward it. Simply head west straight, you say to yourself; it’s so easy you can set the cruise and fall asleep and you’ll wake up at your destination. The autopilot will take care of the whole thing.

Something tells me you’re not going to end up in San Francisco.

Call it luck, call it fate, or just call it inefficient use of technology, but it isn’t possible to be that precise over that span of distance. There are too many factors, and there are far too many forks in the road for the cruise control to handle the journey. You’ll get lost; one degree difference and you’ll end up in a ditch perhaps, or maybe, with enough distance, hundreds of miles off course.

One thing’s for sure: you won’t get to where you want to go.

Planning for retirement involves years instead of miles, but the distance and its pitfalls are just as significant if not more. Without adequate planning, life and its milestones become the hills and the valleys that can derail a plotted path. Without care and paying attention to the tweaks and changes, the adjusted degrees in the course, you won’t end up in San Francisco (happily retired).

Successful and strategic retirement planning involves setting a course, sticking to it, and making the adjustments and corrections needed for the journey to end successfully. Just like making small adjustments with your steering wheel on a drive. It involves compiling a roadmap for your trip and using a guide to help chart your way. A good financial advisor, in this case, can be your guide on this road trip of life.

Retirement has historically been classed into three basic phases: an active early phase, a settled phase, and a phase where aging and its limitations begin to take their toll. Since the 1970s on, new phases have been created to better hone the process into discrete units that better describe the retirement experience. Inspired by the work of Elizabeth Kubler-Ross and the five stages of death, five stages of retirement have been proposed.

They are variably referred to as:

  • Pre-retirement/imagination/visualization phase – This is the course setting phase of retirement. You’re envisioning retirement and your life free of a workday. You might be in early preparation by working a job with a defined-contribution plan, such as a 401(k). You’ve begun the financial planning, and you’re brushing up on your hobbies and interests to best prepare to use your time, and your resources, the best. This is the stage of most interest to financial planners. It’s where we can help the most.
  • Anticipation – You’re only a few years away from genuine retirement. Your planning has gone well, and you’ll be able to actually make the transition to retirement. There is giddiness, but there can also be anxiety or doubt. This is a big change, and you’re now becoming fully aware of the difference it will make to your life.
  • Honeymoon/the day of retirement – You’ve made it happen. You’ve shaken hands, and you’ve said your farewell to work. All is great. It’s new, it’s fresh, and you’re excited. You feel liberated from prior constraints. This phase can last around one year.
  • Reorientation/reality – This can be a tough one. You start to understand how you structure your new days and your free time, and what it means for your identity to no longer work. Many people find that a core part of their selves was framed by their career and its accomplishments. Some people go back to work in this phase or start their own business.
  • Reconciliation/the next chapter – This is the final phase. It involves accepting what you’ve accomplished, understanding what you can do, and discovering a new kind of contentment hewed closely to reality. Many people strengthen social connections in this phase or take up new hobbies. Some simply enjoy the time for what it is, and cherish the hours.

Not everyone will go through the five stages of retirement. In the 1970s, a sociologist named Robert Atchley proposed six stages, more robust in their detail than the five generalized ones. The largest difference was highlighting how routine becomes such a focal point for the retirement path, much like acceptance in the Kubler-Ross model.

There are different levels and layers to the planning in each phase, and for each goal. Pre-retirement is by far the longest and most importance phase. It spans decades. There are multiple large financial life events in those years, ranging from marriages, college or other schooling, kids, home ownership and mortgages, to business and career changes. Many people start their own companies. Saving for retirement can often be secondary in the list of financial burdens the average individual undertakes. On top of that, you should be enjoying your life; these are prime years.

So how does one go about planning for retirement in the pre stage?

The groundwork for a retirement plan is a time horizon: your current age and your expected or desired retirement age. In general, the more time you have between your current age the date you plan to retire, the larger level of risk to investments you can withstand. Many people choose to invest in stocks, which are riskier investments due to inherent market volatility. You also need to be aware of maintaining purchasing power during retirement, through returns that outpace inflation.

The older you are, the more you should be focused on security and capital preservation and maintenance. Older age isn’t the time to be experimenting with risky financial ventures that might derail a retirement plan. Securities, such as bonds, won’t give you the same financial benefits and potential windfalls as stocks, but they are safer and provide more income stability that is also less prone to volatility. There is also a reduced concern from inflation.

Breaking up the comprehensive financial planning and retirement goals into discrete sections and components is an important factor for determining success. For instance, if someone wants to pay for college, purchase a house, and save for retirement, it helps greatly to not only segment those goals by financial investments, but by years, as well. When it comes to a deadline for retirement, years are a form of asset management that can be utilized fully.

Another key strategic aspect of retirement planning is determining budget needs. The most important factor here is to have realistic spending goals and charted patterns in your daily life so you can translate that to the post-retirement world without a career. This charted spending will help you determine the size and diversity of your retirement portfolio. It can’t be stated enough how important it is to be realistic about this; being caught with less money than you require for your standard of living can be a recipe for disaster.

If you’ve chosen the investment route for financial planning, calculating after-tax rate of returns and constantly tweaking risk tolerance will be a key strategic goal on your roadmap. Assessing risk tolerance and proper portfolio allocation can be daunting, as it involves numerous factors. This is a key area where a good financial advisor can step in and help tweak and manage your map. You want to be free to enjoy your retirement in as much financial security as possible, and financial advisors can do the grunt work to ensure you have less on your plate.

Many retirees also find estate planning to be a large mental and financial burden. It’s never easy to plan for end-of-life scenarios, but it’s crucial to make sure life insurance is in place and provides adequate coverage to avoid hardship for your loved ones following death. Ensuring portfolio investments are distributed properly and equitably to chosen beneficiaries can mean working with advisors and planners to assess risk and benefits. Planning for estate taxes and various costs is essential early on. Organizing and funding a trust is often a good strategy for early retirement and estate planning, especially when one has just started a family.

Retirement planning now falls on the individual more than at any other time in the past. Defined-benefit pension plans provided by an employer that guarantee a retirement income for an employee are becoming more scarce every year. Defined-contribution plans, or those handled by employees, such as the 401(k), are much more common and mean you’re on the hook for your own retirement outcome. Your best friend in this is going to be a flexible portfolio that can be adjusted not only to market conditions, but to your personal goals and needs. As your retirement objectives or trajectories change, so should your investments be able to adjust accordingly.

As you can see, the road to retirement is paved with many potential complex hazards. Financial advisors and planners exist to help guide your car on its journey to the right location. With subtle tweaks and course corrections, you can make it to where you want to go and also provide stable living for your beneficiaries. We help you not only pick investments that are right for you, but we also help you see the risks, benefits, and potential outcomes of any financial decisions for you and your family.

Financial planning involves working closely together to tailor a plan to your needs. Your current age, risk tolerance and your time horizon are factored in to lay the groundwork for a successful retirement plan. Strategic financial planning for retirement, like traveling to a location across the country, may not be able to be done entirely on autopilot, but with the right guide and tools at your disposal you can not only make it there, but thrive when you do.

Retirement is the age when you should enjoy yourself and make the most of the many years of hard work you put in to earn it. The most important thing is to cherish the journey of your life and understand your destination as part of that journey.

This educational, third-party article is provided as a courtesy by Craig Willeke, Financial Advisor with Eagle Strategies LLC, A registered Investment Adviser and a New York Life company. To learn more about the information or topics discussed, please contact me at

Neither Craig Willeke, WILLEKE FINANCIAL GROUP, LLC and its employees, Eagle Strategies LLC or any of their affiliates provide tax advice. Please consult your own tax professional regarding your situation.