7 Hidden Roadblocks That Could Derail Your Retirement Plan

by | Mar 13, 2025 | Uncategorized, DISC Training, Leadership

Retirement is one of those things that can feel so far away—until suddenly, it’s not. Some people put off thinking about it, assuming they have plenty of time to figure it out. Others focus only on the financial aspect, believing that as long as they save enough, everything will fall into place. But retirement isn’t just about the numbers in your bank account; it’s deeply intertwined with your preferences because it’s more about crafting a lifestyle that truly suits you — your needs, your dreams, and, yes, your personality.

Think about it: after years of working hard, this is the chapter of your life where you finally get to enjoy the rewards. But if your retirement plan doesn’t align with who you are at your core, you could find yourself feeling restless, unfulfilled, or even overwhelmed by choices you didn’t anticipate. That’s why planning early—and planning right—matters more than you might think.

And if you’ve been considering retirement for a while but feel unsure about how to tailor it to your personality and lifestyle, here’s where the DISC model comes in.

The Four Temperament (DISC) Model of Human Behaviour (which you can learn more about here)—categorizing people into Direct (D), Inspiring (I), Supportive (S), and Cautious (C) personas—offers powerful insights into how different personality styles approach retirement.

Each personality style faces unique challenges when it comes to planning for this next phase of life. Understanding your DISC profile — which you can uncover through a DISC assessment — can help and assist you navigate potential roadblocks and design a retirement plan that feels natural, fulfilling, and stress-free.

Let’s break down the seven common roadblocks that might be standing in the way of your ideal retirement—and how your DISC personality style influences how you tackle them.

1. Pride

Pride can be a major barrier to good retirement planning. Some people hesitate to ask for advice, believing they should be able to handle everything themselves. But retirement is a big transition, and input from experts, family, and even peers can make a significant difference. Letting go of pride allows for better decisions and smoother adjustments.

D (Direct):

High-D personalities might see asking for help as a sign of weakness. To overcome pride, they should recognize that seeking advice is strategic, not a defeat, and can lead to better retirement planning.

  • Mitigation: Engage in peer groups where sharing knowledge is seen as leadership.

I (Inspiring):

High-I personalities may feel they need to maintain an image of always having it together, avoiding discussions about struggles with retirement planning.

  • Mitigation: Reframe retirement planning as an exciting journey to share with others, using brainstorming sessions or group planning to stay engaged.

S (Supportive):

High-S personalities might avoid asking for help because they don’t want to burden others, even if they need guidance.

  • Mitigation: Seek out supportive and trusted advisors who naturally want to help, such as family members or close friends.

C (Cautious):

High-C personalities may believe they can research and figure everything out on their own, resisting input from financial planners or coaches.

  • Mitigation: Recognize that expertise from professionals can refine and validate their own research, ensuring a well-rounded plan.

2. Worry

two people worrying about retirement

Worry is a natural part of retirement planning, but for some, it becomes paralyzing. People worry about financial stability, losing their sense of purpose, or adjusting to a new routine. The fear of the unknown can keep them from making necessary decisions, leaving them unprepared when the time finally arrives.

For that reason, it’s essential to recognize that while some level of concern is healthy, excessive worry can lead to indecision or unnecessary stress. Instead of focusing on worst-case scenarios, it’s better to take proactive steps to ease these concerns.

D (Direct):

High-D personalities may worry about losing their sense of purpose and authority when they no longer have a job to lead.

  • Mitigation: Channel their leadership skills into advisory roles, board memberships, or personal projects that give them control and direction.

I (Inspiring):

High-I personalities can worry about their social status post-retirement.

  • Mitigation: Focus on social contributions or activities where their influence can still shine, perhaps mentoring or community leadership.

S (Supportive):

High-S personalities may worry about being disconnected from their usual support networks or daily routines.

  • Mitigation: Plan regular meetups or establish new community ties before retirement to maintain social connections.

C (Cautious):

High-C personalities might fixate on financial and logistical details, overanalyzing worst-case scenarios.

  • Mitigation: Create structured contingency plans so they feel secure about potential risks, reducing their tendency to overthink.

3. Discontent

a discontented retired person

Some retirees find themselves feeling dissatisfied with retirement, either because it didn’t turn out as expected or because they feel unfulfilled. While many dream of endless relaxation, the reality is that without purpose and structure, retirement can feel empty.

This is the reason why it’s crucial to create a plan that aligns with what truly makes you happy. Whether it’s staying productive, maintaining and building relationships (especially by design!), or continuing lifelong passions, having a meaningful retirement ensures long-term fulfillment.

D (Direct):

High-D personalities may feel discontent if they lose the sense of achievement they had in their careers.

  • Mitigation: Set personal goals—whether it’s fitness, business, or learning—to keep a sense of accomplishment alive.

I (Inspiring):

High-I personalities might struggle with boredom if retirement lacks excitement and variety.

  • Mitigation: Build a dynamic schedule filled with travel, hobbies, and new social engagements to stay energized.

S (Supportive):

High-S personalities might feel unsatisfied if their routine changes too drastically.

  • Mitigation: Plan for gradual changes in lifestyle or work, ensuring they maintain some consistency in their daily life.

C (Cautious):

High-C personalities might feel dissatisfied if retirement isn’t as structured or productive as their working years.

  • Mitigation: Create personal projects, like writing, research, or financial management, to maintain structure and purpose.

4. Going Your Own Way

Some people insist on handling everything on their own, ignoring valuable advice and missing out on collective wisdom. Retirement planning doesn’t have to be a solo mission—it can benefit from different perspectives, especially from those who have been through it before.

D (Direct):

Again, High-D personalities might prefer to go it alone, potentially missing out on collective wisdom.

  • Mitigation: Consider collaborative planning sessions or partnerships where they can still lead but benefit from others’ insights.

I (Inspiring):

High-I personalities may reject conventional retirement wisdom in favour of spontaneous decisions.

  • Mitigation: Balance spontaneity with structured financial planning to avoid future regrets.

S (Supportive):

High-S personalities might quietly follow their own way to avoid burdening others, even if they could use guidance.

  • Mitigation: Identify trusted people they feel comfortable discussing retirement with to make informed decisions.

C (Cautious):

High-C personalities may feel they can research their way to the perfect plan, resisting outside input.

  • Mitigation: Seek expert confirmation to refine and improve their plans rather than viewing advice as interference.

5. Laziness

Procrastination is one of the biggest pitfalls of retirement planning. Many people assume they’ll “get to it later” or that they’ll have plenty of time to figure things out when the time comes. But retirement planning isn’t something that can be thrown together overnight.

That’s exactly why small, consistent actions early on can prevent stress and uncertainty down the road.

D (Direct):

High-D personalities might delay planning if they feel too busy or assume they can “figure it out” quickly when needed.

 

a document and other things needed for retirement planning
  • Mitigation: Block out dedicated time for retirement strategy, treating it like an important business decision.

I (Inspiring):

High-I personalities might avoid planning because they prefer to live in the moment rather than think long-term.

  • Mitigation: Make planning fun by visualizing retirement goals and working towards exciting milestones.

S (Supportive):

High-S personalities might find that comfort can lead to procrastination in planning.

  • Mitigation: Set small, achievable goals for retirement planning to keep momentum without overwhelming change.

C (Cautious):

High-C personalities might delay decisions because they want every detail to be perfect.

  • Mitigation: Accept that some uncertainty is inevitable and make progress with the best available information.

6. Fear

Fear of retirement is more common than people realize. The transition can feel overwhelming—moving from a structured work life to an open-ended future. The fear of financial instability, loss of identity, or simply not knowing what to do next can make people hesitate.

The best way to handle this is by taking control of what can be planned to reduce uncertainty. The more clarity you have about the future, the less fear will hold you back.

D (Direct):

High-D personalities may fear losing control over their lifestyle and identity.

  • Mitigation: Take charge by setting clear personal goals and maintaining some leadership roles.

I (Inspiring):

High-I personalities might fear social isolation.

  • Mitigation: Build an engaging retirement lifestyle filled with group activities and community involvement.

S (Supportive):

High-S personalities may fear major life changes.

  • Mitigation: Gradually transition into retirement with part-time work or volunteer opportunities.

C (Cautious):

High-C personalities might fear the unknowns of retirement, leading to inaction.

  • Mitigation: Use their natural inclination towards detail to thoroughly analyze and plan for various scenarios, reducing fear through preparation.

7. Bucket List

a note with “bucket list” written on it

Many people enter retirement with a list of dreams—travel, hobbies, and new experiences. While this is exciting, the challenge is that not all bucket list items are financially or logistically sustainable in the long run.

For this reason, it’s crucial to integrate bucket list goals into a practical financial plan rather than treating them as separate desires. Finding balance ensures that retirement is both adventurous and secure.

D (Direct):

High-D personalities may push aggressively toward big goals without financial foresight.

  • Mitigation: Set realistic financial milestones to fund their adventures responsibly.

I (Inspiring):

High-I personalities might prioritize their bucket list over financial planning.

  • Mitigation: Integrate bucket list activities into the financial plan, ensuring both are addressed without compromising security.

S (Supportive):

High-S personalities may hesitate to pursue bucket list goals out of concern for others.

  • Mitigation: Plan experiences that also include loved ones to feel more comfortable spending on personal dreams.

C (Cautious):

High-C personalities might overanalyze costs and delay experiences.

  • Mitigation: Set a reasonable budget to enjoy life without unnecessary hesitation.

Closing Thoughts

Understanding your DISC personality style can significantly enhance your retirement planning by addressing personal behavioural patterns that might sabotage your future comfort. While saving money is important, retirement planning also involves shaping a lifestyle that suits your personality and brings lasting fulfillment. And when you recognize how your personality influences your decisions, you can create a plan that feels natural and rewarding.

Each style brings its strengths and challenges to the table, but with awareness and purposeful adjustments, these obstacles can be navigated effectively. The key is to work with your personality, not against it. By embracing what comes naturally to you while adapting where needed, you can create a retirement plan that not only works but also feels right.

Whether you’re a Direct, Inspiring, Supportive, or Cautious persona, tailoring your retirement strategy to your personality not only makes the process more enjoyable but also more successful. Plan with your personality in mind, and you’ll not just survive retirement but thrive in it.

Your retirement should reflect who you are, especially after spending years working hard and putting others first. Now, it’s time to focus on what truly matters to you. So, if you’re ready to take the next step, visit our website today, take a DISC personality assessment, and discover what your unique personality reveals about your ideal retirement plan.

JJ Brun, The Retired Spy

JJ Brun is a recognized global authority on human behaviour, communications, and relationship development who served for 20 years in the Canadian Forces in the field of Human Intelligence. JJ has dedicated his life and his business to training thousands of people in the principles of human behaviour and effective communication practices across cultures.

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