The Ultimate Guide to Choosing a Retirement Coach

Cyn, a retirement coach, talking to a client on a patio

You’re excitedly crossing the finish line and entering retirement. 


Woo hoo! It’s a party 🎉




Your retirement feels — lackluster. 


Procrastination, aimlessness, and lack of motivation set in.


What’s happening?


Unlike what society’s stereotypes tell you, transitioning out of your current working life is tough.


Not to worry, though — you’re certainly not alone. 


And more importantly, you can turn things around (and pretty quickly). 


Retirement is an amazing time for personal growth, new explorations, and fulfillment. Challenge is simply part of the process.


While it’s not for everyone’s budget, one of the most powerful answers lies in finding a retirement coach.


This blog post will cover everything you need to know about hiring a retirement life coach — from what to expect in a retirement coaching process to how to find the right coach for you. 


Let’s start with the definition of retirement coaching, so it’s clear.


What Is a Retirement Coach?

A retirement coach specializes in helping people transition into the post-career phase of their lives. 


And if they’re a comprehensive retirement coach, they’ll help you plan and achieve your ideal retirement lifestyle that goes well beyond the topic of your nest egg and how your financial planner assists you.


They’re a life coach who will help you clearly identify the life you want, create a personalized plan to achieve it, and provide specific guidance as you follow their steps and process.


While the expertise and process vary from coach to coach, having a retirement coach can be invaluable in helping you unlock your true possibilities and craft your best retirement life.


Let’s face it, retirement is a huge life transition — one that requires an entirely new identity shift and a different set of skills. So much so that there are even five emotional stages of retirement that most people experience (the first few being less than pleasant).


the 5 emotional stages of retirement are: pre-retirement phase, honeymoon phase, disenchantment phase, reorientation phase, and the stability phase


And if you think hiring a coach is superfluous, think again. 


Nowadays, you can find a coach for anything. And we mean everything — like these window cleaning coaches or even a pet nanny coach.


When it comes to hiring life coaches, there’s a growing demand that’s projected to only grow. In fact, in the US alone, the life coaching market was valued at $1.5 billion in 2022, with an expected compound annual growth rate (CAGR) of 4.85% through 2030. 


us life coaching market growth


Which makes sense when you consider the significant 70% success rate of life coaching — according to the International Coaching Federation’s recent study, 7 out of 10 people who use life coaching services report their goals are met or exceeded.  


While it might seem like a fad and like you’re perfectly capable of mastering your own dream retirement life, learning from expert mentors is one of the best (and quickest) ways to learn, grow and develop.


Studies show that coaching can help reduce procrastination and facilitate achieving your goals. 


On top of that, according to a comprehensive ICF global study, life coaching can also improve your self-esteem, relationships, communication skills, and overall wellness. 

positive reported impacts of life coaching


Speaking of life coaching benefits, let’s quickly call out some more. 

6 Benefits of Hiring a Retirement Coach

6 benefits of hiring a retirement coach

#1 Expertise

When it comes to hiring a life coach, expertise matters.


It’s not only helpful but critical that your coach is well-versed in a particular field and industry so they can provide more purposeful, tailored advice when guiding you. 


After all, specialized coaches can provide more focused advice tailored to their specific field of expertise. 


Think of it this way. If you were a vintage car collector looking for the best in the business, you wouldn’t want just any general mechanic. You’d want to go to someone who specializes exclusively in vintage cars.


The same idea applies to life coaching — you want someone with the right expertise and experience to get the most out of your retirement coaching process. 


The latest data shows 71,000 certified life coaches worldwide, with about 23,000 in the US.

number of coaches worldwide


There’s plenty to choose from, so it’s about finding the right expert to meet your specific needs.


#2 Clear Direction & Process

A retirement coach is a perfect ally to help you move in the right direction. 


Sometimes, when you’re too close to a situation, you can find yourself stuck in a loop of indecision and inaction. And a retirement coach can bring a unique — and clear — perspective to help you break out of the rut. 


By breaking down each stage of your retirement plan into achievable steps, they can also provide you with a clear process and timeline to follow. 


And an effective process is important to 78% of people seeking coaching services, according to the International Coaching Federation

an effective process is important to 78% of people seeking coaching services


Ultimately, a retirement coach will help you make sure you’re moving confidently and, more importantly, consistently towards your goals. Their goal should be to help you make lasting improvements and changes that last a (retirement) lifetime.  


#3 Clarity & Sense of Purpose

On the topic of goals, setting them is just the tip of the iceberg.


Transitioning into a successful retirement is about embracing a huge identity shift. Finding clarity and your new retirement purpose is a foundational part of discovering your new identity and role so that you can truly integrate your dream life.


And a retirement coach can help you get clear on your retirement purpose — which you need to create meaningful long-term goals.


The emphasis here being on meaningful.


A large study on the personal goals of older adults identified two types of goals: self-preservational and self-developmental.


  • Self-preservation — is associated with poor physical health, feeling burdened by difficulties, lack of meaning in life, dissatisfaction with life, and negative expectations for the future 
  • Self-development — interest in the well-being of others, and is associated with feelings of well-being in later life


Sometimes, you’re your own worst enemy. And out of fear or uncertainty, you might find yourself (unintentionally) setting goals that come out of the self-preservation mentality.


A retirement coach can help you find clarity on the goals that foster a self-development and growth mindset and those that, more importantly, align with your sense of purpose and fulfillment.


After all, finding clarity on your sense of purpose in retirement is the top priority.


#4 Improved Mental & Physical Health

Retirement brings with it a whole host of emotions. It’s the culmination of a successful career and the beginning of an exciting (and sometimes scary) new chapter in life. It’s natural to feel a sense of loss as you leave behind old roles, routines, and relationships. 


It’s a massive identity shift — and that can take a toll on your mental and physical well-being.


Retirement coaching offers a unique blend of psychological insight, practical advice, and emotional support. The goal is to help you channel your energy and efforts in a clear direction that’s right for you — helping you to cultivate a more optimistic outlook toward the future. 


And it builds confidence and resilience. Recent research has found that resilience isn’t static but fluctuates depending on a person’s current circumstances. 


In other words, with the right support system, you can develop a plan that gives you the emotional resources to manage any roadblocks.


For instance, Cyn’s retirement coaching program provides a 75% boost in health, 57% more energy, improved mood, and better relationships, to name just a few.

the impact that "rewire my retirement" has had on retirees who took the course

Plus, research has shown that life coaching improves health outcomes overall. 


So if the transition to retirement poses a challenge (or several), enlisting help from a retirement coach could very well be one of the best investments you make for both your mental and physical health. 


Not to mention the savings you’ll capture from simply being proactive with your overall health and well-being.


#5 Accountability & Consistency

Accountability partners are an invaluable asset in achieving any goal. According to research, they increase your chances of success by 65%. And that number rises to 95% if you include regular check-ins. 


Now imagine having a retirement coach whose main job is to help you find clarity, hold you accountable, and keep you on track to your dream life. These are among the many advantages of having a retirement coach: their commitment to your success and progress. 


Plus, with a proven process in place, your retirement coach will keep you consistently achieving your retirement goals. They’ll challenge you to think bigger and understand the process of creating a retirement lifestyle that works for you. 


But sometimes, to think bigger, you have to think small. 


As in, teeny-tiny. Like our micro-stepping strategy that helps you break down the scariest, most overwhelming retirement goals and choices into bite-sized, manageable tasks. 


stop procrastination by following the magic formula of micro-steps and mini-goals
Your secret weapon to achieving any goal.


By completing a single micro-step daily, you’re consistently in a focused motion, making progress and avoiding stagnation. 


The reason why micro-steps work so well is because they give you just enough of a consistent dopamine hit to keep going and end procrastination.


Whether it’s from a pro or if you’re holding yourself to it, achieving your dream retirement life requires clarity, consistency, and accountability.


#6 Personal Support & Encouragement

When you embark on a long journey like retirement, it helps to have an expert encouraging and cheering you along the way. 


A retirement coach provides more than just accountability — they offer the clarity, support, and encouragement needed to tackle the tough retirement transition.


Think of it as your own personal cheerleader who’s keen on the ins and outs of your life. Your retirement coach knows the inner workings of your goals and what it takes to achieve them. They also understand when you struggle, lose motivation or just need a break from it all. 


That’s why a retirement coach offers more than technical advice. They provide emotional support, motivation, and positive reinforcement for your specific efforts and thought patterns. 


And according to research, positive reinforcement is essential for success. It encourages better behavior, builds self-confidence, and helps you focus on reaching your goals. 


Do you think you’re a fit for hiring a retirement coach? Here are nine signs you need one.


9 Signs You Need a Retirement Coach

If you Google “planning for retirement,” most search results talk about the financial planning aspect of it.


Which is just a reflection of how most people actually think of retirement: as something that’s purely financial and transactional.


But a retirement coach takes the idea of retirement to an entirely different level — one that includes growth, exploration, and fulfillment.


After all, there’s more to life than money, right?


If you find yourself identifying with any of these signs below, it might be time to invest in a retirement coach:


9 signs you need a retirement coach


#1 Feeling Like Something’s Missing

There’s a subtle void humming in the background, one that you can’t quite put your finger on. It’s a feeling of unease, of something missing from life. 


You may even appear to be doing all the right things from the outside and “have nothing to complain about” — but you’re still not deeply satisfied.


And you’re not alone. One in five adults who retired in the last five years have admitted to finding it difficult. And many struggle with the so-called retirement syndrome.


A retirement coach will bring clarity to what’s missing and help you fill the void, and find the spark of inspiration to make you re-discover your “why.”


#2 Waffling Between “Retire” vs. “Not retire”

Retirement doesn’t just mean leaving behind your job — for many people, it also means leaving behind a (big) part of their identity. 


After decades of being a professional, it can be scary to enter the unknown — aka a retirement life with no clear steps toward your dream life. Having to shift your mindset and adapt to a new way of life is downright intimidating. 


And it can even lead to depression. A comprehensive study on depression among older men revealed an undeniable connection between their sense of worth acquired through work and their susceptibility to depression when they retire. 


If you find yourself waffling between retiring, resigning, or not retiring at all, that might be a sign you need guidance from someone who understands your unique situation. 


the benefits and disadvantages of retiring from your job


This way, you can set yourself up to retire to something meaningful and fulfilling. 


A knowledgeable retirement coach can help you explore the right path and create an ideal retirement lifestyle that works for you — and only you. 


#3 Feeling Unfocused (& All Over The Place)

If you’re a high-energy, high-achieving retiree, then you’re probably used to having a clear focus and lots of accolades and feedback in your life. But when it comes to retirement, the lack of structure can leave you feeling adrift.


Without the right structure and retirement routine in place to support your focus, you may find yourself flitting from one project or to-do list item to the next without making any real progress. 


Another common behavior is doing what you’re “supposed to” do or trying the popular “retiree” activities that other people suggest. 


Hint: The answers for clarity and focus will never come from the outside. Your true passions and purpose are lit up from the inside out — and fuel your intrinsic motivation.


If you’re feeling scatterbrained, it’s likely because you’re missing a “thought bouncer.”  A study demonstrates that if you selectively ignore information, your aptitude for remembering the essential input is drastically improved.


In other words, the key to focus is being able to identify what’s important and tune out the rest. And a retirement coach can help you create a plan that works for your specific life so you don’t waste away in boredom, aimlessness, or even guilt because you’re feeling useless in retirement


With the right directed focus, you’ll put energy into what matters most and make tangible progress toward achieving your goals (and receive accolades again). 


#4 Feeling Rudderless & Lacking Motivation

Procrastination is an all-too-common occurrence these days, yet many don’t realize its connection to your sense of purpose. And this goes beyond your to-do list or responsibilities and duties that you’re putting off. 


When procrastination rears its ugly head, so do mindless addictions — like scrolling through your social media feed for the umpteenth time or compulsively checking email.  


So much of procrastination is driven by the pull of the digital world; statistics show that the average older adult daily spends between four and five hours on screens.


And when it comes to watching television, the correlation is real — after the 35-44-year-old bracket, the older you get, the more TV you watch. Older adults watch more TV than any other age group by far, averaging nearly 5 hours per day for those over age 75.

time in hours spent watching tv weekly by age group


Note that these numbers used to be higher (as in 47 hours and 13 mins per week for older adults over 65) when other screens weren’t as readily available to steal your attention away. 


As with any addiction, these time-sucking behaviors act as a distraction from the underlying root cause of feeling lost, fatigued, and rudderless


More often than not, the culprit is lacking clarity — a clear identity, a clear vision, a clear plan, and a clear path. 


A retirement coach can help you uproot your culprits and come up with a retirement roadmap that energizes and motivates you, making sure that you don’t lose sight of what’s important in your life.


#5 Feeling Lazy (& Guilty About It)

Sometimes it can be hard to muster the ambition to get off the couch and make something of your many opportunities — even if you know it conceptually, the action often suffers when there’s a lack of clarity.


On top of that, going from a hectic daily routine to a more relaxed pace can make you feel guilty that you’re not doing “enough.” After all, your body and mind have been conditioned to keep up with a certain demanding pace for likely decades. 


While research shows that sleeping in and sitting around could send you to an early grave, the truth is, just because retirement gives you the freedom to pursue what you want doesn’t mean it comes easy. 


To get the right momentum going again — our answer is you first need clarity. 


Otherwise, you’re stuck in a loop of feeling totally unfocused (sign #3), ping-ponging between projects, and getting nowhere fast. The goal isn’t necessarily to fill every waking hour with activities — it’s about finding fulfillment through meaningful pursuits that make the most of your freedom.


By the way, if you want help finding clarity, use this Finding Clarity Workbook — it’s a great place to start. 


finding clarity in retirement workbook


All in all, the right guidance will help you discover and embrace a retirement lifestyle that feels fulfilling and free of guilt. 


#6 Relationships Are Suffering

Retirement isn’t just about getting your financial house in order; it’s also about finding ways to deepen your relationship with the people you care about and connect with new like-minded friends.


The transition to retirement often results in couples’ increased reliance on one another for social stimulation and emotional support — but navigating this new dynamic can be tricky.


What’s more, the extended family dynamic changes. It can be hard to find ways to stay connected when your life isn’t on the same schedule as those of your children and grandchildren. 


On the other hand, relationship struggles can be hard, and the feeling of loneliness and missing connection can be even harder. With more than a third of older adults feeling lonely, it’s critical to find ways to stay connected with your loved ones and even expand your social circle.


Every third American senior is lonely


It goes without saying that while it’s not as convenient, staying social as an older adult is massively important. It’s more than worth the effort to make new friends, deepen your social ties, and fight off loneliness.  


A retirement coach can help you identify strategies for staying close to family and friends, and making new connections, especially if it means stepping out of your typical comfort zone. 


From creative ideas for maintaining relationships to identifying social activities that bring joy, a retirement life coach can offer guidance and support as you adjust to the new dynamics and create better opportunities for yourself.


#7 Missing the Old Days

Parting with a job or career that you’ve dedicated so much of your life to can be difficult. You may find yourself hating retirement and missing the old days, longing for the sense of accomplishment and purpose that came along with it.


That’s not to say that feeling nostalgic is necessarily a bad thing. Research shows that feeling nostalgic can increase optimism about the future.


If you reframe your thinking and decide that retirement is a new beginning, you can uncover new ways to find meaning and passion in life with the right guidance. 


Whether it’s through volunteering, taking classes, or starting a business venture — there are countless options out there for retirees to explore. 


The only caveat — trial-and-error or “wingin’ it” likely won’t lead you to success. 


Your new identity and role in retirement need to align with your true passions and sense of purpose and belonging. And this is an internal growth process that requires active self-discovery by first going inward.


A retirement coach can help you identify activities that suit your skillset and align with your values and goals. This will help you focus your time and energy on pursuits that actually matter to you, setting yourself up for a successful and fulfilling retirement. 


No matter how you go about it, staying stuck yearning for your past years will likely lead to depression, which, sadly, more than 2 million Americans over age 65 suffer from some form of depression. 


May you embrace your innate desire to grow and become your best authentic self, especially in retirement.


#8 Want to Feel Accomplished & Contribute

Feeling accomplished is a state of mind we strive to achieve — during all life phases.


Retirement is the ultimate goal for many. And it can be an immensely satisfying milestone after a lifetime of hard work. 


But, to feel truly accomplished, retirement doesn’t just mean the sum of your efforts throughout your career. It’s also an opportunity to contribute to the world and share your unique gifts. 


A study examined what gives retirees meaning in post-career life. And the answers were so diverse that they didn’t come to a single conclusion. However, the one thing all participants had in common was the shared goal of discovering how to make their time more meaningful and fulfilling.


Whether taking on a new project, pursuing an area of interest, volunteering, or mentoring — contributing to the world in your own special way is a big key to finding true accomplishment and (retirement) life satisfaction. 


A retirement coach can help you utilize retirement as your catalyst to finding that sense of accomplishment and purpose, determine what activities will bring you joy and contentment, and realize the full potential of this new chapter by creating productive habits


You can also take our 10-question Retirement Purpose Quiz to help uncover your sense of purpose.


#9 Craving Adventure 

According to a recent survey, the average retiree gets bored within the first year of retirement


the average retiree gets bored one year into retirement


Of course, when you find clarity and have something purposeful to retire to that doesn’t have to be the case. 


With a good retirement plan in place (beyond finances), you can use this important life phase to explore new parts of the world and venture into experiences you’ve never had before. 


In fact, engaging in new experiences is a crucial component in keeping your brain healthy and your spirits high. From traveling to learning a new language, taking up a hobby, or starting a business, retirement can (and should) be the ultimate time for adventure.


A retirement coach can help you develop a clear plan that allows you to fully embrace this phase of life and take on the challenges, experiences, and opportunities that await you. 


More importantly, with their guidance, you can be sure to show up more authentically, make the most of your retirement years, and truly enjoy your unique journey. 


How to Find the Right Retirement Coach

Now that you know what makes up a great retirement coach and the benefits of working with one, it’s time to start your search for the perfect retirement coach.


#1 Determine What You Want & Need

Before you start your search, take some time to jot down exactly what you want and need out of a retirement coach.


Getting the results you want is, of course, a factor, and there’s also time to consider. 


For instance, most clients typically hire a life coach for 6-12 months. Which makes sense if you consider the fact that you want significant long-lasting life improvements. 


how many clients life coaches have and how long they typically stay


It’s also worth noting life coaches have an average of 9.5 clients. It’s best not to hire someone who’s overbooked, as it takes true dedication, time, and energy from your life coach to help you achieve long-term success. 


With these details outlined, it’ll be much easier to vocalize your expectations and narrow down your list of potential options, so you can find a coach who not only understands what you’re looking for with the right experience and expertise.


#2 Research Thoroughly

Take some time to read reviews, testimonials, and client stories, and ask around for referrals. The internet is full of great resources, so take advantage of the wealth of information available out there.


It’s worth finding out what type of retirement coaching process your potential coach offers and making sure their philosophy aligns with yours.


And, of course, you want to ensure it’s within your budget. 


The average hourly rate is $151 to 300 per session, with long-term clients averaging between $2,000 and $5,000 per month. Typically, the minimum number of sessions is between 3 and 6 months.


Some life coaches offer other services, like group sessions or a course — although, in a recent survey, most coaches prioritized offering 1-on-1 sessions over group sessions (which makes sense because it’s such a personal journey), and their course averaged $1,000. 

average life coaching hourly, monthly and course rates, and the minimum recommended life coaching time


Budget aside, though, it’s about finding someone who can deliver results. After all, that will save you tons on the backend — as in, by hiring a life coach, you can proactively take care of both your mental and physical well-being and avoid future medical and counseling bills. 


Once you’ve done all this research, you should be able to create a shortlist of potential candidates. 


Now it’s time for the next step: scheduling an initial consultation with each of them and getting to know them. 


#3 Have a Test Run

Before you commit to working with any retirement coach, ask if they offer a complimentary consultation or trial session.


This is your chance to get to know the coach and see if their style and approach are right for you.


Take advantage of this opportunity — it’ll save you time and money in the long run.


P.S. Cyn does offer a free Breakthrough Session — in just 45 minutes, you can clarify the foundation of your dream retirement and see if you’re a good fit for her coaching program.


Alternatively, you can often scope out their coaching style, content, and material on their websites. For instance, Cyn’s free workshop on How to Live a Purposeful Retirement Life is a great way to get to know her style and process.


#4 Pay Attention & Trust Your Gut 

Your retirement coach should be able to explain their approach in a way that makes sense to you and answer any questions you have.


So don’t be afraid to ask. It’s only natural for you to want to understand their process before committing to working with them.


And, most importantly, trust your gut. If you feel like the life coach isn’t a good fit for you, don’t be afraid to move on and find someone else.  


Your retirement years can be a time of sheer joy and exploration. And the right life coach can help make that dream a reality. So take your time, do your research, and find the perfect life coach for you.  

You’re Invited: Check Out Our Retirement Coaching Process

At Second Wind Movement, we understand retirement should be an adventure. One where you get to explore the things you’ve always been curious about and do more of what sets your soul on fire. 


And we provide you with the exact tools you need to achieve your innermost dreams.


Enter… Rewire My Retirement, our signature 3-month program.


the rewire my retirement life coaching program opened on a computer


What is “Rewire My Retirement”?

Rewire My Retirement is a step-by-step system that helps you find clarity and live out your passions and purpose. By the end of the program, you’ll have actively taken clear next steps to achieve them.


Because our mission is to help as many people as possible live their dream retirement life, there are a few tiers of the program, including a DIY online version and a fully-guided coaching program with Cyn personally. 


While her schedule is often booked, she does manage to make room for just a few new private coaching clients per month, where your process is even more tailored to your individual needs, values, and lifestyle.


Of course, the private coaching package is not for everyone, but in case you’re curious, you can book a free Breakthrough Session — where, in just 45 minutes, together you can clarify the foundation of your dream retirement and see if you’re a good fit for her coaching program.


In a nutshell, here’s what’s included in our signature program, Rewire My Retirement:


  • Fully Guided Learning Program With Exact Daily Micro-Steps
  • ​Private 1-on-1 Coaching With Cyn
  • ​Retirement Life Assessment
  • ​Goal Setting Review + Feedback (from Cyn personally)
  • Goal Achieving Toolkit
  • ​Morning Routine Roadmap + Templates
  • ​Exclusive Community


How Does “Rewire My Retirement” Work?

Over the span of a 3-month minimum, you spend months 1 & 2 finding clarity through a very specific process that delivers and surfaces your innermost desires. Then, you spend month 3 integrating a process that turns your clarity into your reality. 


rewire my retirement 12 week journey map with achievements


For coaching clients, Cyn meets every other week with you in one-on-one private coaching sessions throughout the program. In between sessions, you spend 25 minutes, preferably as part of your morning routine, submitting your daily exercise to her. 


Because she receives these submissions in the background, it makes your coaching sessions that much more productive. 


And because you’re setting up a daily cadence of magical micro-steps, you’re letting neuroplasticity do the work for you, unlocking specific clarity from your subconscious while layering in a consistent process (aka rewiring your brain to achieve only your dream life). 


This is all a very intentional and simple process. You just need to be open-minded and truly committed to your dream life. 


If this resonates with you, why not take advantage of our free Breakthrough Session


Take control of your future today and set the foundations for your ideal retirement – you deserve it.

What's Your Retirement Purpose?

These 10 questions can make all the difference
portrait of Cyn Meyer, founder of Second Wind Movement and a certified retirement life coach
Cyn Meyer 

Retirement Life Coach

As a certified retirement life coach since 2018, Cyn has helped thousands of older adults turn their retirement years into remarkable years full of growth, purpose, and passion. Through her signature program Rewire My Retirement, she helps people achieve their best life across the 5 Rings of Retirement, which covers topics Growth, Community, Health, Giving Back, and Finance.

Cyn combines specific life coaching tools, neuroscience, and her extensive background in marketing (spanning 17 years) to make a powerful impact with Second Wind Movement – an organization dedicated to providing educational resources and coaching for seniors.

With meticulous research, insight, and passion, Cyn’s mission is to usher in a new wave of positive experiences for generations of retirees.

portrait of Cyn Meyer, founder of Second Wind Movement and a certified retirement life coach

Cyn Meyer 

Retirement Life Coach

As a certified retirement life coach since 2018, Cyn has helped thousands of older adults turn their retirement years into remarkable years full of growth, purpose, and passion (beyond the stereotypical financial planning side of retirement). 

She combines specific life coaching tools, neuroscience, and her extensive background in marketing (spanning 17 years) to make a powerful impact with Second Wind Movement – an organization dedicated to providing educational resources and coaching for seniors.

With meticulous research, insight, and passion, Cyn’s mission is to usher in a new wave of positive experiences for generations of retirees.