5 Things I Wish I Knew Before Retiring – Trajan King

5 Things I Wish I Knew Before Retiring

It’s a hot topic, everyone wants to retire. Some want to go to the Bahamas, some wish to have a good time with their family, and some want to try their hands at something new. 

Retirement can be a wonderful time to relax and enjoy the fruits of your labor, but it can also be a challenging transition if you’re not prepared. I can tell you this because I wasn’t fully prepared when I retired 2 years ago. Like most people I thought retiring was gonna be fun and enjoyable and I was in for a shock…


There are tons of things that I wish I knew before retiring.  From financial planning to staying social, I’ll cover some key aspects of retirement that you won’t want to miss. Whether you’re just starting to think about retirement or you’re already retired, this video will provide valuable insights to help you make the most of your retirement years. So, sit back, relax, and let’s get started!


Retirement isn’t just about money

Surprised? Yes I was too… the first few weeks went great but soon I began to have this urge to go back to work, to meet my colleagues, to socialize. Retiring often leaves you with a lot of free time but not enough things to do…

In fact, many retirees find that they have more time, energy, and creativity than they had anticipated, and struggle to find purpose, meaning, and fulfillment in their retirement years.

For example, you may find that your identity and social network are tied to your career and workplace, and that you need to find new ways to connect with others and contribute to society. You may also discover that your interests and passions have evolved over time, and that you need to explore new hobbies, skills, and experiences to keep your mind and body active and engaged.

That’s what happened to me. I missed being around people, working on projects and engaging my mind. In fact, around 50% of people who retire early end up going back to work in some form, volunteering or starting new projects. Hardly anyone just sits on the beach and relaxes.

Imagine you’re like a family member of mine who managed around 200 people. He was the top dog, at the top of his game. He retired and next thing he knows he’s gardening all day. That’s a big change.

Your Financial Situation May Change

I retired with a decent amount of money in the bank account. I expected to receive a specific sum per month and while the first few months went well, the situation rapidly changed with coronavirus, the stock market crash, and the crypto meltdown. This taught me that it doesn’t matter how well you plan, things can go haywire without a warning. And I want you to be ready for a similar situation.

As Mike Tyson said, “Everyone has a plan until they get punched in the face.”

This means you may have to change your budget every now and then. You may even have to change some plans.

That trip to the Maldives may have to wait, your new car may get delayed…remember that retirement comes with uncertainty. 

Retirement is a process, not an event

Another common misconception about retirement is that it’s a one-time event that happens when you reach a certain age or milestone. However, retirement is actually a process that begins long before you stop working and continues throughout your retirement years. It’s something you’re always working on. This process involves both practical and psychological factors, such as your health, relationships, goals, and values.

For example, you may need to gradually reduce your work hours or responsibilities to transition into retirement, or you may need to seek new sources of income or support if your retirement savings are not sufficient. You may also need to adjust your expectations and priorities as you age, and adapt to changes in your physical, emotional, and cognitive abilities.

You may experience different stages and phases of retirement, such as the honeymoon phase, the disenchantment phase, the reorientation phase, and the retirement routine phase, each with its own opportunities and challenges.

For example, during the honeymoon phase, you may feel excited and liberated by your newfound freedom and flexibility, and enjoy exploring new hobbies, travel, or social activities. However, as the novelty wears off and the reality sets in, you may start to feel bored, restless, or unfulfilled, and wonder if retirement is all it’s cracked up to be.

I have a good friend who retired in his 30’s and for the first few years he spent most of his time sleeping in and playing video games. He looks back on that time now as time wasted. Not surprisingly, he’s now back working.

During the disenchantment phase, you may experience a sense of loss, disappointment, or frustration, as you realize that retirement is not a panacea for all your problems and needs, and that you still face limitations, risks, and trade-offs. However, this phase can also be a time of reflection, introspection, and growth, as you explore new values, goals, and possibilities, and seek new sources of meaning and purpose.

I was surprised how much I was still thinking about money and more importantly, about new things I could create. New projects. Which is what led me to create this channel. I got restless.

Also, part of my identity was that of a founder and someone who earned money.

During the reorientation phase, you may start to redefine your identity and role in retirement, and seek new ways to contribute to society and make a difference. This phase can also be a time of adjustment and adaptation, as you face new challenges and opportunities, such as health issues, family dynamics, or career transitions.

Finally, during the retirement routine phase, you may settle into a more predictable and stable routine, and enjoy the benefits of your hard work and planning. However, this phase can also be a time of decline and vulnerability, as you face the realities of aging, decline, and loss.

Most of all you need to continue to track your budget and look for ways to save. For example, I recently found out I could reduce my insurance cost by $1,300. I didn’t know that until I started looking into different options. I thought I was done thinking about money, but things still cost money 🙂

Retirement can be both rewarding and challenging

If you are thinking of retiring then know that retirement isn’t just fun and laughter, it can be full of challenges too, especially if you’re not prepared or aware of the potential  risks. 

Think about it.. As you grow older, you begin to face new challenges. You might be secure financially but you may end up facing health issues or social isolation that can affect your well-being and quality of life.

Don’t get me wrong here, retirement can be rewarding as well. It offers new opportunities for growth, learning, and fulfillment, such as travel, volunteering, or pursuing a long-time passion or dream. The key is to balance your expectations and goals with the realities and limitations of your retirement situation, and to seek support and advice when needed.

Start to think now what you want it to look like and what your backup plan is. I had a vision of what I wanted to do, but then everything changed when the markets tanked and I had to rethink it.


Retirement affects not just you, but also your loved ones

Retirement is not only about you, it is about everyone around you, including your partner, children, and grandchildren. It’s not just your life that changes, it’s theirs too. 

My wife and I talked a lot about what we expected.One of the best things we did was to have a finance meeting every Sunday night. We started when we were getting out of debt and continued throughout our journey. Few things can bring you together like communicating well about money (or tear you apart by not communicating). If you’re not on the same page, it can be difficult as I’ve seen in my own extended family. That’s why it’s so important to talk about it regularly and openly. You may not agree on everything, but talking about it is a huge step toward figuring it out.

A challenge we faced is that my wife planned to go to work when I retired. She was excited about it and when I wanted to go back to work, we had to figure out childcare and plan our time to also give here what she needed to feel fulfilled.

Don’t Wait for Retirement to Enjoy Life

I made a video about different types of retirement, including just taking time off for a few months (mini-retirement), changing careers, a sabbatical or moving to a different country. Life’s too short to wait. Make the most of the time you have now, whether you’re retired or not. You have a lot of options and retirement doesn’t mean hitting the beach at 67.

I’d say that you make a list of things to do before retirement such as visiting your favorite country or learning your favorite dance move because there are certain things you may not be able to do once you retire due to health concerns and other such issues. 

A lot of people believe that they’ll have all the time in the world once they retire, which may be true, but age or health may not always be on your side. You don’t want to feel pressured into doing things once you retire, retirement should make you feel lighter so don’t wait for retirement to enjoy life. Live some today.


These are the things to know and do before retirement. Retirement can be a lot of fun but it can also be challenging. Knowing what to expect can make the process easier.

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CFO & former Wall Street analyst helping your reach financial independence.

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Trajan King

Hey hey. I'm Trajan. I'm a minimalist entrepreneur who loves exploring the world (42 countries), learning new things (7 languages) and trying to get better every day (working on my backsquat).

I write about entrepreneurship and building an optimized and happy life through systems, good habits and scientific research.

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