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How to Decide When to Retire?

How to Decide When to Retire?

July 18, 2023

For most of us born after 1950, our largest financial goal is to stop working for money. We might not call it retirement, because it’s not a stopping of work when it works best. It’s a changing of work. The freedom to do what you LIKE and to do it in the WAY that you like is often the best definition of the “after-career” stage of American life.

How is your game plan to transition into not working for money going? When will you be ready? In a few years, or 5, or 10, or even 20?

The decision to make a formal retirement plan is a big one and it can be pretty daunting. Maybe you would like to talk about your situation with an experienced, well-trained, CERTIFIED FINANCIAL PLANNER™ professional and Behavioral Financial Advisor. Yes, I’m always a fiduciary, I’m a CFP®

 professional, a BFA™, and I work on a fee basis. Follow this LINK if you would like to find a time for us to talk.

Recently, I completed the Behavioral Financial Advisor certification program. I undertook this process because over my 20-plus years as a financial planner, I’ve seen first-hand how important behavior is to successful outcomes for financial plans. And a big part of that behavior is the choices a family makes.

Knowing how important it is to make GOOD choices and understanding how hard it can be to make GREAT choices, I was struck by a recent article I saw from Tony Robbins, an American author, coach, speaker, and philanthropist.

You have probably heard of Tony Robbins. You make like him and his work...  you might not. But I found this article very relevant to the process of effective financial planning for families.

Let me know what you think.

“It is in your moments of decision that your destiny is shaped.”

Every aspect of our lives, from our relationships to our careers, hinges on the choices we make. 

Decisions have the power to shape our destiny and propel us toward the life we desire. 

They also have the power to keep us stuck and prevent us from achieving our goals. 

And a lack of decision can leave us feeling stagnate, depleted, and leads to a complete loss of momentum. Sometimes we’re so scared we won’t make the right decision that we choose NO decision and let the fear of failure paralyze us from moving forward.

In short, it’s the quality of our decisions that determines the quality of our lives.

Think for a moment about the most important decisions you’ve made in your life. Perhaps it was a move, a career change, to start a new relationship, or to end one...

How did you make those decisions? 

Whenever I make a big decision, there are key principles I use to make them with confidence and clarity. And just like a muscle, you can grow your ability to make decisions so you’re consistently making progress. 

  1. All Decision Making Should Be Done in Writing

When you try to make decisions in your head you do something called looping.

Your brain gets stuck in a loop because you're trying to take something complex and look at it from every angle. You turn each viable option over, examining it thoroughly, your thoughts branching out into other possibilities, and eventually, you’re doing that x 10.

You need a visual. Decision-making requires the review of lots of information – and it can overload the brain.

In fact, it’s been proven that the more decisions a person has to make in their day to day, the more taxing and energy-depleted they become. 

Decision-making is an energy-intensive process. Honor it.

Take a moment to write out what you know about the decision you’re trying to make. 

Sometimes what feels complex in our own heads becomes vastly simplified on paper.

  1. Be Clear About What You Want

The foundation of exceptional decision-making lies in clarity. To make effective choices, you must first gain crystal-clear clarity about your goals, values, and priorities. 

What is your ultimate outcome?

What do you truly desire?  

Clarity is power.

When you know what you want (your outcome) and your why (your purpose) decision making becomes simplified. 

If you’re unclear about what you want and your why, things will seem murky. 

You may be influenced by outside forces that don’t have your best interests at heart.

Knowing your what and your why will act as your true north when it comes to making tough decisions. 

“When you have a clear vision, the path ahead becomes illuminated, making decisions more straightforward and purposeful.” 

  1. Decisions Are Made on Probability

No one has a crystal ball to tell them with 100% certainty they've made the right decision. 

It’s about taking inventory of the information available and making the best choice possible.

Leaders are decision-makers. And they step into their decisions without total certainty that it’s going to work out. 

This is what sets them apart from everyone else. They’re willing to take action when everyone else is paralyzed by uncertainty. 

This is what made General Norman Schwarzkopf a revered leader and mentor to me personally.

I remember talking to Schwarzkopf about mentors that have shaped our beliefs about life and decision-making. He spoke of one of the generals he had worked for before he was the “Stormin’ Norman” he’s fondly known as today. 

General Schwarzkopf recalled a situation in which the general was asked to make a decision that he had been stagnant about for almost 10 years. The general looked at them and he said, “The answer is obvious, gentlemen.” 

And then he gave them the answer. He said, “That’s our decision. Move on it.”

After they left, Schwarzkopf approached the general and said, “Permission to speak freely?” 

The seasoned general replied, “Certainly.” 

Schwarzkopf said, “General, I know you don’t have a clue what those guys were even talking about.”

The general smiled at him, and he said, “You’re right. I didn’t understand all of it.” And he said, “But you know what? This has been a decision that no one’s been willing to make for 10 years.” 

He went on to state:

“For 10 years they’ve talked about it, going back and forth. The best minds have been on it, and they can’t decide one way or the other, so you know what? We need to pick one and do it. So, I just did. 

Because I believe that now all the best people are going to go to work on it, and they’ll either make it work or they won’t. They’ll see it’s not working, and we’ll change directions, and we’ll do what’s right, but what’s happened right now is a logjam of nothingness.

Decisions are power, and I’m here to make them. That’s what I’m in this position for. 

That’s what I’m a leader for.”

The general did what no one else could do: he acted.

Often tough decisions are less about making the “right” choice and more about making the choice.

And my friends, despite what you might think, you can always pivot.

If you wait to have all the information, so will everyone else. 

If you make a decision that turns out to be wrong or not the best choice, you can change things. The important part is making a decision to start with. 

  1. All Decision Making Is a Clarification of What You Value

Lastly, each decision we make should point to our values. 

It can be a tough choice you’re making, but if it aligns with what matters most to you, you’re propelling yourself in the right direction.

And there’s nothing worse than making a decision based on FEAR, rather than what you feel is right in your heart. 

When faced with tough decisions, it's crucial to avoid the trap of limiting beliefs. 

I’m worried this won’t work out because...

I don’t want to try that because...

Expand your options and explore alternative paths. Seek out diverse perspectives, gather information, and challenge your assumptions. By broadening your horizons, you open the door to innovative solutions and unforeseen opportunities.

Decision-making doesn’t have to be agonizing. It can be an exciting way to align with what you desire most. And you can treat each new decision like an exercise, building your decision-making muscle. 

What’s a current decision, big or small, you can apply these principles to? 

Is there a decision you’re procrastinating on making because of the fear of failure that you could take action on today?

How can you apply your WANT and WHY to simplify a decision that feels complex?

I’ll leave you with this my friends; while the responsibility of choice can feel weighty, it is our true power to own our destiny and choose our course

We are the captains of our journey. What will you choose?

Follow this LINK to Tony Robbins’ LinkedIn article on this topic.

If Tony has you motivated to tackle some financial planning decisions, you want to talk about your situation. I would be honored to visit with you. As a fiduciary financial planner, I’m always an advocate for my clients. I love talking with new people. Reach out and we can have a get-acquainted visit. Just follow this LINK to find a time that works for you.

Yes, I am a CERTIFIED FINANCIAL PLANNER™ professional and Behavioral Financial Advisor. I’m always a fiduciary and I work on a fee basis. And yes, I’m still taking on a few great families to be part of my financial planning practice.

If this article has you thinking about your own circumstances, contact my office at I am always happy to meet with people who are working on their retirement plans. Dunncreek Advisors does not provide legal or tax advice, nor is this article intended to do so.