Becoming a Strategic Quitter (and Being Good At It)

Are you living the best version of your life? 

I’m a great believer in spending your life in a way that makes you happiest. After all, as the popular saying goes…this is not your practice life!

This is it!

Your one and only chance to live your life on your own terms.

Something that really resonates with me is the idea that sometimes you have to be a quitter to get the life you ultimately want!

As a fee-only financial planner who is also a certified Life Planner, I’ve written before about living your best life according to your goals and values. A life that rings true for you.

Your best life is all about your aspirations. You can only meet the future you want by carefully setting up personal and financial goals and developing a plan of action that is tailor-made for you.

What is the difference between strategically quitting and quitting because you are giving up?

Subscribe to the Financial Residency PodcastLet’s look at the words.  

It’s all about the feeling and ideas behind the word “quitting”.

In our society “quitting” has long been a hallmark of perceived personal failure. It was believed that you were “throwing in the towel” or “giving up”. 

That you lacked the perseverance you needed to succeed.

This is where strategically quitting enters the picture.

The word “strategically” indicates that you have a plan of action. You are not just quitting with impulsive disregard to your future goals. 

What if strategically quitting is exactly what you need to do in order to succeed? When you finally realize what you are currently doing is causing more harm than good? 

I am talking about physical or mental damage to you (or your family). It could mean you realize you can’t reach your goals on your current trajectory! 

Remember Einstein’s definition of insanity?

Doing the same thing over and over again and expecting different results ~Albert Einstein

When you strategically quit something you are opening up room for something new and better. 

You create space for new solutions in order to build your ideal life!

Where Are These Life Draining Traps?

A more direct question might be: What is rubbing you the wrong way?

  • How are you feeling physically?
  • What is giving you energy or taking it away? 
  • Where are you feeling anxiety, excessive frustration or prolonged friction?

Life draining traps can be in any part of your life.  

Once you’ve identified an area that is causing you concern—take a deeper look to see what specifically about the situation is causing the friction. 

  • Is it your job? (what about your job?)
  • The commute, administration, company or hospital culture?

If you are paying attention to your thoughts, feelings, and intuition, you’ll quickly be able to pinpoint the problem areas in your life!

Fears That Control You

Now, to get the ball rolling in order to change your situation…take a hard look at your fears. It helps to identify them.

  • What will they (your mother, friend, neighbor) say?
  • What if I fail?

Do you fall into the trap of worrying about what other people will think or say?  This is social anxiety at it’s finest. The fear of being judged and found wanting. Something to keep in mind is if they care at all it will only be a nine-day wonder! 

Ask yourself: Is someone’s opinion of my actions more important than how I feel? More important than what I need? 

How to Master The Art of Setting Money GoalsThe answer will probably be no! 

The fear of failure is all too common. It is really a fear of embarrassment, humiliation and ultimately being shamed. 

With all that said, it’s important to get to the root of your fears and put them to rest so that you are able to move forward confidently!

You may need extra support through counseling or a life coach in order to step into the next phase of your plan.

Once you do that, you’ll realize your own internal validation is really all you need!

Change Is In The Air

Are you stuck?

Do you observe the people around you as being miserable? Yet, your friends and family continue to stay mired in their day-to-day grind?

Buckle up, if you want to create the life you’ve always envisioned. A life that will fulfill you!

As I stated above, it will require you to work on your fears. It will mean making some big, scary changes (some that might not make sense to other people).

You don’t know whether you will succeed or fail.

You don’t know whether your friends and family will support your new endeavor.

I went through this personally. After I decided that I wouldn’t work for another financial planner. I wanted to create my own business, one that incorporated the things I valued most. It was a huge decision to leave a six-figure job, in order to start my own business. I wasn’t making anything and I left without a contact list. I started from the bottom up!

The people around me reacted according to their own values and risk tolerance. The people around you will do the same.

However, I had to decide if I wanted to live a 1/7th life (one day out of seven of true happiness). 

Are you doing that?

Are you plowing through 40 hours a week in a miserable haze? 

Working for the weekend (which is really only Friday night and Saturday)–before starting to dread the next week on Sunday? Has retirement turned in to your greatest goal post?

Are you worried about what the Dr. Joneses are thinking and doing? Is there some peer pressure going on?’ve talked about them before, they might drive a fancy car, have a nice new house and take extravagant vacations. Do you feel like you need to measure your success against what you perceive theirs to be? 

The problem is you never know what is going on behind closed doors. You can’t imagine what their struggles might be. You can only see the facade. 

The same thing can happen with emotions. You have to live your life based on you. What excites you and makes you happy. 

It’s best to strategically quit worrying about other people and focus on yourself and the life you want.

It will be a life that you look back on and celebrate the risks you were brave enough to take (even if they don’t always work out as planned)!

Giving Up Or Getting On With The Real Deal 

Let me point out that some of the wealthiest and philanthropic people have quit some of their pretty big goals. 

They’ve even failed at some things. However, when they “failed” or “quit” they got back up, dusted off and got back into the game. It might have been a new game, but the point is they adjusted and kept moving forward.

They didn’t give up–they got on with a new and clearer view of their real deal.

We don’t think of them as a quitter, failure or someone who threw in the towel because they ultimately managed to succeed.

Who are some of these people who are good at strategically quitting? Let me name a few: Steve Jobs, Bill Gates and Mark Zuckerberg!

Are you surprised at hearing these “big” names? Some of them even quit Harvard!

They are able to make decisions about strategically quitting the situations that didn’t work for them. The came back with renewed purpose to work toward the life they imagined!

Your Ideal Life

How does your current life stack up against your ideal life?

Have you ever taken the time to picture how your ideal life will look? How it will feel, taste and smell?

I have my clients answer some questions about what an ideal day, week and year look like. In my experience sometimes my clients are very close to that life, and at other times they are far away from what they imagine. 

The comparison creates awareness between your current life, and the one you really yearn for, so that you can take on the challenge of strategically quitting what is not serving you and bridge the gap!

After all, why waste time on activities, and jobs that aren’t bringing you closer to what you want? 

Most people think that money is the goal. However, time is actually your most important resource. Why fritter your time and energy away?

That is why strategically quitting (without burning relationships or bridges) is smart!

Quitting…Strategic Or Otherwise Can Be Painful!

By now you know where some of your life draining traps are. 

You’ve pinpointed your worst fears, know what your best life looks like and you are ready to get on with the real deal. 

And you want to start strategically quitting things that aren’t working in your life.

What do you have in mind?

I’m sure the answer just popped into your head!

give yourself the freedom to fail with your financesSometimes with all the knowledge and introspection, you will still have a pain point. Change is like that. It’s uncomfortable. 

Intellectually you can list the reasons why you want to make the change, but you still lean toward clinging to the familiar. 

That’s right, leaving the life you know, even if it’s not the right fit and you know it, can cause you to feel a sense of trepidation!

It’s a place where most people get stuck marinading in their fear. They put off taking action to save themselves short-term pain. It’s the great divide between the areas you are used to and the unknown. 

That tactic can also stunt your growth and cause long-term turmoil (coulda, woulda, shoulda syndrome). 

So…just do it!

Moving Forward

Is there a right way to move forward after strategically quitting something that’s not working for you?

Define it!

Writing your dream down will help to clarify it. Write down the steps you want to take and start taking them one by one!

Forget hesitation!

There is no perfect time to move forward, no “right time”. There will always be one more thing that you need to complete. One more milestone that needs to pass before you think you can move ahead. Hesitating creates a cycle of fear and indecision. 


The things you focus on most tenaciously are more likely to materialize. Your belief in the future and positivity creates the actions that bring your dreams to fruition.

Keep your boundaries tight!

Is someone close to you an energy vampire? They’ll feed your doubt and strangle your excitement and positivity.Physician Wealth Services

Don’t let anyone rain on your parade. Choose who you surround yourself with on this journey. This is an area where strategically quitting a relationship might need to happen. 

Remove it!

Yes, I’m talking about strategically quitting anything that is holding you back. Take a hard look at your life and where you want it to be. You might have anything from habits to people that need to be phased out!

Here some things to keep in mind:

  • In the scope of human history, fear has been a protective mechanism (After preparing as much as you can feel the fear and do it anyway)
  • Research and rehearse (this may bring you a measure of comfort)
  • Following through on new things might feel awkward at first (don’t mistake this feeling as the first step to failure!)
  • Approach your learning curve with the mindset of it being a process
  • Learn from your setbacks

Then take the first step forward….and live happily ever after.

There you have it. From the figuring out what the life-draining traps are in your life, fears that control you, making changes and getting on with the real deal (because I know you will).

Through strategically quitting those things that aren’t working, you’ll be able to move forward into your ideal life!

I’d like to hear your story. What traps or fears have you overcome? What changes have you made in your life to get on with the new reality that you want to build?