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Quitting My Job: A One Year Check-in

May 15th 2019 marked one year since I walked into my boss’s office and announced that it was time to resign from my full time position. I held this position for 10 years and the change was indeed difficult. Today I’m writing about a one year reflection on quitting my job.

Quitting My Job: A One Year Check-In

I am sometimes awestruck in looking back to think about what that decision ultimately meant for my life. Though the decision ultimately came about after a year of thought and preparation, I actually had quite a bit of trepidation and fear.

Questions or rolling through my mind:

  • Will this work out?
  • Am I making a wrong decision?
  • Am I making the right decision?
  • What will the future hold?

Little did I know that in this move would be a great catalyst in many areas of my life.

The Short Backstory

In my former position as a Credit Manager at a commodity trading firm, I was involved in the world of high finance. Often times, I was called on to make decisions worth hundreds of thousands, and in some instances – millions of dollars – in a matter of seconds.

I was good at what I did and for the most part, enjoyed what I did on a daily basis.  I came into an environment that was in chaos, helped to clean it up and bring it to a point of stability.

However, I believe that two main factors played into my needing to make a career shift.

Quitting My Job: Why I Decided to Make a Career Shift

#1 – High Stress Levels

In this position, I was called to ‘always be on’.  I have a tag line where I told everyone I worked with that I was “24/7”, which was true. This meant I was available to anyone at the company, for any reason, 24 hours a day, 7 days a week.  

I had a company-paid phone and it was not uncommon to field calls while mowing the lawn at 6pm after work.  I was paid handsomely for this, but the trade off was in that I never completely let go of work. It was always with me, even when basking in the sun with friends after a long day.

Massive stress was the result.  It got to the point where I went to get an MRI as it felt as though something was wrong. The result? Everything checked out just fine; what I was feeling was the psychological effect of carrying too much elevated stress levels.  

I knew it was time to make a change.

#2 – Lack of Personal and Professional Growth

Another factor that lead to me quitting my job was lack of personal and professional growth.

When I first arrived at the company, I came into a challenging environment – exactly what I like as it pushes me to grow. Overall, things were in disarray – the company had just taken a large bad debt hit and needed big changes.  

Not only did I help to bring the company to a stable state, but I also developed a risk rating system and built in an IT infrastructure which allowed the company to better communicate across departments.  

By the time this project was completed, the department was on relative autopilot and I was left looking for more to do. The boss wanted me to be happy in managing the day-to-day elements, while I wanted to continue my personal and professional career growth.  

These two primary factors culminated into the moment that I announced my resignation. It was a year in the making – planning, preparing, deciding, and finally, executing.

Finally it was time to walk into my boss’s office and announce some of the scariest words in corporate lingo: “I quit”.  

Quitting My Job: Arrival Day

I’ll never forget that day – I had built up the courage to walk into my boss’s office to let him know that I was done.

I expected a full debate, anger, and disbelief on his end.  Volatile emotions seemed to be what I was in for, after all, this was only the second time in my life that I had to tell my boss that I was quitting my job.  

Rather than an uncomfortable situation, there was a cool calm collected conversation. My boss acknowledged that this happens, asked me when my last day was going to be and we began to lay out some initial work that I needed to do to roll things over.

It was all so easy, confusing, simple, and hard at the same time.  Why did I fear so much? Why did I have trepidation?

I knew that as soon as I had the conversation that the move had been right. Even though I knew the move had been right and that the situation was much less emotionally charged than I expected, I was in a bit of shock as how replaceable I was.  

Though I was someone who did a ton of work for the company, had great relationships with internal and external customers, and was an important piece of the fabric of the operations, I wasn’t so important that I couldn’t be replaced.  

The company didn’t come to a standstill on the day that I left.  In fact, it was business as usual. It was truly a humbling and eye-opening experience.  

In one year after quitting my job I have learned so much since that fateful day in May 2018.  Hopefully this post will prove interesting, raw, and open. I want to share what I have learned with you in case you find yourself in a similar situation.  

What are the lessons I have learned since quitting my job?

#1. The Grass Can Be Greener

One of the sayings that kept rolling through my mind as I struggling through making the transition to a new company or career path was, “the grass is not always greener.”   Meant to be a warning against taking things around oneself for granted, this became a self-sabotaging mantra that kept me locked into a position that was no longer serving me.  

I’d like to turn this saying on the head and state that “the grass is definitely greener”, at least when it comes to my situation.

It is an interesting element of our human nature that we desire safety and security. I personally found myself making all sorts of rationalizations for staying in a position that was no longer fulfilling me.

There was a negative thought process which kept me locked in to the role that I was at. Thoughts went through my mind such as:

  • What if I’m leaving a really great thing to seek something much worse?
  • What if this job is the best thing that I can get?
  • Am I deluding myself into thinking that the grass is greener?

After a year out on my own, I can firmly say that such negative-oriented thinking, though it helped keep me stable and rationale, is highly illogical. When it’s time to go, you know.  To ignore the prongs of self-actualization can only lead to inner turmoil and, in the end, massive regret.

I am now in a position where I am growing daily, enjoying the benefits of freelance work, and enjoying the majority of my days.  None of this could have happened had I not made the firm decision to leave my prior position. As I kept saying to myself throughout this process, “When one door closes, another door opens up.”  

#2. One Door Closes and Another Door Opens Up

A mantra that kept me going and gave me the motivation to resign from my position was the saying, “when one door closes, another door opens up”.

Repeating this to myself helped to remind me that should I choose to close the current door, something would definitely open up for me.  This saying proved itself to be completely and totally true.

I remember saying this over and over to myself as I was going through the challenging process of debating whether or not I should resign from my job.

Classic wisdom says that if you want to leave your job, one should always have another position lined up before parting ways with a current employer. While there is good wisdom here, I do not believe this is always the correct path to take.  

The current model for job hopping is pitched as when you find security, then you can leave security.  However, in my case that was challenging due to being in a situation that was zapping my daily energy.  Sometimes security for security just doesn’t make sense.

The position that I was in was draining my energy, came with high levels of daily stress and left me with feelings of de-motivation.  The end result was I found it very challenging to go out there in the job market and actively apply for new positions.

Combine all this with the fact that I wasn’t sure that I wanted to keep pursuing the career path in that was on, and what I found myself it was a perfect storm for staying in an apathetic state which I have come to identify as “The Uncomfortable Comfort”.

In the end, I did close one door, not knowing which door would open, but fully believing that a door would present itself. I was more than proved correct.

I’m now building websites, investing my own capital which was not available before leaving, and have been consulting at Red Wing Shoes for the past few months. I am there with other contract workers and we refer to ourselves as the “Dream team”.  

It has been a fantastic experience that would not have been possible without leaving my previous position on faith.  Sometimes you need to close one door to have another door open up.

#3. You Might Just Be Better Off

This was the biggest eye opener for me.  By leaving a situation that makes you unhappy, you might just be better off even if your security suffers for a little while.

Many people do not do this because they are afraid of leaving secure situation.  I get it – there are bills to pay, others to provide for, and no one likes to be ‘unemployed’.  But I would argue that staying in a situation that you know you must leave – as I did for many years – hinders your life progress and holds you back.

The truth is that while you might have security in your current position, you might just be better off by trying your hand in another position, company, or career path.  It does require a leap of faith to dive into the unknown, but from my own perspective, that is where the growth is.

I have found that for me, Growth = Life.  If I am in a space where I am stagnating, then I feel like I am dying.  

In looking back a year in from my position change, I am thrilled that I took the leap of faith to delve into the world of the unknown.  It took courage to walk in my bosses office and put in my two week notice, but doing so has put me on a path of radical self-improvement and self-actualization.

There is a comment that has stayed with me throughout this entire process. Many comments were typical – “Wow” “Good for you” “Good luck” as they maintain a look of disbelief.

One person simply said, “I wish I had the guts to do what you are doing”.

It was so sad to hear them in a position that they wanted to leave.  We only have one life, so why not take the chance? What decision are you putting off today?  It doesn’t necessarily have to be job or finance related. What decision – if you took the plunge into the forward path – would lead you into a place you have never been yet need to go?  

You might just find that it is the path you need to travel.  

#4. New Skills Await You

One of my biggest eye-opening experiences throughout this entire process is that if you stay with the company for many years, it can be a good situation from a benefits perspective.

However, for the modern-day worker in the 21st century, it can be very disadvantageous from an experience and skills perspective. While at my former company, I did gain a lot of great skills, especially in financial analysis and soft skills.   Coming into my consulting career, it is now apparent that I hurt myself by not being up-to-date on the newest programs and software.

Just a few months ago, I was discussing a position with 3M.  They liked my background and I was well suited for the duties.  There was one problem though – I did not know two particular programs that were utilized.  

It didn’t matter that I was an expert in my current systems and in fact, helped build functionality into those systems.  It all came down to that I missed out on learning pertinent programs that would’ve helped me in obtaining that position.

This is why Job Hopping is Good for Your Finances.

#5. Trust That Everything Will Work Out

I believe that one of the biggest things that holds people back from changing course, especially when it comes to a job situation, is the fact that they do not believe it will work out.

I do not blame individuals, as it is human nature to seek security and comfort.  Anytime we go against that mechanism, we are going against our evolutionary traits.  One can see why switching careers or companies, beginning a business, or leaving a tough situation would be difficult, if not impossible for some people.  

For most people, the formula goes: The Known > Unknown.  

People usually want to be in a place where they know what they are doing, where they have mastery, where there is very little in the way of surprises.   

In making my foray into the world of entrepreneurship and self-employment, I had to directly counteract this mentality. I had to have trust, hope, and faith that everything would work out.  I also had to begin learning skills and pursue avenues I had never thought of before.

While the journey is far from over, I have directly seen the Universe and my Higher Power providing for all of my needs.

I did enjoy a bit of time off after quitting my job.  This period away from the hustle and bustle of everything allowed me to engage in a deep reflect on where my career was heading and what direction I wanted to take it.

So what have I been doing with my time?

  • I traveled to Boston and Nashville, two cities that I had never visited.
  • I began investing my own capital into dividend paying stocks which recently surpassed the $4k/yr mark.  
  • MoneybyRamey.com began in full force.  I have written upwards of 70 posts, my very first book on the budgeting process, and coming soon – a book outlaying my dividend investing strategy.

This period away really allowed me to rest and relax and prep for what was next. Eventually, I landed my first consulting gig at Red Wing Shoe Company, which has been amazing to say the least.

Matt-Ramey-Red-Wing-Shoes
Me at the Big Boot


None of this would have been possible had I not said it was time to venture out of my comfort zone and into the realm of the unknown.

By trusting in my skills, capabilities, and most of all – in a Higher Power that guides and loves me – I was able to take the journey into the unknown.  

#6. Proper Planning is the Key

Contrary to what some individuals believed, I did not make the decision to leave my company in a casual or spontaneous manner. In fact, the decision to leave actually happened one year prior in May 2017.

It came about after a conversation with my boss in which he made it clear that he did not see much growth in my future.  He wanted me to serve one function only and did not see any promotion or upward trajectory in my career path.

Knowing this, and having a general frustration with the lack of career movement, I knew that the time would come.  Thus I began laying out my plan. I set a date in my mind for a year out- May 2018 – when I would walk into his office and announce my resignation.

I began the process of fixing up my home to sell, beginning to save enough capital that I didn’t need to work right away, and started looking at a few different positions.

Though an idea was to find another position and transition to that, I did not find one that intrigued me during that year long time period.  Even so, I knew that when May 2018 rolled around, I would be done. In actuality, I had to be done – it was time for me to move on.

It was through this proper planning and execution that I felt comfortable enough to walk into my boss’s office on that fateful May day, and announce my transition into the new career path.

In hindsight – if I had to do it over again, I would have made the decision to resign quicker.  Though I certainly didn’t want to rush anything, I knew for certain that it was time to move onward.

Though this might have been the case, it was only through planning and then executing that plan that I reached a place where I was ready and set to move forward.  

#7. Trust Your Intuition

Last but not least, one of the biggest learning points throughout this process was that I need to trust my intuition. There came a point when some years earlier, I knew that it was time for me to start seeking other positions.

It was an idea that I didn’t logically understand, but it was something that I felt in my heart; intuition was telling me to move forward.

No longer could I be in the position at hand, even if it did make ‘rational’ sense.  Rather I knew it was time to venture out take a risk and trust my intuition that it would all work out.  

Though there would be much to miss in the position – the prestige, the money/benefits, and most of all, the people I enjoyed working with – it was truly time to go.  Since making the change and resigning from my job, I have learned to get more in touch with my intuition and not to ignore it.

Currently in my own life, there are some situations that I’m facing in which what my intuition is telling me does not make logical sense, but I’m beginning more and more to trust where that intuition is taking me.

By undertaking this new mindset, I have continued to hone and develop my intuitive skills to the point where I find that I’m making great business and life decisions.  Life i truly beginning to take off to levels I had only dreamed of previously.

Had I stayed in my old position, I felt that the ignoring of my intuition would have led to it gradually deteriorating away, almost like a muscle or a skill that atrophies away if it does not get used in a while.

I’m happy that I made the re-connection to trusting and listening to what my gut instincts are telling me about what I need to do.  I’m excited to see where this type of mindset continues to take me from here on out.

Quitting My Job: Final Thoughts

Overall, there are many things that I miss about my old position. I enjoyed most of the people, I enjoyed the money and benefits, and I enjoyed the prestige.

But at the end of the day I was bored, unfulfilled, and knew that there was a better environment and situation out there for me.

Now here I am, one year in to my new journey, making a good money starting out my career as a consultant, enjoying the freedom of entrepreneurship, all while building toward my own personal Financial Freedom.

These are all elements I did not have in my previous position.  I also see that these new circumstances would not have been available had I not took the leap of faith and ventured outward.


Are you in a similar position? Have you made or are you thinking about making a switch? Comment below and let me know where you are at, what questions you might have, or anything you like to discuss!

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