[Essay] A Major MILESTONE: I Quit My Job To Invest In Myself

📍Pensacola, Florida | Monday, October 26th, 2020I’ve been decorating my jean jacket with a memento from each place I visit. The gold, sequined Florida patch stands out the most which is fitting considering I’ve been chasing the Florida sunshine for…

📍Pensacola, Florida | Monday, October 26th, 2020

I’ve been decorating my jean jacket with a memento from each place I visit. The gold, sequined Florida patch stands out the most which is fitting considering I’ve been chasing the Florida sunshine for 2 weeks––the most I’ve stayed in one place since the beginning of September.

Giving My Notice

As of Monday, October 26th, 2020, I am jobless and homeless. 

For real. 

I have no job to run off to next; I’m just diving headfirst into an adventure.

I came to the conclusion that in order to fully enjoy my travels and give Daily Inspirato the attention it deserves, I need more time.

Time is a resource we all share. No one can stop it.

3 weeks for you is 3 weeks for me is 3 weeks for the next person.

I knew if I wanted to meet my goals, I had to take ownership of my full life and take back the 9-5, literally. Squeeze all the juice out of the lemon.

Ultimately, I’m electing to bank on me for a little while. To fully invest in me.

I had to take this inspiration, passion, emotion, and drive I have been feeling so immensely over the past few years and put it into something of my own.

Because if not now, when? 

 
Journal in the garden
A journal in a garden.

Decisions Take The Time They Require

It didn’t happen all at once. Speaking of time, the process of coming to this conclusion of leaving my job took some.

But it was time well spent because I wanted to be content in my decision and feel 0 regrets. 

In order to get to the place of tranquility, I needed months of internal and external dialogue to talk and write through the pros and cons, the “whys” behind what I’m doing. 

For me, commitment requires saying it aloud to trusted individuals. It requires recommitment, over and over again until it feels right.

My friends often remind me that decision making isn’t a one-off process. When I shared my news, they responded “you’ve been saying you’ve wanted to do this for years.” 

And they’re right. I have journal entries from when I was in Barcelona last year where I dreamed up the idea of traveling the U.S., seeking stories from inspiring women. 

Then, the idea felt far more “dream” than “reality,” yet 12 months later, I’m manifesting my destiny.

This is a reminder that though it may feel like decisions are made overnight, they’re actually the byproduct of months, if not years, of work, experience, and journaling. 

Decision making is growth, and growth takes time.

Following the daily 5 Minute Journal method has greatly helped me to focus and reflect on my progress, growth, and dreams. Learn more about the 5 Minute Journal practice here.

Following the daily 5 Minute Journal method has greatly helped me to focus and reflect on my progress, growth, and dreams. Learn more about the 5 Minute Journal practice here.

 

The Moment That Changed The Path Forever

A selfie taken moments before giving my notice.

A selfie taken moments before giving my notice.

Up to this point, and even now, I’ve felt the whole range of emotions –– from giddy to scared to happy to confident to energized to overwhelmed. 

When the time came to deliver my notice, I knew I was doing something I couldn’t take back. There was a finality in it that gave me a sense of strength because I was sure it was the right decision, but I also felt vulnerable since this process has resurfaced a graveyard of old scar tissue. 

Even after all the preparation, giving my notice was still shocking, but it was the shock to the system I needed. 

The excitement gave me the energy and focus to quickly pivot towards my new life. My mind began asking “what’s next in this new world?” “How are we going to structure time?” “What does success look like?” “How are we going to make money?”

… and I began to fill in the answers, one by one. 

Some challenges appeared impossible from afar (hello health insurance), but I’m pleasantly surprised at how skilled my mind and body are at responding as I’m in the middle of it. 

A big decision like this one is a life-changer, a divider, a bookmark. A moment I’ll recall on my deathbed. 

There will be “pre-US Clothing Confidence Tour” and “post-US Clothing Confidence tour” mile markers in my mind, and knowing that makes me feel reinvigorated.

 

But Why Leave The Steady Job That Let You Work Remotely?

Fair question, and one I knew you’d ask. Let’s dig into that scar tissue I mentioned earlier.

The reasons I want to leave a solid, predictable job in the middle of a [globally accepted] unpredictable year aren’t simple.

My decision came from a multitude of experiences, and some days it feels like one experience influenced this change more than the other.

(I am aware of the privilege I have to be able to make this decision).

 
Maddison and Travis on bikes
 

Reason 1: Travo 

For one, a huge inspiration for me to step away from my day job is my older brother, Travis. He passed away from the disease of depression at just 23-years-old. 

When the pandemic hit, I knew I was going to make a concerted effort to live,  particularly since there were moments early on where I heard the familiar question: “why are you even here?” lingering around in my thoughts. 

When the existential “why am I living?” question came back, I pulled myself together and actually looked at it.

I felt alert and on edge because I felt scared. These feelings and questions reminded me of the days in college where I wouldn’t get out of bed. When I would wallow around with this question in mind, in complete misery. 

Not to say there wasn’t any wallowing, but I do have more mental tools now, thank God. I was able to look at the question for what it was. And it was valid this time around. 

I did feel stagnant in my growth, both professionally and personally.

Above all, I felt stressed just like everyone else in the world. I had a narrow outlook with horse blinders up. I was alone in Maine when it was still cold, dreary, and gray. It felt option-less wherever I looked. I was scared I was going to lose my job, and it felt like every day was doomsday.

And then came Travis.

He started visiting me in my dreams.

There’s a particular, recurring dream where Travo and I treat Dallas as our playground. We spend the whole day roaming around, sometimes I’m filming him skating, sometimes we’re tooling around I-75 in his blue Hyundai, bumping a new mixtape. We play the music so loudly my ears ring from the subwoofers.

There’s usually a point in the dream where I know it’s not real because Travis had a million friends when he was alive and when we actually did hangout, someone was bound to call him up to take my place. 

But in the dream they never call, we spend the whole day together. Just us. 

I didn’t realize until recently that Travis acts as a caregiver in my dreams, calming me down when I feel most sick. So while I love his visits, they’re an indication that I need to change something in my life.

After a few of these dreams and my realization that his visits are due to enormous stress, I decided I wanted to live for myself, for Travis, and for my family.

That I needed to make this year count.

Because 3 weeks passed by, then a month, then a few more months … and I knew it wasn’t an option to remain stuck. It’d wallow again, and I didn’t want to go back to those days. 

To serve as a physical reminder, I had a ring made that lists a quote that means the world to me. It makes me think of Travis daily. 

“Leave with memories, not dreams”

It was a message to myself to stop planning and wishing and instead make it happen. Make a memory. 

And if not now, then when? When will I be able to explore life untethered?

 
To serve as a physical reminder, I had a ring made that lists a quote that means the world to me. It makes me think of Travis daily. “Leave with memories, not dreams” It was a message to myself to stop planning and wishing and instead make it happen…

To serve as a physical reminder, I had a ring made that lists a quote that means the world to me. It makes me think of Travis daily. “Leave with memories, not dreams” It was a message to myself to stop planning and wishing and instead make it happen. Make a memory.

 

Reason 2: Inspiration Is A Gift To Open Immediately

Another reason for opting for a bohemian lifestyle was due to the sudden, rather jarring, awareness of inspiration and what a gift it is. 

The bleak first part of this year made me conscious of this fact.

Inspiration is a renewable resource, but one that needs to be seized right when it’s felt. Excuse-free. Remove the roadblocks stopping you from taking advantage of it.

Why? Because even though it may not feel like it at the moment, the inspiration will leave, and it’s return date is unknown. 

Who knows when you’ll feel that fire again? 

With inspiration comes energy. The two are coupled because I believe it’s God’s way of saying seize this now [replace God with whatever higher power you believe in].

In a time when there was little to no inspiration (March 2020), I had to hold on to any little glimmer of hope I had.

It occurred to me that right now, at my age, I have too much energy to squander it. 

At the job I am now freshly safe from, I was told:

  • “Don’t take things so personally.”

  • “Only try as hard as you need to.”

  • “It’s just a job.”

I’d be told this at any company, I’m sure. I’ve heard friends remark similar grievances while working in different settings.

But my question is this: have these clichéd statements become so normalized that we accept them AND recite them to the incoming class of dreamers? 

The last one is the most disturbing. “It’s just a job”? So it’s just the 9 hours a day of my life? What does that even mean?

I’m 28. I have way too much energy and inspiration and passion RIGHT NOW to squander those feelings.

If I’m spending energy every day of the week focusing on a job that only wants a portion of my ideas, what am I doing? Am I really going to act like this inspiration and passion is going to be around forever? That’d be ignorant.

I know this energy and passion won’t be around forever and I need to seize the day.

 
 

Reason 3: Fulfillment Is the Reward For Risk

I am fantastic at avoiding pain. What can I do to set up for comfort?! 

But what I’m less skilled at is seeking pleasure at the expense of potential pain. 

If I really ask myself why I was scared to walk away from my job, it’s mostly security-based perks: health insurance/401k/paycheck.

The fear of losing those comforts far outweighs the potential growth earned from exploring another option, right?

Before I made this decision, I underestimated my ability to problem solve and design creative solutions in the absence of these security perks. 

Bottom line: I didn’t believe in myself, and certainly didn’t want to bank on myself.

 

A quote Brené Brown has tossed around so much I nearly attribute it to her is one by Teddy Rosevelt:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

-Theodore Roosevelt

 

I can say that I’m in the ring and I’m ok with the prospect of being marred by a bull any day if it means I’m pursuing my passions. 

If I’m living it. 

 
Me, realizing it was my last day of a traditional 9-5 (for now).

Me, realizing it was my last day of a traditional 9-5 (for now).

Building My Self Esteem, Accomplishing My Dreams

The growth earned from accomplishing my dreams is incalculable. 

A 401k/paycheck/health insurance is calculable. 

At the end of this journey, if nothing else, I will have accomplished my goals of:

  • Inspiring women to feel amazing about themselves in clothing and self-expression overall

  • Publishing a book

  • Traveling the U.S. while fully experiencing, connecting, and creating

It’s vulnerable to say I’m quitting a job because I am banking solely on myself. It’ll just be me, myself, and I (and my Digital Marketing Consulting company, INSIGHTIMIZE).

It feels like the pressure is on because if I fail, it’s no one else’s fault but my own. I am latching on to full-on accountability, and it’s exposing. 

But as with anything in life, the extreme feelings I’m experiencing are also producing equally elating ones. 

The feelings of freedom and self-trust are immense. I feel completely in my body and in tune with my emotions because they’re staring me back in the face, boldly. I can’t avoid them. 

 

I Am Glad to Breathe

Interestingly, subjecting myself to a little discomfort has made me want to live more. There’s some friction. There’s ignited passion. There's a reason. I am glad to be here.

I’m learning that saying “this is what I’m going to do, and here goes a big jump” is one of the biggest gifts I can give to myself. 

It makes for a bold life, an inspiring one.

And it feels right, given that I am asking other women to dig deep and explore their own selves, their consciousnesses, and to express themselves through clothing. 

I’m adding onto myself, too. I am feeling all of the feels, too. 

Here’s to chasing sunrises and sunsets in the months ahead 🥂🍾

 
📍Pensacola, Florida | Monday, October 26th, 2020

📍Pensacola, Florida | Monday, October 26th, 2020