I quit my job to chase my dreams. I almost gave up on myself in the process.

Delving into the details of your lowest points is difficult, but extremely cathartic. It's a level of vulnerability that I've been afraid to embrace for my entire life. Facades can be temporarily comforting. I instinctively hide behind them, even as I attempt to use my experiences to help others as a coach. A few months ago, I wrote about things that I learned during my transition into entrepreneurship, but I didn't fully express how difficult that transition was. The more I think about it, the more that feels like a disservice - to you as a reader, and to myself as I continue to learn from my experiences. With this story, I'm starting to fully embrace every detail of my journey - even the things that I was afraid to admit, before. I'm still a bit afraid, but am deciding to push through that. I hope that this story helps others who can relate to my fears, struggles, and failures.


Act I: Leaving My Day Job.

It could have been a regular monthly meeting with my boss. It wasn’t. I was putting in my two weeks notice, and I didn’t have another job lined up.

I listened to my boss drone on and on about our sales numbers and quarterly goals, but I didn't truly absorb any of her words. I was mentally preparing myself to leave the steady, stable job that had allowed me to move out of my parents' house about two years ago and embrace the independence that comes with true independence.

Well, my job had been stable when I was hired. In Summer 2014, I eagerly signed on to work as a full time territory manager for a prominent test prep company after months of struggling to make ends meet with temporary, seasonal work. In early 2016, my boss left the company. The time I spent under my new boss was a huge wake up call. That portion of my time in corporate America forcefully reminded me that playing it safe isn't always safe. 


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"My time in corporate America reminded me that playing it safe isn't always safe."


The test prep industry was losing relevance. Standardized testing was being given less attention in the college application process, and smaller local competitors started to eat away at more of our customer base. It didn't help that our new boss had little to no leadership experience. She had an Ivy League degree, but struggled to take charge and provide direction for the office on a daily basis.

I knew that the office was understaffed and struggling to make sales, but I felt completely blindsided when my boss brought me into her office for our monthly meeting and told me that I was at risk of being fired. I had been handling the workload of a three-man sales team by myself. Of course, that led to lower sales numbers. I didn't anticipate being singled out and penalized for a problem that I didn't have the ability to fix. I was informed that if I couldn't fix this office-wide problem within three months, I would likely be let go.

That was the day that I mentally checked out from my day job and decided to take control of the narrative. That was the day I knew it was time for a change. As my focus shifted, new opportunities opened up. I had been actively building my social media presence for years - primarily for my music discovery platform, Artistic Manifesto. However, as I matured and continued to find myself, I began to build connections based on the different facets of my personality - creative, focused, ambitious, sarcastic, humorous and Black. As I divested from my corporate career, I began to put the pieces together. I created a personal website to showcase all of the different creative projects I had manifested over the years. A creative resume.

When you put forth consistent, focused effort, you eventually attract opportunities that are suited for where you've been directing your energy. That's exactly what happened. About four weeks before I anticipated being fired, I got approached by a prominent Virginia-based creative firm about a music festival they wanted to pioneer. They told me that I'd be a great fit, given my reputation and what they could see about my accomplishments thus far. I felt validated. I felt like I was starting to see the fruits of my labor. I was excited for the opportunity. I took it.

Creating the music festival wouldn't be a full time job with benefits, but it would give me a decent amount of monthly income. I knew that I had interest in turning my success on social media into a business as well. Before moving forward with leaving my job, I designed curriculum for a social media coaching platform, and anticipated being able to use that platform to generate additional income.

I felt like I had a good plan in place, but the concept of leaving my job still felt a bit foreign and unfamiliar. That being said, I was determined to choose faith over fear. It was time to jump. Today was the day I would begin the process of taking matters into my own hands. 

The meeting was drawing to a close. My boss asked me, “anything else?” 

It was just about time for lunch, and I could tell she was ready to go. It was now or never.

I took a deep breath, looked my boss square in the face, and told her with a slightly trembling voice, “actually, I’m going to hand in my letter of resignation.” I felt liberated, terrified, relieved, and foolish at the same time as I handed her my freshly printed two weeks notice letter.

As I handed her that letter, a million thoughts flooded into my mind at once. I thought about the steady salary and healthcare I was leaving behind. I thought about how hard I had been working to plan an “escape route” from a job that didn’t value what I brought to the table. I thought about the children in D.C. and Virginia-based schools that I’d no longer be able to help once I left. Most importantly, I felt excited to move into work that better matches my God-given purpose. I had some exciting new opportunities in front of me, and I was finally taking matters into my own hands.

I didn't think it would be easy, but I knew I was making the right choice, though. Well, I thought I was.

Was I? Would everything be ok? I was about to find out.


My last day as an employee was July 15th, 2016.

I don’t like to talk about the period immediately following that day in my life. It was filled with sleepless nights, stressful days, unanticipated obstacles, and self-destructive mental chaos. I knew that the process of making it on my own terms would be a huge test, but I could have never truly prepared myself for the array of emotions that would ensue.

I left under the impression that I’d be working with the creative firm for an extended period of time, and that I'd be building my social media coaching business on the side.

That’s not even close to what happened.

 

Act II: Reality Strikes Back.

The months after I quit my job can best be described as a slow, inevitable spiral. Some days felt better than ever, but I couldn’t escape the gravity of my situation and its implications. That music festival I was working on? It never happened. In fact, I completely parted ways with the creative firm a few months after leaving my day job.

When I cut ties with that creative firm, I cut ties with my only consistent source of income at the time. I was disappointed in the outcome of that situation, but still determined to "make it" outside of the confines of a traditional 9 to 5. "You signed up for this," I reminded myself.

Close friends and mentors encouraged me at the beginning of my transition into entrepreneurship, but some people’s tones changed as the months dragged on and I was still struggling to figure things out. One conversation in particular almost took away the will that I had to keep going.

The conversation was with a close friend of mine. We have a lot of genuine chemistry as individuals and can identify with each other’s entrepreneurial struggles. We don't have to explain ourselves to each other often. Most things are simply understood intuitively. That being said, she’s a much more experienced and successful entrepreneur than I am, which made this conversation even more impactful.

It was a late night. I had endured a pretty exhausting day. You know those days where everything seems to go wrong? When a bunch of little problems turn into one giant mess? Yeah, that kind of day. We all have those days. I vented a bit, and spoke candidly about my growing frustration with my lack of coaching clientele, lack of income, and overall feelings of stagnation. 

I’ll never forget her response.

She spoke delicately, and slowly. She said, “you might not want to hear this right now, but I have to say it. You know I support you, and want the best for you, but sometimes we all need to sit back, reassess and figure out what's best. Maybe you’re just not meant to be an entrepreneur, Michell.”

I froze, but didn’t say anything, as she went on, to say, “and that’s ok. Everyone’s not meant to work on their own. It’s been four or five months since you quit though, Michell. If you had the mentality that it takes to succeed on your own, you would have been making money by now. You should have found a way by now. It doesn't get any easier from here on out."

That wasn’t the end of our conversation that night, but I don’t remember a single thing that was said from that point on. I was too busy trying to absorb what she had just said to listen to much of anything else. Her words echoed in my head for weeks after she said them.

“Maybe you’re just not meant to be an entrepreneur.”

“You should have found a way by now.”

“You should have found a way.”

Her perspective was honest and well-intentioned, but the words cut deeply during a moment when I desperately needed to find more confidence in myself. It hurt to hear a close friend who I looked up to tell me that I might not be cut out to be the man I thought I wanted to be. Sometimes reality hurts.

She apologized for being so blunt later on. I told her the truth: that there was no need to apologize, and that her opinion wasn't without merit. I appreciated her honesty, despite the way that her words weighed on me. Whether she was right about the solution or not, it was becoming clear that something needed to change.

If I had to pick one word to describe what I felt at this particular point, it would be “tired,” but I felt so much more than that.

I was sick of having to worry about how I’d pay for basic life expenses and agonizing over every single financial choice I had to make. I felt brave for taking the leap away from my safety net, but I felt more and more foolish as I continued to fall freely. I was embarrassed to be a 27 year old man who couldn’t adequately provide for himself. I was discouraged at the lack of results I saw from the hours and hours of work I was putting into my craft.

I was hesitant to accept that any of the progress I had made was worthwhile. I received a degree of accolades and media coverage during this period of time, but they felt hollow without accompanying financial benefit as I sought to create long term stability for myself. People told me I was doing great, but that was only through the extremely limited window I allowed them to see via social media and our conversations. I was angry at myself for not saving more money before making the jump.

I felt alone.

I grew distant from a good number of close friends, and lost a lot of friends altogether. I couldn't relate to as many people anymore, because of how radically my life had changed. I had more work to do everyday, and more financial constraints. There was no safety net, and no one to tell me what I should be doing outside of myself. I couldn't really go out as much, either.

When I did feel like I could feasibly take a night off and go out somewhere, I felt out of the loop and didn't even know who to reach out to. I would keep up a general facade of happiness and peacefulness on social media, but it didn't mean anything to me internally. For a few months, nothing felt right.

When I wasn't contemplating the specific act of quitting, I would only put in a fraction of the effort I was capable of giving, because I didn't have a clear picture in my head of where I was going anymore. Additionally, I didn't believe in the course of action that I was pursuing enough to put forth my best effort. I half heartedly labored through tasks that I told myself I should accomplish, with the faint hope that they would help me to get going in the right direction.

I felt helpless, and didn’t have any adequate words to express the depths of my helplessness to anyone. A few days after that, I had to prepare myself for another tough conversation. This time, I had to talk to my parents.


It could have been a regular conversation with my parents. It wasn't. I’m a 27 year old man now, but my father can give me certain looks that take me back to my childhood days when I was about to get a lecture for at least twenty minutes. It was a Tuesday evening. I was spending a few nights at my parents’ house to save money. Well, I had planned to spend a few nights, but those few nights had turned into a few weeks as I struggled to find the income I desperately needed to get back on my feet.

I sat at the kitchen table with my mother and father, waiting for them to speak. We had just finished drifting through meandering, meaningless conversation for about twenty minutes, delicately dancing around the pervasive elephant in the room. I had sensed that my father had something to get off his chest the minute he had walked into the house that evening. My instincts told me that I would be the recipient of his forthcoming monologue.

I was correct.

We locked eyes, and I no longer felt like a 27 year old man. I felt like a 16 year old kid who brought home a couple of C’s on his report card to parents who wanted straight A's.

My father asked, “how’s the coaching going?”

I didn’t have anything substantive to say. I hadn’t gotten any more clients than I had since the last time we had spoken candidly about my situation, and I knew what he was looking for: the bottom line.

I was failing at this whole "independent adult" thing.

He looked at me, and did his best to speak to me gently as he said, “Michell, your mother and I have spoken, and we think it’s time for you to start looking for a job again.”

I felt my stomach shift and my face flush as I did my best to keep a poker face and listen to my father. I began to space out, as the reality of my situation fully caught up with my thought process.

My father continued, “I’m proud of you for what you’ve done. But it’s not enough. You haven’t been fully financially independent for months. It’s time for you to step up and start focusing fully on the job hunt again. You can work on this business of yours in the evenings, or maybe before work, but it’s time to do what you have to do. I know you've got this millennial thing where you want to do things your way, but it's time to find a way that works. You've gotta do what you gotta do"

His face tensed up as he spoke. This conversation was as painful for him as it was for me. He didn't want to show it, but it was written all over his face.

Much like what my close friend had told me, this message was a hard pill to swallow, despite the fact that it was grounded in good intent and reality. In fact, it would have been much easier to swallow had I been able to hide behind the belief that my father was saying these things due to ill will, a skewed perspective, or wanting to see me fail.

I couldn’t hide behind either of those things. Instead, I simply sat and listened. Completely vulnerable. Defeated. Disappointed in myself. Wishing I knew exactly where I went wrong. Feeling like I had failed at accomplishing the things I wanted to accomplish the most.


I spent the next few days in a mental haze. I felt indecisive as I teetered between channeling energy into getting back on the job market or continuing to focus my efforts on making my true desires come to life. My self-belief was pushed to the absolute limit. I felt too panicked to take time for reflection, instead choosing to frantically bounce back and fort from task to task with minimal effect. When I finally forced myself to make time to reflect, I realized that I had to change my thought process before I could change anything else within my life.


Tweet:

"I had to change my thought process before I could change anything else within my life."


I started to think about the things that I had been able to accomplish up to that point. They weren't insignificant. In fact, I had accomplished a few things that I had dreamed of accomplishing for years. I had done a lot of worthwhile things since leaving my job, but I wasn’t actively being thankful for them. I realized that I had been making legitimate progress.The light at the end of the tunnel was still there. I just had to accept that it might be a bit further away than I'd like.

 


Act III: My Resolution

I couldn't afford to beat myself up anymore. It had been taking a toll on every single facet of my life. I didn't feel like the same person anymore. I needed to rediscover some degree of inner peace. External factors were unpredictable as ever. The least I could do was give myself a bit of inner stability. I went out and bought a white board. It was kind of on a whim. I hung it up on the wall next to my bed. I knew I wanted to be able to write things on my wall that would help me to think about myself, my situation, and my work in a better light.

I thought about trying to find an inspirational quote, but the ones I found didn't quite suffice. I wanted a quote that didn't make me feel inadequate, but still motivated me to make the most of every day. 

The external factors in my life give me more than enough opportunity to feel inadequate. I decided to write my own quote as one of my first acts of reminding myself that I am in fact good enough.

The quote reads:

"Never lose sight of the fact that the work you do today will help you to reach those big picture goals you've been dreaming about. Don't let temporary emotions stop you from doing that work today."

I've had this quote on my board for about a few months now. I see it every day when I get up, and every night before I go to sleep. Each time I see it, I say it out loud and reflect on the truth within both sentences.

It helps me to stop obsessively worrying about the big picture, and allows me to focus on the work that I need to do in my immediate future. At the same time, it also reminds me that this big picture dream that I have in my head is in fact very possible.

Reading this quote multiple times a day improved my general mood and outlook. Subsequently, it got me on track to operate more efficiently and proactively than I did in the past when I was busy beating myself up. I think it's earned a permanent place on my white board. When I made this change, I still couldn't see the results that I had been anxiously searching for, but I was able to deal with the tumultuous circumstances of my life more effectively.

That quote became my catalyst as I sought to continuously refine my daily habits. I was reminded more frequently that the little details of my day were important.

I started to wake up a bit earlier every day. I distanced myself from my cell phone when I started my work day so that I could tune out distractions and focus. I committed to organizing my thoughts every single day in a black notebook so that I could plan more thoroughly, and better track the things I needed to accomplish. I forced myself to go to bed earlier at night instead of staying up and wasting time on social media or tv. I was able to consistently maintain these standards by reminding myself of how much they would serve to cumulatively help me.

As the weeks progressed, the results started to match up with my mindset. The opportunities and income that I needed to succeed as an entrepreneur started to come to me. This didn't mean it was time to let up and celebrate my successes. Conversely, it meant that it was time to buckle down and focus on making the most of the opportunities that I had been waiting for.


Tweet:

"The work you do today will help you to reach those big picture goals you've been dreaming about."


Two months later:

It had been another long, but productive day. Those new habits I had been working to instill were paying off.

I was attracting new coaching clients every week, after struggling to find one client for months.

I was getting picked up for multiple brand campaigns through my agency, after waiting months to get my first one.

I was seeing my name as a byline in some of my favorite publications, after spending months wondering if I was good enough to write for them.

I looked back at the tasks that I had outlined for myself in my black notebook for the day, and decided that I had definitely exceeded the expectations I had set for my day. I also realized something important: I had actually made over $1000 that day, between checks for articles I had written, new coaching clients, and social content retainers.

A few months ago, I was making less than $1000 in a month. As I sat back and absorbed the changes in my life, my phone rang. It could have been a regular daily conversation with my mother. It wasn't. We were both coming to terms with the fact that my life was finally starting to change for the better, after months of wondering if it ever would. Our conversation felt lighter.

She didn’t ask me any questions about my job search, and I didn’t feel the need to give her any updates. I told her about my week, and about my $1000 day. It had already been a great 24 hour period for me, but hearing my mother’s words made everything feel just a little bit better, and just a little bit more real. I'll never forget her response.

“I’m proud of you for what you’re doing. It’s not always easy, but you’re making it happen. You’re doing it on your own terms. I have no doubts that you’re going to be successful. Just remember to keep thanking God. Remember who’s making it possible for you.”

We spoke for a few minutes, and then like most moms do after 10:30PM, she told me she was about to go to sleep. I hung up the phone, leaned back in my chair, stretched my arms out, and smiled.
 


Tweet:

"I quit my job to chase my dreams. I almost gave up on myself in the process."


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