On quitting: part two

[Read parts 1 and 3 of this story]

I flew into Pittsburgh that week a broken man.

It was an odd combination of shame, relief, and fatigue, but the anxiety was gone. I actually felt better than I had felt in months since the burden of my secret unhappiness was lifted.

It was in these moments that I started to feel a new outlook taking root: one that would no longer allow me to subject myself to continued unhappiness ever again.

The week was clipping along at a nice pace, and it was made easier because (irrespective of my narrowly-avoided mental breakdown…) I was flying to Phoenix that weekend for LiftOff with Pam Slim and Charlie Gilkey.

I know, right?

I was close to my teammate Chris during this time, so I filled him in on the fact that I’d be taking a week or two off, the fact that I almost died, etc.

Chris was younger than me and relatively new to the company, but he was a rising star on the project and I had no doubts that he could hold down the fort in my absence.

The world’s most awkward conversation

My manager at the time was a tall, headstrong, middle eastern man. He was a no-nonsense guy with many years of experience in corporate IT consulting. Let’s call him Fahim.

Because that’s his name.

We scheduled some time to chat about what was going on, and we commandeered an empty conference room when the time came. I took a deep breath and tried to explain the high points of what I was experiencing, and how I felt like some time off might be best.

Fahim was nodded understandingly as I meandered through my thoughts. When it was his turn to speak, Fahim shared how many consultants had felt the way I was feeling at the time. He cautioned that some of them make the mistake of quitting on a whim and have to come crawling back for a job a few months later.

“I’d apply to work at Starbucks before I came crawling back to this misery,” I said to myself. It wasn’t a knock on Starbucks, either. I just hated what I did for a living.

As we were talking, the lights in the conference room went out. The door was closed, so it was pitch black. As I prepared to fumble towards the door, Fahim casually dismissed the situation and instructed me to continue talking.


So we pressed on. In complete darkness. Nothing awkward about that at all. Thankfully, the power came back shortly thereafter, and we were able to continue the train wreck under the fluorescent illumination of the conference room.

The agreement is that I would take two weeks off and keep everyone posted about what I intended to do after that.

My life as a traveling consultant was typically spent onsite (see: in a different city) four days per week, with me returning home (or at least going somewhere else for business or pleasure) on Thursday.

And as I mentioned, I was scheduled to attend LiftOff, so I departed for Phoenix instead of Atlanta that week.

LiftOff Retreat

This transformational experience of LiftOff deserves its own post, so I’ll just give you the highlights:

  • I’m still in touch with the folks I met during the retreat.
  • I can trace between $10K and $20K of revenue that came as a result of my attendance (specifically, business derived from projects I came across through other attendees).
  • When I look back at videos of myself at LiftOff (shattered emotionally, 30lbs. heavier, and a bit unsure of myself), I see a completely different person.
  • There wasn’t anything in particular that I took away from the experience that helped me, so much as gaining the support system of crazy people who were in my corner. That’s all I needed.
  • During LiftOff, I booked three new clients.
  • Less than a month later, two of the clients had bailed on account of money issues.
  • The third client had plenty of money, but not enough time to stick with the work we were doing, so I fired myself.
  • The plane ride home from LiftOff is when I decided that I was definitely going to quit.

The ramp up

Upon returning to Atlanta, I started dipping into my Paid Time Off (PTO) so I could get my head together, ramp up business, and generate enough revenue to kiss my job goodbye. I also calculated what my emergency fund looked like in the event that I needed to live off of the savings.

During this PTO, I was able to work from home without being bothered with project stuff, I had time to focus on my web design/dev work, and the stage was set to take off like a rocket.

How did it go you, you ask?

Not too well. As it turns out, I picked up a lot of bad habits over the years. The most sinister one — an issue that I have to be mindful of to this day — is sitting in front of the computer even when I’m not doing anything productive.

This is dangerous is because a full-time job and steady paycheck is not (generally) impacted by an intermittent lack of productivity. Self-employment, however, is completely tied to personal productivity.

As a matter of fact, I’ve found that success as a freelancer and entrepreneur is almost completely correlated with self-awareness and self-discipline. There is no separation of how you feel and how well you work.

I took on a few projects, but they languished. I had neither the motivation nor the discipline to knock them out like I needed to. I think it’s because I was still suckling from the corporate teet and not actually in danger of starving to death.

Not yet, anyway.

The drama

Throughout my time off, I had weekly contact with my manager, HR Representative, and Career Counselor. I let them know how things were going, kept them apprised of my timeline (when I thought I might be back working), etc.

Fahim and I made tentative plans to chat one day, and for whatever reason, neither of us picked up the phone or cared enough to reschedule.

I wasn’t too terribly interested in talking to him about the situation in the first place, so I let it ride. What happened the following week however, was completely unexpected.

I got a call from my HR Representative asking me if I had been looking for projects. Perplexed, I reminded her that I was still technically on the project in Pittsburgh, and that I was just taking some time off. She informed me that I was being rolled off the project.

As it turns out, Fahim took me not calling as me not wanting to be on the project anymore. Instead of confirming this with me, he mentioned it to the person responsible for staffing the project, and this set off a chain of events that I lacked the political influence (you don’t think success in Corporate America is about skills, do you?) to derail.


I felt like my career was being hijacked. My conversation with Fahim resulted in the obligatory apology and acknowledgement of him being a bit trigger-happy, but this was little consolation considering the implications of his actions.

Part of me was upset, and part of me didn’t care enough to do anything about the situation. What bothered me most is that being unstaffed meant that I’d need to start looking for another project much sooner than I had anticipated (or risk termination).

I wasn’t ready to be fired.

This is another reason my memories of Corporate America are not pleasant: there’s always an element of fear. Of not being in control of your destiny. Of external factors determining your course. Never again.

[Read parts 1 and 3 of this story]

Willie Jackson is a Diversity, Equity and Inclusion (DEI) Consultant & Facilitator with ReadySet, a boutique consulting firm based in the San Francisco Bay Area. He is a frequent writer and speaker on the topics of workplace equity, global diversity, and inclusive leadership. Connect on LinkedIn or get in touch.