The Longest Day of My Life

May 20th, 2013 – New York City.

“How much is this luggage?”

“It’s $199”.

“Oh. What’s the cheapest luggage you have? I just need a small handbag. I can’t afford this luggage.”

“This is the cheapest we have, Sir.”

Did you ever get to the point where you can’t look at your bank account because you’re afraid of what it’s going to tell you?

Have you ever added up your expenses in Microsoft Excel and couldn’t believe what the total was? I mean, literally not believe that the sum function in Excel was telling you the truth, so you added it by hand?

That was me.

The answer was the same regardless of how I added it up.

I was burning $10k / month in expenses, and I had no idea how this happened.

I didn’t do drugs. I didn’t party. I didn’t shop. I didn’t travel. I was reasonable with groceries. I had a mortgage and a wife that was more frugal than me.

How in the world did me living on my own means add up to $10k a month in expenses?

My expenses were higher than my income. I was losing money fast.

I flew to New York City to interview for a job I didn’t want. This job was was my backup plan.

While I was there, my luggage that I’ve had for a good 8 years fell apart 2 hours before my interview.

I was in the middle of New York City and was in a frantic mode to find new luggage. Luggage that I couldn’t afford.

I couldn’t come while holding my luggage in complete shambles. I would have been rejected before the first words came out of my mouth.

I made the last minute decision to buy new luggage. The new luggage that I definitely couldn’t afford. I had no choice. I couldn’t price comparison shop. I was running out of time.

I made a choice to not look at my bank account. I didn’t want to know the answer if I could afford this luggage or not.

18 months prior I made the decision to quit my full-time job. I was done with the rat race. I was done with the 9-5. I was done making money by the hour, even if it was considered “salary.” I knew I was capable of more. I needed to get out.

However, I couldn’t make it work financially being an entrepreneur without a stable source of income. My Plan A, B, and C failed. And most importantly, my cash reserves plummeted.

I had no choice but to get a salary job. I called it the “real world.” The world I was desperately trying to avoid. The real world is PLAN D.

And here I am fighting to get back into PLAN D.


The one smart thing I did when I quit my full-time job was to prepare for PLAN D.

Meaning, If I ever needed to get a full-time job I could make a few phone calls and explore my options. I did this by keeping in touch with previous co-workers. I did this by networking my ass off in Chicago. I took 250 coffee meetings in 400 days.

I learned new skills every day. Whether it was programming or marketing or writing, I made sure that I was ready to go.

“In case of emergency use this hammer to break open the glass.”

I built my own hammer.

Within a week of deciding that I needed to use my hammer to break the glass, I had 3 interviews lined up. Everything was going as planned.

All of them were in consulting. Nobody saw me as a marketer. Nobody saw me as a writer. Nobody saw me as a programmer.

They saw my previous 8 years of experience doing consulting. I was a consultant by their terms. That’s what I was good at in their eyes.

I had no time to tell them what my dream job was.

Income and stability are what I needed.

Fast forward a month, and all of the interviews are completed. Every meeting went well. I was 100% sure that I would get at least two offers, if not three.

Friday, May 24th, 2013. (Memorial Day Weekend)

I used the leverage of having 3 solid opportunities to let them all know that they needed to get back to me before Memorial Day. As luck would have it, I found all the answers on the Friday before Memorial Day.

The reality was that my financial situation was in bad shape and I needed income faster than they would ever know.

Then the first phone call came. I took a deep breath while watching my phone ring. “please let this be good news,” I thought to myself.


“Robbie. I would love to have you on. But, you’re a little too premature for what we need here. The team likes you, but let’s revisit in 6 months. We’ll have a much better idea of where you fit in at that time.”

In any typical situation, this was a positive outcome. The company isn’t ready for me, but they liked me. The door was still open.

But, not in my situation.

Anything that resulted in me not working the following week was a failure.


“Robbie. We’ve decided to put the position on hold. The team really likes you, but we need to feel out the market a little bit more. Can we revisit in the next 6-12 months?”



“Robbie. You’re too senior for this position. The team likes you, but unfortunately, it wouldn’t be a fit for us. When we have a more senior position open up, we’ll let you know”.

You know how I mentioned PLAN D? This final rejection was PLAN Z. I thought I had this job in the bag.

And here I am.

Jobless. Incomeless. Lost. Embarrassed.

I secretly wished they just told me that they didn’t like me. I wish the company said, “Robbie, you’re not qualified for this job.”

I would have felt better.

It was the longest weekend ever of my life. I needed to go back and look at my options again. I was determined.

The problem?

It’s Memorial Day Weekend.

Everyone is off Monday.

To 99.99% of the world, a holiday on a Monday is a great thing.

That meant spending time with family. BBQ’ing, laughing and volleyball.

For me, it meant one more day I couldn’t apply for jobs. It was one more day I couldn’t email my contacts asking for referrals. It was one more day of me contemplating what my next steps were.

The day I got rejected by 3 different companies on one day wasn’t the longest day of my life. It was that following Monday, Memorial Day.

It was the first day I felt truly hopeless. I had everything under control. I PLANNED for this day, so this would never happen.

And here I am again, in a situation I told myself I would never be in.

6 weeks later I run into a co-worker at an alumni event. I must have worked with him for less than 2 days. I’m surprised he recognized me.

He asked me what I’m up to and I said: “Just finished my last gig, exploring my options.”

He was in a hurry, but he said to contact him the next day. He has an opening.

2 weeks later I nailed the interview and got an offer.

Thus, putting an end to PLAN D.

The funny thing is that I’m back to Plan A.

Plan A never dies. It just takes a little longer than you want it.

For many of you, you know you want out of your 9-5. You know you are more capable than what you’re achieving now. Except, that you’ve been in PLAN D mode since the day you started your career.

Don’t let PLAN D get in the way of what you want to accomplish. Just keep it there in case your original plan fails.

Plan A all the way.

PS: Read the only resignation letter template you’ll ever need.