Why I Told My Boss I was Thinking About Quitting. (And maybe you should too) SEE VIDEO

The night before I was fired from my first job my boss asked me to stay late to finish up some bullshit paperwork that was definitely not time sensitive. 

I couldn’t understand why he was pushing it, but the next day I got my clarity.

My boss wanted me to stay late so he wouldn’t have to complete the tedious task…because he had planned to fire me the next morning.
The termination was perfectly timed to be on a random Wednesday on the last day of the month so I wouldn’t receive health insurance for the following month, thus reducing their costs. No severance was granted and I was immediately escorted from the premises.

I was happy to be rid of the company who would gossip about me in the next room, who would scold me for parking in a different parking spot every day, and who told me they learned the sound of my footsteps so they would know where I was in the office at all times.
Sounds horrible, right? And it was.

But my experience isn’t an anomaly. Many people have had the experience of being mistreated, taken for granted, or let go in a way that leaves us feeling hurt and well…less human. 

It’s no surprise then that when it comes time for us to leave a company based on our own free will, we get a little skittish about speaking up about it.
Nobody wants to risk expressing their unhappiness and finding themselves without a job altogether. However, the shadiness comes at a cost.
The cost of being weird about quitting
After my horrible departure, I ended up at a company that has become a big part of my life, Seer Interactive. I genuinely like and trust my co-workers and the leaders of the company.
In these situations, where real trust exists between a company and an employee, there has to be a better way to quit…right?
I was recently faced with my own dilemma of how to face a potential departure. In March 2017, I spontaneously purchased a one-way ticket abroad for $150 that would take me on an adventure 5 months later. I had always wanted to travel the world while working and this proved to be the catalyst needed to take the first step.

Once the ticket was purchased I had to decide what to do next. Do I leave Seer and the raise and promotion that were heading my way? Do I jeopardize my relationships that I had built by not telling the company and then giving them a generous 4-week notice? I was 25, single, and healthy, without any obligations or commitments other than to myself and my company. It seemed like a small window of opportunity and I needed to make a decision.

After talking to many internal confidants at Seer, I was encouraged to tell our Director of HR that I was thinking of leaving. It was April, my flight was in August, and I was scared.
The conversation about quitting ended up being the best conversation of my entire career.
By being open about my potential departure and career goals I earned the respect and trust of the leaders of Seer. Not only were they incredibly understanding of why I wanted to embark upon this adventure, they were open to finding a way to allow me to continue to work part-time at Seer while I travelled the world.

What would I have missed if I had been weird about quitting? Well, right now I am in Brazil working remotely. I’m travelling the world — fulfilling both my personal and career ambitions. I couldn’t be happier or grateful for this opportunity.

But it wasn’t just me that benefitted from not being weird about quitting, my company did too. Oddly enough, changing the conversation around how people quit can be a powerful retention tool.
If you’re a company or manager who, like Seer, wants it to be ok for employees to talk about moving on. Here’s my advice:

1.Demonstrate your values through action. One of the best ways I’ve seen Seer do this is through company benefits that show that they trust their employees: unlimited paid time off, flexible hours, personal development budget, and great health care all communicate: “Hey, we care about your well-being and trust you to do your job well, so we’re going to treat you like adults.”
Another one of my favourites from Seer is their commitment to the growth of their employees both during their time working there and after they depart. The alumni network is a living breathing action that shows employees daily they are valued on a personal level — whether they work at the company or not.

2.Be vocal about your stance on quitting. Make it clear that your company thinks about quitting in a different way. I recently *starred* 😎 in a video Seer created about my experience having this conversation. This is public information inside (and outside) Seer and acts as an example for other employees who want to “quit better.”

3.Build an amazing team. Being surrounded by an amazing team is a huge intrinsic motivator that encourages employees to be their best selves. Respecting both your managers and your colleagues, and valuing the relationships within the company provides an additional motivator to want a respectful departure.
Companies should place emphasis on hiring for culture and cultivating relationships amongst employees. Team events, employee bonding, and coffee chats should be encouraged to support organic relationships between the team.
When I started at Seer, I was assigned a ‘scavenger hunt’ that provides newbies with an excuse (and budget) to go out to lunch, coffees, and happy hours with team members they work with and those they wouldn’t normally interact with. 

It starts to build a tight-knit group of individuals that even if you don’t work with someone you start to get to know them on a personal level and understand what they do for potential collaborations in the future. There’s also a ‘buddy system’ where new employees are paired with seasoned employees for regular chats and support.

4.Practice empathy. Empathy is one of the most valuable characteristics a company can have when they want to build trust with their employees. Understanding and showing that they value their employees as individuals and not just workers build a relationship between employees and companies and shows employee’s that they are respected, appreciated, and heard.

Seer does this through responding to situations in a very human way. Are you out sick? They’re not questioning your motives when you take off a day. Last minute family emergency? No problem. Take the time you need and don’t feel guilty about being away. They communicate that the team’s got your back, and we want you to be healthy and present in your life.
This makes it clear long before quitting time that if you surface a problem, leaders at Seer will view your situation with empathy.


How many people do you know who have been at the same job for 10 years? 5? 2? Tenures are getting shorter and shorter. Transitioning in and out of companies is inevitable and having these conversations will support your employees and might just be the retention strategy you didn’t think possible.
It’s time to make it okay to quit.

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