How I Left My Job & Negotiated My Exit

Jennie here.

From day 1 at my (now former) company, I knew that I was going to leave. It wasn’t that I didn’t enjoy my job or that I didn’t always give 110% of my effort. I just knew what I wanted:

Ivan and I wanted to travel the world (and work simultaneously) starting in September 2018.

So, Ivan and I have had this planned out for more than two and a half years. At the end of July, I finally informed my manager of my intentions.

Given my current manager-employee relationship, I decided not to disclose that I was traveling the world. That’s my personal life, and it was really none of their business.

However, I did share the reasons why I was planning to leave. I stated that I’d changed managers three times in the last year and my relationship with my direct manager always seemed out of sync. I felt like she never really trusted me - her only team member. I also shared that I was exhausted by the constant need for political maneuvering. This is a problem with “careerists” in any industry - everyone’s just angling for the next seat. Whether that’s on a rocket ship or the Titanic hardly matters because nobody has skin in the game.  

I was just tired of it. It all seemed so pointless.


Here was my ask to my direct manager:

  1. I was willing to finish out all of my projects over the next month and help train/transition any new hires.

  2. During my last month of employment, I wanted to work remotely from New Mexico to spend time with my family.

  3. If they wanted to keep me on to tie up loose ends through August, I wanted an extension on my benefits and be on payroll through the end of September.

Truth is, I wasn’t sure how it was going to turn out. Ivan and I were prepared for any one of  three scenarios:

  1. They would let me go on the spot (very likely).

  2. They would let me finish out my work over the next month (not so likely).

  3. They would attempt to persuade me to stay (not so likely).
     


The Results Of My Negotiations - What I Got Paid To Leave:


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In the end, it didn’t turn out 100% the way I wanted. Maybe just 75%. But that was more than enough, considering that Ivan and I would’ve been perfectly happy walking away with nothing:

  1. My manager gave me a one week to “finish up my tasks/projects.” There had been a lot of tension for some time so this worked out well because I got time back in my life.

  2. I coordinated with our HR department and managed to get one month’s pay without the work.

  3. They did not choose to extend my benefits into September (this was always a stretch goal and not a completely necessary one. Our international health care plan begins coverage starting September 1st).

I knew that it was highly unlikely that they’d accept all of my terms and I was right. Ivan and I had anticipated that my manager would be inflexible and might respond negatively to my resignation so we actually pre-emptively cancelled the lease to our apartment at the end of July.


Lessons Learned and What I Would’ve Done Differently In Leaving My Job:


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Here are some of my lessons learned from my first tech startup:

  • Lesson #1: I wish I had better negotiated my employment contract from the very beginning. My former company (like most tech startups) aspired to the “hire fast, fire fast” philosophy. And here’s the thing - those companies will always exist within the startup world, but there are consequences to this type of mentality. In theory, it’s a great idea to cut your B and C players quickly. But this assumes that management is competent and has the ability to distinguish between A and B players - and not be caught up by their own biases and prejudices. Sometimes objectivity and rationality is just a cloak for arrogance and a poor understanding of your own limitations.

    Had I known what I know now...I would have demanded a severance package and better sign-on bonus (relocation package) from the beginning because I was accepting a job across the country. In my next opportunity as a director level or higher, I will definitely negotiate terms that are more favorable to me.
     

  • Lesson #2: I should’ve done better due diligence. I joined the company because I was desperate to leave Boston at the time - my job was going nowhere and my managerial relationship was hostile (Ivan: misogynistic) to say the least. And in this new opportunity, I jumped without thinking too hard about it - I didn’t even negotiate my salary - which I should have.


8 Steps to Negotiate & Execute Your Job Exit Strategy


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Everything in business is negotiable. Trust me, you have more power than you can imagine - no matter what your situation.

Here are a few steps that I’ve gathered to help you negotiate your exit when you decide to leave your job.
 

Step 1: Decide on what you want and make your plan.

For me, I wanted to leave and travel the world by September 2018. You don’t have to wait as long as I did but I felt grateful to have two and half years to do good work, queue up the “next thing” in 2018, and mentally prepare to leave my job. Because I’m a planner, I needed this sort of thing. And I knew that if I didn’t have a “deadline,” I would never leave.
 

Step 2: Always lay the groundwork.

One of the most important things that’s always relevant - whether or not you leave a job or want to negotiate a raise - is you should always do your job well and document everything. Make sure to always document the following:

  • Schedule quarterly reviews with your manager.  
  • How well have you performed in the last 6 to 12 months? What are your metrics?

  • Have a presentation that covers your accomplishments and accolades, with testimonials from other team members across the organization.

  • Send a follow up email of what you discussed and shared with your manager. It’s critical to have a paper/digital trail of your good work.
     

Step 3: Prepare for your “next” thing.

Are you looking to get a new job? Traveling? Give yourself at least 3 to 6 months of interviews, informational coffee dates, or start doing some freelancing. Start early because it’ll only give you more options down the road.
 

Step 4: Assess your relationships.

In any organization or team, you should know who you can  depend on to advocate for your work and accomplishments (before and after you leave). Also, it’s good to have relationships with your executives if you work for a small tech startup. This makes it easier for them to accommodate to your asks when you finally decide to leave.
 

Step 5: Understand your leverage.

Understanding what your advantages are in any given situation. For example, was a lot of your team’s work dependent on you? Are there key company events/milestones during the year where your presence is essential? That’s leverage. And with proper timing, you can use it.
 

Step 6: Decide what you want.

Do you want a more flexible work environment (e.g. working remote 100%)? Are you leaving because you don’t agree with the direction of the company or management? Regardless of the reason, think about what you’re willing to do to help the company transition - and what you want to ask for in return. For example, if you’re a star employee - you can offer to help train the new replacement over the course of x months. And for your troubles, you could asked to be paid x extra for the additional months you’re putting in. If you’ve got a family, always ask for an extension of your benefits. In my case, my healthcare was 100% paid by my company so it would have saved me over $1,500 a month.
 

Step 7: Understand and accept the fact that the exit meeting may not go the way you want.

That’s just life - it’s not always going to work out the way you had intended. The moment you say, “I’ve been thinking about leaving the company…” it’s up to external forces and how they respond. I don’t want to downplay luck in all of this. On the other hand, they also say that luck is preparation + opportunity.
 

Step 8: Control your own narrative - remember the future and leave on positive terms.

Sure, it’s important to negotiate the best terms in your separation agreement but keep in mind that this goes beyond money – what you agree to and how you go about it can affect your career long term. When I left, I did an informal “exit interview” with every single one of the co-founders and executives at my company. I wanted to express gratitude to them, share why I was leaving, and make sure that I controlled my own narrative even after I’m gone.
 


The Bottom Line: Everything Is Negotiable; Ask For What You Want


If there’s only one takeaway that you have from this post, it’s that the world is malleable and you have more power than you think. And you owe it to yourself to ask for everything that you want because who knows - you just might get it. 

Early on, Ivan and I both realized that the “where” you end up isn’t nearly as important as the “how.” The journey over the destination applies to pretty much everything in our lives. And even when things don’t work out the way we want, you can still be confident in the fact that you played your hand the best you could. And that’s all anyone can ask for.

If there’s only one takeaway that you have from this post, it’s that the world is malleable and you have more power than you think. And you owe it to yourself to ask for everything that you want because who knows? You just might get it.