Why I Walked Away From $25k In Company Stock

Sometimes you've got to walk away without knowing what lies ahead

In 2016, I made a decision. Actually, I made quite a few, and not just small ones – I’m talking about big, life-changing decisions. In general, those decisions panned out fantastically – like asking Kristin to marry me – but it all hinged on one key decision. I made a tough call and walked away from about $25,000 in company stock.

Where I Was In 2016

Let me set the stage by backing up to where I was in January 2016 in my life. Three years earlier, in 2013, I had moved out to California with nothing except what I could fit in my Sonata. I’d kept my job, and was working with offices in the Los Angeles and San Diego area.

Being able to keep my job was a huge boon. Without it, I probably wouldn’t have made the decision to move. Some plans that fell through and a bizarre May snowfall were the catalyst I needed to move.

But after three years, a lot of things had changed with my work. I no longer was working with the offices I had been. My travel was cut down from 50% of my time to about 10%. The pilot program I had signed up for evolved, but with it meant a less involved role, doing less and less of the nitty-gritty work that I enjoyed.

I found myself working at home more and more, and over time as the team expanded and grew, I wound up with a new manager and new responsibilities. In short, what I ended up doing in the last year or so was nothing like what I had been doing, and it wasn’t the best use of my skill set either.

Like many people I wasn’t explicitly unhappy at my job, but I also definitely wasn’t happy either. I had grown increasingly disengaged despite asking for more, and different types, of work.

The Job Offer

And then in February 2016, something out of the blue changed. I got a text from a former co-worker saying she was going to hire me at the start-up she was working at.

I laughed.

Admittedly I didn’t think it was a serious thing. And why would I? Who even does that, much less via text?

Turns out my former co-worker does.

In the following weeks we had several conversations and I realized that she was actually being serious. I had joked with Kristin shortly after the first text, mostly to gauge how she’d react. A new job would be a huge life change for us considering it’d require a move back to Minnesota.

As luck would have it, I was already planning on getting up to Minnesota, and used that opportunity to meet the team. We hit it off and within a couple of weeks I had a firm offer as a product owner.

I was ecstatic and terrified all at the same time. I had only worked at one company and honestly saw me working there for the rest of my career.

Kristin and I even talked about me moving into a management position back at the company’s corporate headquarters once we wanted to move back to Minnesota in 5-10 years.

Excited, terrified, nervous, anxious, grateful, overwhelmed…I was a hodgepodge of emotions.

Pros and Cons of Career Change

Making any career move can be scary. More than just moving companies, shifting to a brand new role presents a slew of unforeseen challenges. I didn’t hate the job I was at by any definition of the word, but it was boring. I hadn’t been really advancing in about a year and a half, and I knew that at some point my chickens would come home to roost.

But the thought of going from a Fortune 500 to a 15-person start-up was scary. And thinking about what I’d have to give up for the opportunity – and the risk – was daunting as well.

Despite being somewhat stagnant at my job, I’d managed to receive stock awards as part of my compensation package. I was very thankful for these, and worked to make sure I could earn them every year.

Companies frequently grant stock awards that vest over a period of time. The vesting period is a sort of retainer mechanism – if you leave the company before the shares vest, you forfeit your shares. This is awesome for long-term employees, but as someone leaving the company, it’s an extra consideration.

When I logged into my account, I saw the unfortunate truth: leaving would require me to walk away from about $25k in unvested stock. Could the pros out-weigh the cons? It was time to see if that offer was good enough to move me away from the ocean and back to the frigid winters that had made me move in the first place.


Salary: While this was a healthy increase in base compensation, it didn’t include any sort of ownership right off the bat, and didn’t have any sort of bonus structure. I’d have to work at the start-up for well over a year to just break even on the stock I’d walked away from. That didn’t include the potential of receiving additional stock at the old company.

Still, a healthy base compensation increase was attractive and unexpected for a start-up.

Career Progression: I didn’t really know what I wanted to do with my life before the job offer. I felt stuck in my job, and didn’t know where to go. But the way I figured it, a new title and new responsibilities would be great for my career. Even if I fell flat or the company failed, I figured that at a bare minimum showing some more progression in my career could only be a good thing.

Start-Up Experience: I’ve found that recruiters and hiring managers love start-up experience. Start-ups are scrappy and devoted, and they require scrappy, devoted, and intelligent people to run them. When you work at a start-up, you learn weird stuff that you don’t learn at a large organization.

The reason is simple – they don’t have the luxury of employee specialization. When you work at a large organization, they’ve got resources to hire people for specific job functions. Most of the time that’s not the case in start-up world. It’s like running a blog. One day you’re a content creator, the next you’re a marketer, and after that you’re tech support.

If you can successfully apply even a small portion of that experience to a new endeavor, you’ll be viewed favorably in the eyes of recruiters and hiring managers.

Job Market: Before I decided to move to California, I had a half-hearted attempt at finding a job out there – just in case I got the ‘no’ from my old job. Turns out for my line of work, the jobs just weren’t that prevalent.

Compare that to Minneapolis which is home to 27 Fortune 1000 headquarters and a huge number of smaller companies. Needless to say, if things did go south, finding new employment would be a lot easier up here. Plus, virtually my whole professional network was in Minneapolis.

Cost of Living: A few weeks prior to all this going down, Kristin and I noticed a house for sale in our neighborhood out in California. It was a small house, about 800 square feet. We looked it up online. It was a disaster.

And yet, the house sold for nearly $800k. It was promptly destroyed and a new home built.

That was pretty much par for the course in areas we wanted to live in. Easily $750k for land and a tear-down house, or a bit lower for something with shared walls. We aspired to own a home, and it just flat out wasn’t possible without some sort of major income changes or change where we wanted to buy.

That all worked out fine, in case you were wondering.

Throw in no sales tax on clothes (which Kristin loves, but I don’t care about too much except when I need to buy new pants) and it was no contest that Minnesota was the victor.


Bye-Bye, Stock Awards: Ah yes, my stock.  Walking away from $25k in stock would take over a year to rebound from, even if all things went perfectly. This was a clear financial risk, particularly going to work at a start-up.

Hello, Risk: Start-up life is notoriously volatile, emotionally taxing, and quite frankly can be exhausting. I was walking into a total unknown. Would I like my job? I’d never been in this role before. Would the company even exist in 6 months? There clearly was risk here that needed to weigh into the decision.

Moving Away: We built a life together in California. All of Kristin’s family and friends were there. This move, if we were to take it, would be much more emotionally taxing for her than for me, and I was not going to force her to move with me if she wasn’t 100% on board. I was ready to turn the job down and stay in California if that’s what she wanted.

She did want to come with me, and knew that the pros probably outweighed the cons in this case.

The Real Reasons Why I Left

And she was right. The real reasons I left were for the career progression and the cost of living. I had friends and family here; making the move was easy for me from a personal perspective.

If you know my story, you know that things obviously didn’t pan out how I’d hoped. In February 2017 I was laid off – 11 months after starting. I came up at a loss on the salary front. I don’t think I’ve “recovered” from where I’d have been had I stuck with my initial company.

But at the same time, my future looks a lot brighter and full of opportunity. I’ve met some absolutely amazing people and built great friendships.

My Lessons

If I had to summarize, here are the biggest lessons I got from this whole experience:

  • Always be open to opportunities that scare the crap out of you. Sometimes they turn out awesome. Make sure things pass the sniff test before getting overly excited, though.
  • Things rarely work out how you hope. Sometimes they turn out better, sometimes worse. But rarely exactly how you hope.
  • Set yourself up to be able to afford to take risks. If we weren’t already saving money and in an okay place financially, this would have been a lot more stressful.
  • Nurture your friendships and relationships, both personal and professional. These are surprisingly fragile but strong bonds are tough to break, even with 3 years and 2000 miles in the way my former co-worker thought of me.
  • Life can change a lot in a short amount of time.


What factors do you consider when weighing big life changes?

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  1. You may not have recovered from where you were, but if where you were would get you a crappy 800sf house for $800K, you are waaay ahead of the game.

    The most important lesson to me is that as a couple, you are learning to be open to flexibility early in your marriage. Because if you don’t learn that early, as years go by you’re more likely to avoid making changes for the better. But I don’t think you could do this without the right partner. Kristin is a keeper.

    1. It’s crazy to me how expensive those homes are, I just don’t get it…

      And yeah I was really happy that Kristin was down to move – especially since we didn’t get engaged until after we decided to move (About two weeks before we moved, and one of those was spent in Hawaii). She’s definitely a keeper!!

      Thanks for stopping by as always Mrs G!

  2. Love the honesty! Life never really goes exactly how you planned but that’s the test to see if you can grow and pull through. Funny how that works, I’m starting to feel like we’re all just reality TV shows for the aliens up there.

    “Always be open to opportunities that scare the crap out of you”

    Hopefully not…literally haha.

    1. Hahah, I think that a reality TV show of my life now would not be that amusing. My roommates and I did want to make a reality TV show when we were in college though lol.

      And hahahha yeah definitely not literally! LOL

  3. I loved reading this, congratulations on taking a chance and a career risk. It also says you do a pretty good job of retaining relationships with coworkers and a network to find a job like this.

    Don’t worry too much about the stock, that’ll happen to a lot of people. I’m sure it was restricted, so you can’t think of it as your money until you work past that vesting date. I’m going to walk away from $300,000+ because I don’t want to work until 55.

    1. Thanks Mr Shirts! I think I came out the other end okay but it still stings a bit at times, especially considering the stock would be closer to 38k now haha. 300k is a lot though, but hey if you can afford to do that, that’s a great position to be in, too.

  4. You made the right choice for your life. Too often we look at things in the rear view with today’s foresight and regret it. Thanks for sharing this incredible story!

  5. I really enjoyed this! Sometimes you have to take a few chances, my wife and I have done similar things. We just recently moved to take advantage of a better work situation for my wife and now I work from home. I wish you the best of luck!

    1. Working from home is an awesome perk 🙂 It’s really underestimated IMO, as long as you are the type of person who can do it well. It’s not for everyone. Glad to hear it’s worked out well for you guys!

  6. Interesting story Dave, thanks for sharing.

    I have similar thoughts on the subject of leaving a great job and pursuing entrepreneurship – and it’s so true – you learn soooo much more when you are required to be the keeper of many hats 🙂

    1. Thanks Erik. You definitely learn a lot. I think I’d be all about that entrepreneurial lifestyle, but I need some runway in savings first. Not quite where I’d want to be to take that risk quite yet! 🙂

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