Getting Over Career Heartbreak

Most of us have had a crushing job experience at least once in our lives. Here’s mine (and what I learned from it)

Feb 4, 2021 was perhaps the worst day of my professional life. It was the day my dream job slipped through my fingers. 

Here’s the story.

After graduating from my MBA program in 2018, I took a job with Deloitte Consulting in Boston as a management consultant in their Strategy & Operations division. It was, at the time, the “biggest” job I had ever had.  

I had prepared rigorously for the last 3 years to get accepted into a top consulting firm. And after 30+ practice case interviews, hours of networking, and an intense 2-day interview at Deloitte’s office in Atlanta (they even put me up in the Ritz Carlton!), I had finally reached my long-time goal. 

I vividly remember getting the call from a senior Deloitte partner offering me the job (as my 1st kid had just been born only a few hours earlier and my wife/I were still basking in the joy of being new parents; it was probably one of the best days of my life!).

At first, things in consulting were great. The work was exciting. My coworkers were incredibly bright and willing to teach me the ropes. My family loved living in Boston. And I was getting incredible experience, working with clients across a huge range of industries (from Silicon Valley Startups to Global Defense Contractors), and getting to advise senior leaders at major corporations.

But as the next 3 years went on, it became clear that it was time for me to leave. The hours were brutal (I was often working 50-60 hour weeks; waking up at 7am and working until midnight). The travel was even worse, especially since I hated being away from my wife and our 2 young children every Monday - Friday. And I was increasingly bored by some of the projects I was being assigned to work on.  

When my wife told me she was expecting our 3rd baby in January 2020, we both knew I needed to find a new job. I updated my resume and began quietly searching for / applying to new jobs that very week.

The one thing I was determined to do was find a job that I was truly excited by. Something that would be the start of a long-term career I would be proud of. As much as I wasn’t enjoying my consulting work anymore, I didn’t simply want to jump to a job whose greatest virtue was that it wasn’t consulting. I needed to find a job that deeply fulfilled me. I didn’t want to run away from something. I wanted to run towards something.

After searching for 4 months I had landed several job offers that were solid, but none I was 100% excited by. I had turned them all down, still in search of the “perfect job”. And that’s when I found it.

A friend of mine from grad school texted me and said I might be interested in talking to another student from our MBA program who was looking for folks to join him at a Venture Studio called High Alpha Innovation (also known as “HAI” for short) based in Indianapolis. I asked for an intro, and soon was on the phone hearing about this incredible company.

High Alpha Innovation was the company of my dreams. The founder/CEO had been a partner at Innosight (the consulting firm founded by my intellectual/personal hero Clayton Christensen) and he had started HAI to put Christensen’s theories on disruptive innovation to work in the real world. 

The business model was fascinating. HAI was essentially the love child of a Venture Capital firm + a Consulting Firm. They would partner with established institutions like Fortune 500 companies and Universities to jointly fund a startup. The startup’s purpose would be to “disrupt” an industry with some kind of innovative tech/service but would also protect the parent company from being disrupted (since they would be the main investors of the startup!). 

The idea of starting new companies, consulting some of the world’s best organizations on innovation, and working directly in innovation (a field I loved) sounded like a dream come true. It was everything I had wanted in a job, but hadn’t quite known how to articulate.

I spent the next month networking with at least half the company. The more I talked to them, the more I was hooked. Not only was the work incredibly cool, but every person I met was genuinely kind, smart, and driven. I knew I would love working with the team.

My friend kindly arranged for me to get an interview and I was rapidly advanced to the subsequent rounds. Each interview went extremely well and I received a lot of positive feedback. The more I met with the team, the more it felt like I was destined to work at HAI.

After 5+ rounds of interviews, I was invited to a final interview where I would present a startup pitch / business model to HAI’s leadership group based on a prompt the CEO sent over to me (apparently it was a concept they were considering investing in). I was given the weekend to prepare for it.

I poured my heart and soul into my presentation. I researched relentlessly, scrapped then re-worked half a dozen ideas, and spent hours talking with potential customers and even investors in the space. By the time I was done I had put almost 36 hours total into my presentation (probably the single most extensive prep I had ever done for an interview). I wanted this job more than any other I had ever applied for. 

I practiced my presentation over a dozen times (to friends, family, and the mirror), and had my pitch down solid. When the interview date itself came I was a little nervous but mostly excited to show off my work. The interview itself seemed to go extremely well. The HAI leadership asked dozens of questions which I had clear answers for and afterwards, the recruiter sent me a note telling me what a great job I had done, how impressed everyone had been with me, and that they would be in touch soon.

I had given my absolute best. And to be completely honest, I felt that I had earned the role. My wife, parents, and in-laws were over the moon excited for what they felt was surely coming my way.

A few weeks passed while I anxiously waited for news from High Alpha Innovation. I’m embarrassed to admit how often I checked my phone hoping that I would see an email from them. I jumped nearly every time I got a new notification from an incoming call or inbox notification.

I was playing pickleball with a friend on a cold night in February when I finally got the email. 

I could feel my stomach twisting up as I read those words. I felt sick inside but didn’t know what to say. My friend, sensing something was wrong, asked if I was okay. I told him I had just gotten some hard news and needed to leave. I hurried away from the pickleball court and got into my car. I wanted to call my wife, but somehow didn’t feel like I could speak to her yet. I think it was because deep down I knew that I wouldn’t be able to hold myself together if I heard her voice asking me what the decision was.

And that’s when I broke down. 

I just sat in my car and cried harder than I had in years. It was one thing to miss out because I had made a mistake. But it felt so much worse knowing that I had done my absolute best and that it still wasn’t good enough. I felt so many things in that moment: embarrassment from letting myself (and my family) get so excited by this potential job, total confusion as to what I could have done differently, anger at getting rejected, and most of all a deep sense of sadness for the loss of something I had truly wanted.

I also realized that part of my emotions were tied up in fear. I had no backup plan, no other “irons in the fire”, or alternative offers I was weighing. It meant going back to a consulting job, which had become increasingly difficult and unfulfilling. HAI had been my dream. And when it didn’t happen I feared that I would never find something that felt as “right” as this opportunity had felt.

A week later the CEO personally asked to meet with me to let me know that they truly had been impressed with me and that I had done nothing “wrong” in the interview. He explained that they realized during the interview process that the role they actually needed on the team was different than what they had posted the job for. In his words “you are an amazing quarterback, but we’ve realized that our team actually needs a running back”. It didn’t help soften the blow, but it was a genuinely kind gesture, one that I’ve always appreciated.

---

The Rest of the Story

Funny enough, it was only a few months later when another unexpected opportunity fell into my lap. 

During my search the prior year I had been introduced to an executive (Tim Hansen) at Weave, a local Tech company that was semi-famous for being the first ever Utah company to be accepted into the prestigious Y-Combinator startup accelerator in Silicon Valley. We had enjoyed chatting, but Tim let me know that Weave simply didn’t have any roles open for me at the time, but had kindly offered to connect me with other companies. I had been impressed by Tim (and Weave) and we stayed in touch occasionally over the following months.

8 months later (and ~2 months after my High Alpha Innovation heartbreak), I happened to be checking LinkedIn when I saw a notification that Weave was hiring for a role on their corporate strategy team. In a moment of lucid inspiration I shot a note to Tim that just said “Hey Tim, I just saw this role in my inbox and would be interested in applying. Do you know who at Weave I could talk to about this?”

Within 5 minutes Tim responded with an email introducing me to Weave’s VP of Strategy. 3 weeks later I found myself being offered a role as the 3rd full-time hire on Weave’s Strategy Team. 

And it’s been a job that I have absolutely loved (for reasons I can write about another time)

---

What I Wish I’d Known Earlier…

Even with the passing of time and the happiness I feel from my current role, it’s still hard for me to spend time thinking about the night I got rejected. I can still taste the sour feeling in my mouth/gut from first seeing the words “I hate to deliver news like this…” 

But time also has given me the benefit of hindsight and further experience. And there are a few things I wish I could have told myself that night (even if they wouldn’t have completely made the heartbreak go away). As I’ve typed these out it’s funny to see how akin getting over a career disappointment is to experiencing the ups/downs of love. 

Here is what I would have told (or written) to myself:

#1) There are a lot of other fish in the sea

This company that just rejected you right now probably feels like the only one in the world that would give you a career that would fulfill you in every way. And it probably would have been an awesome place for you to be. Not going to lie about that. It stinks to be rejected.

But there are literally thousands of other companies out there (most of whom you don’t even know about yet). Next time you drive on the highway, just look out to your left and right and see how many businesses (both big and small) there are. Look at how many different industries they are in. The world is a really big place. 

Each one of these could be a place that you could quickly rise to the top of. There are a TON of ways to make money and have an impact for good. So even though it stinks now, don’t for a second believe that this was your one and only chance to land a meaningful job. That is mathematically impossible.

#2) Serendipity is a powerful matchmaker

I’ve spent a lot of time networking with men/women who have built very successful careers and lives. One of my favorite questions to ask them is “how did you get to where you are today? What path did you take to get here?” And you know what? In almost every instance they will respond to me with some version of

“you know, you won’t believe it but I took the quirkiest, most winding path to get here. In fact, I started out planning to do something else entirely, but I’m really grateful that I didn’t end up going down that road. There’s nothing else I’d rather be doing.”

In other words: Serendipity

The thing I’ve learned about myself is that I’m really crummy at predicting the future. We all are. If I wasn’t I would just make a pile of money by playing the stock market and only picking winners. But God has a way of taking us where we need to be.

For example: I had no clue at that time that a simple conversation I’d had months earlier (with the VP at Weave) would end up being the key thing that would lead me to my current company/role (a career that I absolutely love!). 

Our lives and careers can’t really be planned for. It’s good to have plans/goals because it causes us to move forward in life. But the reality is that many of the places we are supposed to go are going to be unexpected and unknown to us right now. So you should always stay flexible and open to promptings. Things happen that we just can’t plan for. And that’s a good thing.

Take faith that good things will unexpectedly happen as long as you’re trying your best. 

#3) There might be a reason it didn’t work out

As a person of faith, I have a tendency to believe that things happen (or don’t happen) for a reason. Most of the time we don’t always know what those are. But it’s good to remember that maybe there is a reason you didn’t get your dream job.

A quick separate example: A few months prior to my heartbreak with High Alpha Innovation I had interviewed with a prominent Utah-based Venture Capital/Private Equity firm. Things had gone really well and they had even flown me out all the way from Boston to meet with the top leadership. After a full day of interviewing / “wining & dining”, they actually made me a verbal offer and said they’d send the paperwork soon. I was pretty excited!

And then something happened that’s never happened to me before professionally. They ghosted me! I literally heard nothing from the company for 8+ months. After a few weeks, I emailed a few folks and still got nothing back but crickets. It was honestly one of the most unprofessional recruiting experiences I’ve ever seen/heard of (they literally flew me across the country and couldn’t even find the time/courtesy to send a rejection email!). You expect that from an inconsiderate teenager, but not from a professional company.

Almost a year later (!!), one of the senior partners sent me an email out of the blue that essentially said “our bad for not getting back to you, things just got really busy and you got lost in the shuffle; blah blah blah…” They knew it was a weak excuse. And I knew it too.

When I told this experience to a friend in Boston (who worked in VC/PE) he simply smiled and said. “I have to tell you that I’m really grateful you didn’t end up getting a job with them. I didn’t want to tell you at the time because I knew you were kind of excited by that company, but they actually have a semi-scummy reputation in the industry”. He then proceeded to tell me a few experiences he (and others) had had working with this company and I walked away feeling extremely grateful that I hadn't ended up working there.

Sometimes you don’t get the job because God/Fate/the Universe knows it won’t be good for you. And sometimes you don’t get the job because there is actually something much better for you around the corner.

#4) It’s okay to be sad for a while. Just not for too long

Despite everything I wrote above, I still would feel pretty crummy after not landing my dream job. And that’s okay to feel that way for a while. Take some time to grieve the loss of something you wanted. 

Grab a bowl of ice cream + your favorite Netflix show. Cry it out if you need to (I did). Most of all, spend time with friends/family who will remind you that there is still a bright future for you out there. And then after a week or so, get back on your feet and try again.

It all works out in the end.