Forget about your “career path”. Embrace a career stumble

daniel debow
Published in
7 min readSep 6, 2017


Written by Daniel Debow & David Pardy

Smart young people (aka GPSGs — read more here) approach me for career advice a lot. Some ask how to become an entrepreneur, an angel investor, or even a VC (which I have never been). These 20-somethings are looking for something that can’t be found: a “path” to the career they want. This is an unfortunate myth. Any honest advisor will say that you can’t plan from that far out. You have to stumble into it.

This lesson sunk in when I was a co-founder at Rypple. At the time, I was trying to recruit a superstar young designer. I enlisted one of my experienced investors to assist. After a brief “closing” call, the investor was deeply frustrated with the candidate. “He’s got the career path disease,” he said, “He wants to control for every variable in his career.” This investor had enjoyed an amazing career. But he didn’t plan it that way. “I didn’t have a career path. I had a career stumble. These kids are crazy.”

These words zapped my subconscious like a lightning bolt. I had the career stumble too.

Here’s my story (insofar as it relates to career-building). First I got a psych degree. Then I didn’t know what to do. I worked for my college fraternity for a year. Then I did a JD/MBA dual-degree at the University of Toronto. I got summer jobs at Sullivan & Cromwell and Goldman Sachs. I realized the white shoe advisory environment wasn’t for me. Before graduating, I luckily re-connected with David Ossip. He invited me to help write the business plan for his startup Workbrain (along with his co-founder David Stein). I ended up as VP Marketing. I hated marketing from B-school days, so I took a leave to do an LLM at Stanford in Law, Science & Technology. Maybe I could be a professor? Then Workbrain went public and I returned as VP Corp Dev. Then we sold Workbrain to Infor. After, I co-founded Rypple with David Stein and George Babu. We sold Rypple to Salesforce. I stayed there as an executive for three years and also started angel investing on the side. I opened a music studio that had a new business model I thought made sense. I taught as an Adjunct Professor at the University of Toronto law school. Now I’m starting a new company here at Helpful.


Handing in my keys after 3 years at Salesforce.

There is no Master Plan

Did you see the semblance of a master plan in that story? I didn’t. There’s no way I could have predicted that I’d now be on my third startup. No crystal ball told me I’d invest in 50+ startups. When I learned about business organizations and finance during my JD/MBA, I envisioned future Daniel clothed in a power suit, working in a corporate tower vigorously and unsentimentally pumping out deals. I wasn’t charting a path to build my own company from within a cramped office wearing shorts and flip-flops.

My path was not a plan. It was a stumble. I just kept my eyes open, worked hard, and leaped at opportunities that excited me.

University of Toronto convocation, about to jump head first into the startup world with Workbrain.

Embrace the Career Stumble

The linear career path is a myth. Corporate ladders are gone, or they don’t lead anywhere. Young people are catching on. What about managers?

Some companies actually are getting the picture. The smartest ones are ditching the formulaic ladders. They allow career flexibility. The new corporate ladder is a lattice. The lattice lets you move in any direction without losing momentum. (p.s. For my software people, this is just like waterfall vs. agile — you build, deploy, learn, repeat).

A career stumble may sound haphazard, but to my young readers: there’s no need to be alarmist about your future. Some skeptical GPSGs have told me that, without planning, all one can depend on is sheer blind luck. While there’s a breath of truth to that, the crucial detail is knowing how to create your own luck.

Hold on, I know you’re not a Leprechaun — keep reading.

You can create your own luck by creating and seizing opportunities. For the curious and determined people amongst my readers, here’s how.

1. Find an Immediate Focus

2. Work Your Ass Off

3. Repeat

1. Find an Immediate Focus

Sit down and find an opportunity you can devote yourself to for a couple years. Just do something you care about. Don’t worry about what it will look like on your CV (I’m pretty sure I just heard my B-school career counselor gasp). Prioritize what you get out of it personally. Whether it’s about the people, the opportunity, the cause, or the technology, pursue something that deeply interests you. If you move toward the good life, you’re unlikely to regret your decision.

Don’t believe me? That fine — I’m just one person. Dr. Jeffrey Jenson Arnett is a psychology professor who researches this subject using broad data. He studies the period between 18 and 25, which he calls “emerging adulthood.” I love this quote from him:

“Emerging adulthood is a time of life when many different directions remain possible, when little about the future has been decided for certain, when the scope of independent exploration of life’s possibilities is greater for most people than it will be at any other period of the life course.”

He’s more poetic than me. I’ll just say: when you’re young you’re at the prime of your life and you can afford to fail, so just intensely do something you don’t think you’ll regret. Don’t worry about the risk. Life will only make it harder to take risks. So take them now, before it gets too hard!

At this point, you might expect me to proclaim, “And therefore you should do a startup.” Aha, not quite. Startups are not for everyone. Do your own passion. Ponder these questions:

  • What motivates you?
  • Where do you like to be?
  • Do you think you can learn from the people around you?
  • Will you do new things?
  • Do you believe in the company’s vision?
  • Does the mission excite you?
  • Will you respect yourself?

My strong advice is not to belabour these questions. You can spend a lifetime answering any one of them. There’s no formula here. You can’t actually plan your path. Your path happens to you. Ultimately, your emotions will make this decision for you. Trust your gut (it has more neurons than a dog’s brain, so it can actually process information and help you make decisions).

Final point: you need to get paid in this adventure you choose. Chances are, if you’ve graduated university, then you’ve got debt. Don’t use that as your sole justification to take the highest-salaried offer, but don’t accept an unpaid internship-type position either. You need to start building personal capital early in your life because it sets a reference point for future earnings.

2. Work Your Ass Off

Once you’ve decided where to focus, give it your all. Read this other post I wrote on how to be a superstar as an early-stage startup employee. The recipe is there.

For the Coles Notes version:

When you’re a top-level employee, you don’t just identify problems. You don’t just investigate them. You don’t just sketch out a possible solution, or recommend one higher up. You go beyond that by just fixing them. You should be able to say to your boss, “I identified a problem, figured out what caused it, researched how to fix it, and I fixed it. Just wanted to keep you in the loop.”

Getting here takes a lot of courage and judgment, and those are hard skills to develop. Most new, young employees are more comfortable being told what to do. Even experienced people can be uncomfortable making and acting on decisions themselves. That’s your goal nonetheless.

Vigorously develop yourself and your projects. Work harder than other people. If you simply can’t drum up the energy for it, chances are you’re doing the wrong thing. That’s great — you learned something important! Move on.

3. Repeat

Your first career move should be a frenzy. You’ll learn lots, inevitably make mistakes, but always move fast and do well. Do that again.

Why move quickly and intensely without careful, long-term planning? Because as long as you’re learning and moving toward the good life, two things will happen.

  1. You’ll become valuable and naturally build your reputation. Successful people who notice you will introduce you to other successful people who have an interest in knowing people like you. The market for talent is powerful and incredibly close-knit. It’s this magical market that developed my faith in the career stumble.
  2. You’ll be happy. I’m talking about the long view-type of happy. Even if your day-to-day emotions are as up-and-down as a roller coaster, you’ll feel that you’re doing something is right for you, or that you feel good about. This follows almost by definition if your gut-check passes the questions above. And if you don’t feel this way, you can always repeat the process.

How do I know the market for talent will work, if you’re a 5-star employee? Because I’m in it. I see that people aggressively recruit A-players all the time. Over the past fifteen years, me and my team have been aggressively targeted. Trust me — if you’re a superstar, you’ll be batting away the offers.

When I’m recruiting, I’ve found that the combo of being passionate and having the habit of doing things excellently are together a strong signal of career fulfillment. I’d hire someone who demonstrates these qualities over someone with a cookie-cutter CV any day. Who is likely to have learned more: someone who attends university, takes an entry level job, and follows the typical career path? Or someone who dropped out of university to pursue her own software project, got some traction, built a small team, and then failed?

Got a career stumble you want to share? Let me know in the comments.

If you found this post helpful, give it some👏s & share it with your friends!

P.S. Helpful is a new company I’m working on. Check it out here to learn more.



daniel debow

Dad of 4, CEO of, ex-Salesforce SVP, founding team at Rypple & Workbrain, angel investor, bass player, adjunct prof @UofTLaw and curious person.