Prioritizing Projects (or How I Learned to Love the Hustle)

Prioritizing Projects (or How I Learned to Love the Hustle)

Prologue: In my view, tech startup culture and convention requires entrepreneurs, leaders, and CEOs-to-be to surround themselves with a stoic, steadfast, and sure-footed appearance. I’m going to break from this apparent norm over the course of writing my blog, and instead, simply opt to braindump all the things. (That is, shy of insider business information or deal-making details.)

I’ve been struggling recently.

Since graduating from the Lean Entrepreneur Program at Launch Academy late last year, and going through Lighthouse Labs full-time web developer bootcamp, (essentially twice, since I rolled back from the November to February cohorts,) I’ve been brimming with ideas and interesting projects that I’ve been passionate about pursuing.

Now that I can code, (admittedly at a pretty slow pace compared to many of my contemporaries,) and now that I can explore, evaluate, and act upon apparent business opportunities through the lens of Lean Startup, I’ve been even more pumped up to take a shot at building something worthwhile, something that can scale to serve (hopefully) millions of people around the world.

The struggle is essentially that I’ve been chasing after too many interesting and different projects.

This has lead to my skills and context growing at a pretty remarkable pace. All of a sudden, I’ve found myself wholly confident in my capabilities to code in Ruby, Rails, Javascript, Node.js, various devops skills, advanced Bash scripting, Jekyll blogs, Meteor-based sites, take on more ambitious computer networking projects and high-definition realtime video broadcasting systems in my consulting role at VMS, and so on.

The flip side is that I’m stuck, making an impact that’s a mile wide and an inch deep, to borrow a turn of phrase.

Sidebar: Don’t get me wrong. I’ve definitely found my sense of “home” at Launch Academy. I’ve found my time here to be nothing short of a spectacularly invigorating, supportive, and a wonderful environment all-round. It feels like I’ve found my peers, and in a substantial, intellectual and emotional sense, I feel like I’ve found my family. But I know that working from a hotdesking area in a beautiful office doesn’t mean that I’m getting traction with any particular project.

Another issue; my depression has unfortunately kept throwing various proverbial wrenches into my productivity.

I’ve generally been doing substantially better over the past year of my amazing time at Launch and Lighthouse, than I had been doing over the previous 10 years, in terms of my mental health.

However it’s not all rainbows and smiles.

I still regularly find myself crashing badly, needing to go home and sleep at inopportune times. When I’m awake and still feeling awful, I wind up questioning everything that I’m doing, or trying to do. The roar of negative introspection can be deafening at times.

Most of the struggle is in getting back up, dusting myself off, and somehow getting back the office (downtown Vancouver) to try again. Even if only for a few hours, rather than the usual 12-14 hour-long days I’m used to pulling, getting back into the office has been a huge (if quiet) source of support for me to keep moving forward.

Another huge source of support and therapy has been music.

I’ve been a fan of Max Graham since his remix on Travelling, from way back in 2000. I’ve been lucky enough to see Max perform at Celebrities here in Vancouver twice over the past year-and-a-half. I’m certainly not shy of sharing my love for his Cycles Radio Podcast either, which always helps to get me back in the groove with work, reading, focusing my mind, dampening down the shitstorm of “how do I move forward” and noise that often plagues my day. (I even have it cranked up on my headphones while I write this post!)


Anyway, back to the main point of this post.

Prioritizing business projects.

I think I can best voice my concerns through a few open-ended questions, rather than stating anything even remotely concrete about where to go next. Here goes:

  • If you have to take a Lean approach to everything, and you’re ready to invalidate your very early-stage business hypotheses and move on quickly, how can you take anything but the shotgun approach to finding and building a business?
  • At what point can you truly say, “Here’s what I learned from this experience,” and truly take a more accurate swing the next time around? Doesn’t the super-grindy nature of modern entrepreneurship require a certain level of questioning your viability and legitimacy?
  • What about proving your worth to your peers, by somehow getting traction?
  • Is it illegitimate to roll with the brutal statistics about startup success vs failure rates?
  • What if you’re really an amazing founder, but simply haven’t yet found your cofounders for your project?
  • What if your immediate/local ecosystem has amazing people, but everyone’s fighting their own battles to create some movement of the traction needle?
  • What can I do today to help myself or help those around me?
  • Which of my many projects and ideas is worth chasing and trying out until it has a semi-permeable conclusion, instead of just smoke and empty hope?

I’m unsure how to answer these questions.

I wrestle with at least two or three of these on a daily basis.

I would love to hear from other leaders on how they approach these situations, and how they’ve wrestled through the (seemingly) never-ending brooding and self-doubt.

Ashley Theiss's Picture

About Ashley Theiss

Ashley is a full-stack Lean tech entrepreneur, web developer, designer, photographer, DJ, and aspiring glider pilot, active the Vancouver tech community.

Vancouver, Canada