My Story


I don't think people really read my resume. It's about four pages long. I know, I know; it's too long. There's a lot of really interesting stories behind it, though!

I've worked for startups, enterprises, consulting firms, small clients, coding schools, and a FAANG (kinda). I'm working at Woot, twice removed (TEKSystems -> AWS Proserve -> Woot). I also got an offer from FB, but turned it down.

This page covers my journey and a lot of lessons learned along the way. You might find it interesting. One peculiarity is that some of the lessons weren't apparent immediately in retrospect, but took time to percolate. That might be reflected in fewer or less significant lessons in the more recent episodes. And, you might notice that nearly all of the lessons are connected with my failures and shortcomings. I've had quite a bit of successes, often in spite of my pride and convictions, but that list is, strangely, much shorter.

At any rate, this is my attempt to distill all of the lessons from my career. I may add to it, as the profundities dawn on me, and as I pile on more, ahem, learnings.

Everything here is my personal opinion, and has nothing to do with any of my employers' views, past or present.

Table of Contents

  1. College
  2. Tech Writing
  3. Cerca
  4. Avanade
  5. Gesto
  6. MaxSam
  7. ReCharm
  8. Galvanize
  9. Cadence
  10. PushPay
  11. GottaGoGov
  12. Stackline
  13. Elevāt
  14. Empathize
  15. Coinstar
  16. LivePerson
  17. Wellsaid Labs
  18. Lowe's Innovation Labs
  19. NiftyPerks
  20. AWS Professional Services


tl;dr (lessons learned)

  • Success and skills are often a product of just putting in the time
  • Toot your own horn; no one will invest the time an effort to discover your story, but if you tell it well, they might respond
  • College is not a magic bullet, and not for everyone
  • Childhood gave me a superiority complex, took some serious exposure to shake that out
  • Getting relevant job experience/internships as early as possible is invaluable

I went to college at the University of Washington. What might be surprising is that higher education was never on my radar until just after I graduated. I had...humble plans based on unskilled work and trying to make it big as a musician. It seems silly, 20 years later, but that's just where I was at the time.

Long story short, someone who quickly became a lifelong friend had the chance to meet me at the exact right time, learn of these plans, and, with a perfect touch, suggested that I consider taking the SAT and seeing how I fared. "If you score well enough, colleges will pay you to go. It's essentially free money." Intrigued, I spent the summer after graduation practicing and drilling, day in and out. And, it did work. I scored a 2280, not quite a perfect score, but in the highest percentile.

I stumbled through the admissions process. Not leaning hard enough on my hardships and challenges, I submitted half-hearted essays and got into only several schools. I decided on the UW, as it seemed to be the biggest, broadest environment where I could really stretch my wings. And, it was close to home.

Tech Writing

tl;dr (lessons learned)

  • It's not about how hard you work; it's whether you're delivering something useful, and often in an arbitrary time-frame
  • Recognition doesn't go hand-in hand with contribution; it's often seniority-based
  • Cold calling/emailing works _ You can spend so much time stewed in your product that you don't appreciate the first-time user experience – yes, the benefits and systems make sense to you, but it's just words to someone who's never seen it before.


tl;dr (lessons learned)

  • Just because you can imagine something that's internally consistent and sound, doesn't mean it's practical or realistic. Our imaginations fudge a lot, and miss a lot of key details
  • Don't waste time structuring a business that doesn't exist – go prove the model
  • Just because you see and can address flaws in an existing system doesn't mean that you've come up with something viable


tl;dr (lessons learned)

  • People won't see how hard you work (and wouldn't care, anyway); they see your results, and only care if that helps them and their goals
  • Dressing well is nice, but it can't make up for skill and experience
  • There is usually a way to squeeze in learning opportunities, if you don't mind doing extra work (UX group, Node.js)


tl;dr (lessons learned)

  • Don't reinvent the wheel, especially when starting out
  • Don't be afraid to take a better opportunity; don't let your hangups get in the way


tl;dr (lessons learned)

  • Doing what's best for the client actually means taking into account what's practical and makes sense to the client, not just what's "best" overall
  • A lot of beaurocracy exists to justify itself; it often masks inefficiencies in process
  • Grifters gonna grift


tl;dr (lessons learned)

  • Just because you can sell to a client, doesn't mean you should
  • If you can't educate the client on your side of the business, you'll have to do it their way
  • Outsourcing is not a silver bullet – requires attention and management


tl;dr (lessons learned)

  • Some will love you and some will hate you; that's just how it is
  • It's easy to get to thinking that you're exceptional, or unique, but you really need to take your self-view and confront reality with it
  • Not all people can be taught




tl;dr (lessons learned)

  • Sales-driven organizations can be effective, but aren't entrepreneurally "pure"
  • Commutes suck, and they suck more the longer you have them
  • Geographically-split teams are hard to run, hard to be a part of


tl;dr (lessons learned)

  • Useful != valuable
  • Don't expect someone else to pound the pavement for you, even if it's their idea
  • Understand the long-term maintenance profile of everything you build


tl;dr (lessons learned)

  • Set expectations early; don't let a superior judge you by criteria that you don't know about
  • Appearances matter; again, people don't see your hard work, they see what they see


tl;dr (lessons learned)

  • Over-delivery is not a virtue; move in sync with your team or risk upsetting people
  • Be careful about how you word things, especially with new people
  • You can't make people from non-Tech industries understand tech growth strategies


tl;dr (lessons learned)

  • Ship early; just get it out there
  • Don't commit to a project you're not interested in




tl;dr (lessons learned)

  • Again, sales-driven companies are not optimized for quality or customer success, but for sales
  • Changing a large organization is a tremendous undertaking; harder still if there's no institutional support
  • Leaders each have their own success strategies and philosophies – some will lead to failure and departure in the short or long-term, some will lock them into holding patterns, and some will actually achieve success. Largely dependent on demonstrable impact: not, "did you make things better," but, "what can you prove you improved?"
  • Geographic distribution doesn't make for cohesive teams; instead creates pockets of concern
  • Bringing your own people makes the job 1 million times more enjoyable*

Wellsaid Labs


Lowe's Innovation Labs

tl;dr (lessons learned)

  • Confrontation/conflict can be an amazing thing
  • Don't be afraid to question (technical) decisions
  • Focus on connecting with people (over immediate goals) and reap the deep rewards
  • Understand where the business is headed, or at least what it prioritizes, and align or get out


tl;dr (lessons learned)

  • Just because you're excited by a technology doesn't mean you are actually passionate about it
  • Partnerships with no investment can quickly feel imbalanced
  • Hobbyist involvement is nice, but nothing to count on

AWS Professional Services

tl;dr (lessons learned)

  • Large organizations are always going to favor patterns and convention over doing things the most practical way
  • Don't stress about the work; just try to applying yourself and your focus to it at the best pace you can

Made with 🧠 and 🫀 by Joshua