Welcome. I am Stephen Boudreau, a man in pursuit of goodness as a way of life. This journal is a collection of observations and commentary related to that pursuit.

I am regrettably sarcastic, perpetually optimistic, and (allegedly) willing to change my mind.

Fair warning: I am a recovering know-it-some. Please forgive me when I lapse into old habits.


  • I’m a designer at heart—primarily focused on digital products and services.  I believe that good design provides clarity and understanding—and is ultimately an act of kindness. 
  • My greatest (professional) passion is growing people and teams around clarity of purpose, trust in each other, and—what I like to call—the magic of collaboration (1+1=11).
  • I’m currently VP of Brand and Community at Virtuous Software.
  • In 2003, I co-founded a web design agency named Ascendio, with my delightfully grumpy friend Chris. We operated Ascendio for nearly 20 years—helping mid-to-large scale nonprofits leverage the digital space to grow their impact. During that time—we cultivated a beautiful team, invested in meaningful relationships, created significant value for our clients, and (I like to think) made a little dent for good in the world.
  • In 2014, Chris and I introduced RaiseDonors to the world. RaiseDonors is an online fundraising platform that took our decades of experience with Ascendio as a service provider and provided a turnkey SaaS product solution.
  • In 2020, we sold RaiseDonors to Virtuous Software and joined the Virtuous team full-time—to continue our mission to help nonprofits increase generosity in the world.
  • The move to Virtuous prompted us to conclude our ~20-year iteration of what Ascendio was. But what the future holds for Ascendio, remains to be seen. ⚡ 


Away from work, you’ll find me basking in the glow of family and friends. Almost everything in my life is made better by my wife. And my beautiful sons are everything I never knew I always wanted. Between them all, my heart bursts with love.

I try to live my life according to a simple three-pronged outlook

  • Love your family
  • Love your friends
  • Do what’s in front of you

I didn’t always approach life this way.

And although so much of what I write on this blog sounds like I take myself way too seriously—those who know me best recognize I am most at home indulging in silliness, being over-dramatic, and engaging in inappropriate humor. 


Friday nights, Telecasters, Shelley’s spaghetti, audiobooks, Everton, Alaska, sunglasses, sweaters, Dumbledore, old buildings, technology, magic, The Lasso Way, beets, Uno, lists.


Being late, regret, me monsters, half-assing, dogmatism, toe-shoes, pranks, ricotta, people eating on podcasts, typos, captcha forms, complaining, the texas longhorns.


Creating music has long been a source of delight in my life. When I was a young man, I even dared to imagine a life where I shared music professionally. But alas, life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.

In my story, that meant keeping it as a beloved hobby and passion. The beauty of writing (or simply playing) music–especially with a group of friends—is an act of creation. Together, you experience something that—for better or worse—would not have otherwise existed. I find it surreal and sacred.

It’s real magic. 

Christmas Songs

For a decade, my wife and I composed and professionally recorded original Christmas songs. They are silly, heartwarming, and one day—we may do it again. 

But in the meantime… please enjoy.

These ten songs represent ten of the most enjoyable experiences of my life. 

Copyright ©2024 Stephen Boudreau.