Top 10 Gen Y Blogs — Archive (2008–2010)
From 2008 to 2010, I published a recurring “Top 10 Gen Y Blogs” series.
Every other month, readers voted, communities rallied, and new voices broke through. The lists weren’t perfect (some called them popularity contests), but they were lively snapshots of a time when blogging was the dominant medium for Millennial voices.
This page serves as the permanent archive of those editions. While the original posts have been consolidated, the summaries below capture the highlights.
2008
October 2008 — The Inaugural List
The first list grew out of my internship with Seth Godin, early Brazen Careerist conversations, and a Squidoo page where nominations and criteria lived.
Personal Branding Blog debuted at #1, with Employee Evolution and Ben Casnocha close behind. Newcomers like Hard Knox Life and Driven Leaders signaled the wide range of Gen Y voices starting to emerge.
2009
January 2009 — New Year’s Ballot
Not a finished list, but a turning point. Instead of curating the rankings myself, I opened it to community voting. With 36 comments and tons of energy, this ballot proved the series had outgrown one person’s judgment and worked best when the crowd got involved.
February 2009 — First Community Vote
Readers picked the winners, and The Mad Grad took the #1 spot, dethroning Personal Branding Blog. Employee Evolution and Work.Love.Life held strong, while blogs like Modite and Politicoholic broke through.
April 2009 — Politicoholic Rises
A major shake-up: Politicoholic surged from #7 to #1, thanks to Nisha Chittal’s prolific political and social commentary. The Mad Grad slipped, Personal Branding Blog held steady, and newcomers like Modite and Twenty Set reflected the diversity of Gen Y blogging—from careers to politics to raw personal storytelling.
June 2009 — Life Without Pants Debuts at #1
The most ballots yet. Life Without Pants stormed into the top spot with its community-driven style, while Small Hands, Big Ideas debuted at #2. Modite continued its climb, Politicoholic held strong, and familiar names like The Mad Grad and Employee Evolution rounded out the list.
August 2009 — Life Without Pants Stays on Top
This month brought the highest number of ballots yet and plenty of new faces. Life Without Pants held #1, while Small Hands, Big Ideas stayed at #2. Newcomers like Owl Sparks and Location 180 shook things up, alongside returning favorites like Life After College and The Rest is Still Unwritten.
October 2009 — A Three-Way Tie for #1
Over 35 ballots made this one of the most competitive lists yet. For the first (and only) time, the top spot ended in a three-way tie: Life Without Pants, Location 180, and my own Ryan Stephens Marketing. Life After College continued its steady rise, while Exile Lifestyle and Thrilling Heroics added a location-independent, adventurous flavor.
December 2009 — The Final List
The series closed with one last shake-up: Jenny Blake’s Life After College finally claimed #1, capping her steady rise throughout the year. Life Without Pants slipped to #3 after a dominant run, while newcomers like Sydney: Unfiltered and OwlSparks made strong showings. The mix highlighted how far the community had come—career tips, raw essays, and unconventional life experiments all finding an audience.
Debates & Commentary
By early 2010, the lists had sparked hundreds of comments and inspired spinoffs. Posts like The Problem with the Top 10 Gen Y List and In Defense of Voting for Top Gen Y Blogs captured the growing tension between recognition and popularity contests.
At their best, the lists gave young writers exposure and momentum. Many went on to bigger platforms, books, and speaking careers—proof that the Gen Y blogosphere was a launching pad.
Closing Reflection
The Top 10 Gen Y Blogs series was messy, fun, and very much a product of its time. Looking back, it’s a reminder of how community-driven blogging was in the late 2000s—before Twitter threads, podcasts, and Substack newsletters took center stage.
For more reflections on what these lists meant, see:
👉 The Rise of Gen Y Blogs (2008–2010): A Retrospective
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