Jay Shepherd

jay shepherd headshotJayShep.com
+01 617.213.0067

Email Jay
Twitter @jayshep

Jay Shepherd is obsessed with two things: (1) simplifying business ideas, and (2) toast. Unfortunately, though, the making of toast is beyond the scope of this blog. Which is too bad, because he really has it down to a science.

When not making excellent toast, Jay works as a writer and speaker focused on simplifying business ideas. He’s a member of the growing breed of creatures known as “recovering lawyers,” who resemble regular lawyers except that they smile more.

Before his recovery from lawyerhood, he enjoyed helping companies and managers stay out of trouble. This experience with businesses of all types and sizes helped him come to see things differently. He saw too many lawsuits and business disasters that could have been avoided with clearer communication and simpler approaches. This fueled his obsession with simplifying business ideas.

Simplifying is at the core of his new book, Firing at Will: A Manager’s Guide (Apress, 2011), an unlawyerly handbook for the riskiest thing you can do at work with your clothes on: firing employees. (It actually has a lot to do how to fix your workplace so that you don’t have to fire people.) His forthcoming book, The Cure for Work: Six Simple Remedies That Free Us to Do Our Best Work, promises to be even more upbeat. And more simple.

Jay also writes some blogs: this one, which you probably already figured out; Gruntled Employees, which is all about workplace happiness; and his professional-services blog, “The Client Revolution.”

Before he hung up his lawyer spurs (no, that’s a real thing), Law and Politics magazine named him one of the Top 100 Lawyers in New England. Which was nice, although video footage from the award-show after-party has been locked away as evidence.

Because tracking time is a demeaning activity, and of no importance to his clients, Jay banned timesheets from his Boston law firm, Shepherd Law Group. Without timesheets, lawyers have to learn better ways of pricing, so he did. Later, Jay opened Prefix, LLC, to help other professionals learn how to price their knowledge. Jay’s also a senior fellow at the VeraSage Institute, a think tank (or fringe group; tomato, to-mah-to) that believes that the lives of professionals shouldn’t have to suck.

For something that looks more like a résumé, you can check out Jay’s LinkedIn page. And for pithier messages, follow Jay on Twitter at @jayshep.


  1. […] Shepherd is a Senior Fellow at the VeraSage Institute and a recovery attorney. He operated Shepherd Law Group for a 15 years, […]