Lessons Learned - A Blog Series

Lessons Learned



I get questions. Like

  • What's the biggest mistake you've made?
  • What's the toughest decision?
  • What's the most important lesson you learned ...?

So I've decided to create a blog series and answer these questions from the perspective of lessons I've learned over the years. It starts with my last "real" job and goes through the sale of my last managed IT service business. 

I hope all business owners, especially those new to IT consulting, will learn from my mistakes (and maybe from my wins). And, as always, I would love to have your feedback in the comments.

If you have specific questions that you think would fit in the series, please send them. I'll try to fit them in the series where they make the most sense.

This Page was created as an evolving index of the series, so you can find articles quickly.

Episode 1: My Backstory - The Very Short Version

Episode 2: What I Learned on My Last Real Job - the Technical Stuff

Episode 3: Management Lessons I Learned on My Last Real Job - and the Worst Boss Ever

Episode 4: The HP Way

Episode 5: EDI and the Best Boss Ever 

Episode 6: Easing into Break-Fix 

Episode 7: Common Sense Calculations - That are 100% Wrong 

Episode 8: The Absolute Truths about Backups!

Episode 9: Technicians Who Refuse to Learn

Episode 10: Doing Things The Right Way


Episode 11: Finding Sources for Hardware and Software

Episode 12: Regular Monthly Maintenance

Episode 14: Everything Comes Together

Episode 15: My Most Regretted Decision

Episode 16: I Learn the Beauty of Perpetual Contracts

Episode 17: Learning to Quote Profitable Jobs

Episode 18:  Jimmy the Phone Guy, the Saga Begins

Episode 19:  Personal Health Crisis Takes Center Stage

Episode 20:  Y2K, the Dot Com Bubble, and Opportunity Everywhere


Episode 21:  Trying to Get That First Employee, Take One

Episode 22: How "Relax Focus Succeed" was Born

Episode 23: Selling Programming - Pros and Cons

Episode 24:  The Worst (Technical) Mistake I Ever Made

Episode 25: Hiring a First Employee - Take Two

Episode 26: Hiring a Great Administrative Assistant

Episode 27: Karl Takes a Vacation

Episode 28: We Need An Office

Episode 29: Managing Distributor Relationships

Episode 30:  The Hiring Formula for Early Growth


Episode 31: Tax Filings and When to Outsource

Episode 32: Microsoft Used to Love Us

Episode 33:  Stop "Rolling Your Own"

Episode 34: Nothing is more important than testing backups

Episode 35: Salute to Harry Brelsford, Founder of the SMB IT Community!

Episode 36:  My First RMM - and a Hint of What's to Come

Episode 37: My First PSA - The Good, the Bad, and the Ugly

Episode 38 - Selling the Perfect Combo 

Episode 40 - Flat Fee Maintenance 


Episode 41 - Managed Services in a Month - How it all started

Episode 42 - Weeding Your Client Garden

Episode 43 - Five Users and Above? Ten?

Episode 44 - Finding Your Ideal Client

Episode 45 - Firing Clients  

Episode 46 - Create a Mature Hiring Process

Episode 47 -  Front Office and Admins Rule!

Episode 48 - Discovering the ASCII Community

Episode 49 -  Hiring the Wrong Person    - I Learn Not to Break My Own Process

Episode 50 -  Finding a Peer Group


Episode 51 -  Outsourced Help Desk Support

Episode 52 -  All Hail the Service Manager 

Episode 53 - Harsh Reality of Hardware Margins

Episode 54 - Building Machines vs. Buying

Episode 55 - Local Partners: User Groups Everywhere 

Episode 56 - Good Owners are Not Necessarily Good Managers 

Episode 57 - Combining Everyone's Best Habits


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You can also find all the posts in the series by searching for "Lessons Learned." Here's the link for that: https://blog.smallbizthoughts.com/search/label/Lessons%20Learned

Be sure to subscribe to this blog. Over on the right-side column, you'll see the Subscribe by Email link. Just remember to white list the first email you get. And if you filter, put them all into one folder so that you can find new installments.

:-)