4 Painful Lessons From an Agile Entrepreneur | Jesse Fewell 4 Painful Lessons From an Agile Entrepreneur – Jesse Fewell

4 Painful Lessons From an Agile Entrepreneur

By March 29, 2015Blog


Many of you know that a little over a year ago I launched out as in independent Agile entrepreneur, trainer, and coach. Well, there’s good news and there’s bad news. The bad news is that I suffered some pain and mistakes in this first year. The good news is that I was able navigate through those issues, but only when I took a moment to pause, and then practice what I preach about Agile methods. Here are some of those lessons I learned the hard way.


Know your WHY

Any leader should always be able to answer “why should we do this project at all?”. A clear and compelling vision will serve as your decision filter for when times get tough. Leaving a stable income to go independent requires a clear reason for doing so. For me, it was about control.

  • Articulate your Mission – In 2013, my consulting work tallied 126 hotel nights away from family. That’s not terribly unusual for the premier coaching work I was doing. But, eventually, it began to take a toll on the quality of my work. Moreover, my discontent made me a rather unappealing employee. It was time to make a change about what I was doing and why.
  • Measure your Mission – When I went independent, I wanted to be empirical about my decisions. During the course of 2014, I started tracking revenue-versus-hotel-nights. This metric would tell me if I was on track to have less money or more travel, relative to 2013. If I was off track, the data could help me make course adjustments in real time.


If you don’t know how to measure progress on your mission, then you probably don’t know what your mission really is.


Establish a CADENCE

Consultants make money by selling time. The more of my time I sell, the more money I make. Naturally, to get a new practice going, I had to say “yes” to whatever work on whatever dates my clients were asking, and whatever opportunities came my way. Before long, I was running at an unsustainable pace.

To address this , I borrowed a page from productivity guru Michael Hyatt, and drafted my ideal week:

MON = Create content
FRI = Appointments

Now, of course there are exceptions when I’m at a conference, or I’m supporting a client’s week-long program kickoff. The point is to have a baseline. That baseline helps me make decisions about what to tell a client when they’re asking for more billable dates than I have open.

The Scrum framework uses Sprints. The Kanban method uses “Flow”. I used Hyatt’s “ideal week”. Whatever way you do it, healthy operations come from a stable cadence.



Normally, as a solo practice, I carry a ton of risk. My clients have all the money, all the leverage. So imagine my surprise when things went BETTER for me when I take MORE RISK into my client conversations.

  • Use Lightweight Contracts – I’m no lawyer, so I use LegalZoom contract templates as short as two pages. Rather than drill down into all the things I will demand of the big-bad-client, we keep things very simple: deliverable, date, dollars, done. In fact, I had two clients in my first year where there was literally NO contract in place before I invoiced them. Lightweight formality places more emphasis on the up front conversations and relationship building, which has built a huge amout of loyalty with my customers
  • Offer Provisions for Executive Discretion – Lightweight contracts allow the two parties to reserve the executive discretion to adjust details around as needed. I am stunned at how flexible my clients have been, when I tell them, “I’m sorry, I’m booked solid on Wednesdays for the next several weeks. Can we try a Tuesday instead?”. I’ve spent a couple decades as a consultant/contractor, and have never dared to invite a client to collaborate on how to solve MY date challenges. But once I started doing that last year, I was stunned at how that kind of honesty and transparency yields good will in the relationship.


Build a TEAM

Here’s an insight:

Nothing worth doing is doable by yourself.

When starting out on my own, I had no choice but to do everything myself. After a few short months, the work load became too much. I had to ask for help. But when you’re short on cash, you can’t hire help right away, so you ask whomever you can. For me, that took the shape of three things:

  • Family – My wife was huge help in the beginning with logistics and administration. But then my teenagers got into the mix, scanning or shredded paper forms for me. Heck, since this whole venture was about achieving a healthier balance for me and for us, it felt natural to ask them to be a part of it.
  • Affiliates – Literally all of my public seminars last year were hosted by affiliates and marketing partners. They took the risk and reward of filling seats for those seminars, and I got a flat training fee. Moreover, I was able to leverage their staff to handle some of back office tasks to deliver those seminars.   In the beginning of an independent venture, less revenue / less risk is better position of strength than more revenue / more risk.
  • Automation – Automation is a great way to scale your output without hiring headcount. Even with family and affiliates helping me out, I noticed I had became too busy traveling and consulting to get invoices out the door. Rather than hire, I used Expensify to automate tracking and categorizing receipts. Waveapps.com automated reminders to those clients who are past-due on invoices.

Granted, once I had some cash in the door, I could start paying for real help. But even when I started with nothing, I could find creative ways to mobilize a team around me.


Bottom Line

This last year has been a test of my convictions and my priorities. The only way I have been successful is by getting serious about my WHY, my CUSTOMER COLLABORATION, my CADENCE, and my TEAM.