Makes my blood boil

I made a list the other day of things about being self-employed that have made me angry at various points in the past:

    1. Not having much control over my income, and feeling like I’m working super hard but just scraping by financially
    2. Unreasonable requests from clients
    3. A previous business partner
    4. Feeling out of control over when new business showed up
    5. Unreasonable deadlines

I’m not a lot of fun to be around when I’m angry. 🙂

I’m one of those people that gets withdrawn and sullen when angry, and I’m a master of the passive-aggressive basket of tricks.

I’ve worked on improving how I deal with anger, and I’ve also worked on improving the things that make me angry in the first place.

It might not help you, but in case it does here’s what I did to change the things that made me angry.

Not having much control over my income, and feeling like I’m working super hard but just scraping by financially

I specialized (and wrote a book about how self-employed software developers can do the same). People now pay me $300/hr and thank me for the opportunity to do so.

No, that doesn’t mean my income is $300 x 4h per day x 5d per week x 50w per year = $300,000/yr. I’ve chosen to work less (3d/week in the office) and grow my business more slowly. I also do “unpaid” work all the time knowing that it will help build assets that generate a financial return slowly over the long term.

RE: growing slowly, I’m averse to certain things that can make business models like mine grow more quickly. Those things are: lying, over-promising, affiliate sales, big advertising spend, and the launch/abandon/launch some more cycle, to name a few. My aversion to those things has made growth a more slow and gradual process for me.

Selected Resources:

    • A book called Blue Ocean Strategy:
    • A book called The Win Without Pitching Manifesto:

Unreasonable requests from clients

I did two things here. One was to build and start selling a product so I wasn’t 100% reliant on revenue from client work. That automatically made even unreasonable client requests less anger-inducing.

The other change was to learn to ask why. This is something that needs to happen continuously: during the sales conversation, during the diagnostic phase of the project, during the delivery of the project, and during any followup support phase.

Incidentally, unreasonable requests from clients decline in direct proportion to your perceived status as an expert. Specialization contributes to perceived expert status.

For me, it was always easiest to say no to a client request if the “no” is said with their genuine best interest in mind. I have two resources that will help with that:

Selected Resources:

    1. A book called No: The Only Negotiating System You Need for Work and Home: (get the paper version of this book. The Kindle version of a similarly-titled book from the same author is inferior.)


  1. (I’m a relentless promoter of Jonathan Stark’s work because he does the best job I’ve seen of teaching self-employed software developers how to ask why during a sales conversation.)

A previous business partner

This is not 100% my story to tell, so I won’t share details here. TL;DR: I learned a lot!

Feeling out of control over when new business showed up.

The core problem here was having no repeatable, sustainable lead generation practice. I say “practice” because the idea of a lead generation “system” that somehow runs on autopilot is a false dream. Effective lead generation for expertise-based services business take honest to goodness work done over a long period of time (6 months minimum in my experience). Of course you can systematize that work, but you still have to show up and do the work. So I call it a practice rather than a system. Might just be a semantic difference, but to me it’s a significant one.

Anyway, a lead generation problem is almost always a positioning problem first and a lead-gen problem second.

Making a good decision about how to specialize and following through on that decision with consistent discipline eventually solves the positioning problem. But what about solving the lead generation problem?

I chose three things from and do them as consistently as I can. My preferred tools are podcast guesting, pumping value into my own email list, and guest posting (in that order).

Selected Resources




Unreasonable deadlines

Almost every time this was caused by a combination of my poor estimating ability and procrastination. TBH, I have not improved these things at all.

Rather than improving my estimating ability I just increased my level of skepticism in my own estimates. Working fewer days per week has helped some with the procrastination.

Selected Resources

  • I got nothin’ for you here. I’d rather increase the value I create than find ways to get more done in less time. The former feels like I’m serving my audience better, while the latter feels like speeding up an assembly line. I guess the one thing I’ll add is that having a sense of mission is very helpful in every aspect of an expertise-based business, including productivity.

Again, I don’t know if these ideas and resources will help you with whatever makes you angry about your business, but I certainly hope they do.

Your thoughts?


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