Leveraging Holistic Synergies

Educational Resources for Consultants, Solopreneurs, and Freelancers

NOTE: Very much in progress but published by request as its still moderately useful.

I've organized this primarily by media type, but it might be useful to create a cross-listing by areas of focus. Let me know what you think by tooting at me on the Twootstroms: @bennylope.


Let's get this out of the way: most business books are bad. Like, really bad. These books, not all business books, are not bad. They're not perfect, but they're each sufficiently useful in their own way.

Flawless Consulting

Million Dollar Consulting

A bit on the breezy side, stylistically, but a 'classic' if such a thing exists, for independent consultants. That's one thing that's particular to the author and the intended audience: this is geared toward independent consultants. That is there's a presumption of consulting and further of doing so indepdently. That does not mean not working with other people, or, as works for me, actually having a business partner, but the advice here is not all that useful if you're a consultant in a larger firm or work for someone else - clients notwithstanding.

The Positioning Manual

Hourly Billing is Nuts

Design Is A Job

Fuck you, pay me. [Mike Monteiro]

This is a book for designers. It's also for people who aren't designers. If you work with (partner with) designers or do anything vaguely creative - which includes software development - this is worth a read.

This book is a guide to making a living as a designer. It contains the fundamentals of being a working designer, including working with clients and others, valuing your work, and getting paid. This book will look at ways to communicate and apply these fundamentals to every aspect of your job. The goal is to expand your view of your job as a designer to include not just your talent, but the business and communication aspects as well.

Independent Consulting Manual

Lean Customer Development

Little Red Schoolhouse

You write emails and documents to your clients and consisently fail to get the responses - and results - that you'd like. This is because you're writing for you and you're not motiviating the problem for your client, the cost of the problem to your client, how you'll solve the problem for your client, and the benefits to your client of your proposed solution. If you keep writing like this you're going to continue on your hamster wheel of frustration. Instead, try reworking your writing along these suggested lines and over time you'll start to see radically different responses from your clients that result in improved outcomes for them, and a better freelancing business for you.

Notice what I did there?

Don't think you can find this book on Amazon. This is compendium of handouts and worksheets from a college writing curriculum called, you guessed it, the Little Red Schoolhouse. Originally developed in the English department at the University of Chicago, I had the pleasure of taking an upper level writing course taught by Greg Colomb and Jon D'Errico at the University of Virginia based on Colomb's experience teaching at Chicago. You'd be hard pressed to find a better guide to effective writing.

Man's Search for Meaning

Another non-business book. A two part book including Viktor Frankl's personal account of surviving life in Nazi concentration camps and finding meaning in deprevation and amid the loss of everything you hold dear (Frankl lost almost his entire family, including his wife). The second part of the book is an extension of the memoir, in which as a psychiatrist he outlines his existential philosophy of analysis, called logotherapy. I first read this book at a low point in my personal and early 'professional' life - the timing was coincidental - and its both a sad and inspiring story. Striking out on your own is an amazingly freeing experience, but we often fail to recognize the responsibilities and weight that come with freedom until we're at a point so low it looks like there's no way out.

I'll [badly] paraphrase an anecote I loosely recall from the book to coarsely illustrate the philosophy:

Patient: Dr. Frankl, my life is terrible, I wake up daily and think about killing myself.

Frankl: What's stopping you?

Patient: ?

Frankl: Why don't you kill yourself?

Patient: If I did that my children would be left alone without their mother, my grandchildren would never have an opportunity to know their grandmother...

Frankl: You don't need my help. Go see your grandchildren.

The point is not to contrast your superficial "first world" struggles with that of life in Auschwitz ("You got it so great kid!") but to remind yourself that you have both freedom and responsibility for how you face the world and the meaning you find, and make in it. It's a cold dip in the ocean compared to the milquetoast inspirational quotes your friends like to share on Facebook.


The Freelancer's Show

The Freelancer's Show is hands down my favorite 'freelancing' related podcast. I'm using three main criteria:

  1. Useful and applicable information
  2. Engaging topics and speakers (hosts and guests)
  3. Easy to listen to (technical issues, quality, etc).

This podcast is geared toward freelance developers so may be less relevant to people working in other disciplines. The hosts include a regular circle who bring different experiences, both technical and business. Whether they have a guest or not you get different perspectives even when everyone's in agreement.

Good for strategic and tactical advice, as well as being a great outlet to feel like you're not struggling through a problem on your own.

Selected episode: Giving Advice Away For Free

Making Money Online

You may not like this podcast. And that's okay. The hosts, they won't care. It took me a little while to warm up to to it. It's weird. But I like weird things, so here we are. Nick swears a lot. I like swearing. Unless you're Samuel L Jackson you probably can't get away with saying 'fuck' in every sentence and not sounding like an asshole though. Salty language is just that, salt that helps flavor our prose, and like salt there's an optimal quantity before it overwhelms the total flavor of the dish. Whatever. It is a good podcast though, really.

The hosts, Kai and Nick, are both independent consultants and the episodes range over topics related to life as a freelancer, er, independent consultant, and the business of running your own consulting business.

Selected episode: How You Signify To People What You Do

(Note: in one otherwise helpful episode Nick yells at you that you must necessarily be on W2 payroll to secure a home mortgage; we know that if the existential quantifier is true then the universal quantifier for the inverse must be false, ergo this is not necessarily true. It is certainly easier to secure a mortage with W2 statements but any lender is going to know that its still your business. Further if you're paying yourself on payroll then you'd better be doing that because you're filing as an S corp in which case unless you're truly a million dollar consultant you're likely not paying yourself in salary toward the upper end of the pay scale, if you know what I mean, so the dollar value of your W2 payments won't be that high.)

Stacking The Bricks

Tropical MBA

The Tropical MBA is a hit or miss podcast if you're looking for material relevant to freelancing. Its core audience is location independent entrepreneurs building product businesses (e.g. working from a beach in Southeast Asia selling cat condos on the Internet). That said there's a reasonable degree of overlap if you pick your episodes, and it's one of the best produced podcasts I've listened to. That sounds like such a superficial compliment but there's a small joy in hearing the back and forth move smoothly like a practiced ballet.

The selected episode won't teach you how to get better clients, sorry. It's just a terribly good episode ranging over various topics with an interesting thinker.

Selected episode: A Conversation With Ribbonfarm's Venkat Rao

Kalzumeus Software

An infrequent podcast and one only incidentally related to freelancing. This is patio11's podcast, or Patrick McKenzie if you prefer. The podcast is primarily geared toward an audience of software developers and solo founders but a great deal of the content (customer onboarding, balancing business and family) is pertinent to the independent consultant and freelancer.

Selected episode: Teaching As Marketing

Double Your Freelancing Podcast

Freelance Transformation

Ditching Hourly

The Three Month Vacation

The Businessology Show


Bizcraft is, as best I can tell, d-e-d dead, but for a while it was one of my favorite business podcasts. The setup is Carl Smith of nGen Works and Gene Crawford of Period Three discussing various aspects of running agencies, usually over beers. I'm not sure how early in the day they started recording.

Selected episode: Next Steps, Working Too Hard & Time

Originally published 2017-01-30