There are people you come across in life that are able to create authentic & true-to-life illustrations, and that are able to put into words the struggle you’ve been experiencing the bulk of your adult life. For me, Steven Pressfield is one such person.

I recently came across Pressfield’s work as I was reading Seth Godin laude the praises of this amazingly gifted author. I agree with Seth; Steven Pressfield has authored books that have helped me in many ways. What’s more, I’m saving a lot of money I was spending on therapy–(results may vary.)


I want to learn why certain pursuits of passion work and others end up falling flat. Why do some people succeed and others fail? I feel this question has become trite. There are a metric crap-ton of bloggers/writers/podcasters who have asked this question. Yet, one needs to take a step back and ask another question: Why do we all end up asking this question over and over? Could it be that the question has not been answered as of yet–at least satisfactorily? Or has this particular question become a wonderful, simple way to elicit online search traffic?

I am not jabbing my fellow thought leaders. I am only interested in establishing a compelling comparison. Am I simply adding to the noise surrounding the ‘follow your passion’ humdrum that pervades the online space? Or can I contribute to it in such a way that it helps at least one person work through their own foibles.

At ExecutingPassion, I am working on codifying the process of the personal transformation that has to take place as someone moves from employment into entrepreneurship. In Turning Pro, Steven Pressfield argues that there is inevitably a personal transformation when one leaves the relative immaturity of being an amateur and turns pro. Steven likens it to growing up and becoming an adult. Funny thing is my buddy Alan Sangma said the same thing about becoming an entrepreneur.

Three Things Steven Pressfield Taught Me


When I am feeling like I don’t possess anything that someone else would value, I instantly get depressed. This feeling leaves me powerless to produce anything at all. I feel like I can’t even do it for myself because I can’t muster the energy to move beyond the notion that I feel like I suck, so ‘what’s the point?’.

• Tip

Stop and ask yourself, “…does this fear, rage, anger, etc. really exist outside of my mind?” Often times what I notice is that if I take a moment to realize that this simply a feeling I am having at this particular point, the feeling dissipates. Five minutes later, I’m almost a new person.


I work as an instructional media production engineer. It involves some elements of creatively solving problems for faculty. Yet, it is a ‘shadow career’ of what I could be doing. This is a concept that Pressfield talks about in Turning Pro. I want to make sure that when I feel like dog poo I, as quickly as possible find a way, any way, to solve a problem for someone else.

• Tip

By shipping value regardless of how you ‘feel’, you grow closer to being a professional, and closer to being an entrepreneur. I think you’ll find, like I do, that you can quickly regain your vision, direction, & footing.


When I eat something that I know does not have a shred of nutritional value, I feel guilty. I feel like I let myself down. I feel like am sabotaging myself for no logical reason at all. I think in some varied ways we all exhibit this issue.

We have an ideal Self in our imaginations. Angelina Jolie & Kate Beckinsale do not hide their lust for this Self. This Self is a New York Times Bestselling Author. This Self stopped a bar fight with a witty joke. This Self sang the national anthem…of the world. This Self saved babies from a burning building, then demurred when the TV news reporters sought them for an interview for their heroic valor. This Self is the most interesting person in the world.

• Tip

Give yourself a break. I do not mean make excuses as a rule. I mean understand that you are not going to be perfect. You are not going to build a perfect single-person enterprise. You are not going to be immune to customers from hell. It’s going to happen. You are going to jack up. At times you are going to suck. You need to be ok with sucking on occasion. It doesn’t mean that you are going to suck forevermore.

My Favorite Steven Pressfield Books

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