I Quit My Job and Started My Own Business, Taoist Style

Source: http://riverbankoftruth.com/2013/09/08/the-tao-of-pooh-by-benjamin-hoff/

After I read the 4-Hour Work Week, starting a “muse,” an online business that generates enough passive income to sustain my ideal lifestyle, seemed like the ultimate way to live a happy life. I wouldn’t have a boss and I would only spent a minimal amount of time on tedious tasks. I could spend my days lounging and reading and traveling. Basically, a dream come true.

My first attempt at an online business, TrekDek, was based on the idea that travel can be an important personal development tool, if done correctly. This business has not been successful. Since I started it in 2011, I think I’ve probably lost a few thousands of dollars overall and I spent a bunch of time on it.

I don’t regret starting it. It was fun, and I picked up some useful skills and met some interesting people as a result. But it was hard. Starting a company with no relevant experience and with a brand new product was very difficult and frustrating.

This is to be expected. Indeed, the current start-up/entrepreneurial wisdom teaches that start-ups are supposed to be hard, and that you are likely to fail. But if you succeed, you could be rich and successful beyond your wildest dreams.

We romanticize this idea of going against the grain, forging ahead despite the dismal odds of success.

The famous “Man in the Arena” quote by Teddy Roosevelt nicely encapsulates American’s attitude toward entrepreneurship and risky endeavors in general:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat. 

I just got chills reading that.

But let’s look at the Taoist approach to success, the judicious application of wu-wei, or non-action.

In the pursuit of learning, every day something is acquired.

In the pursuit of Tao, every day something is dropped.

Less and less is done

Until non-action is achieved.

When nothing is done, nothing is left undone.

The world is ruled by letting things take their course.

It cannot be ruled by interfering.

Chapter 48, Tao Te Ching

Letting things take their course….how antithetical is this compared to the entrepreneurial mindset of “innovation” and “disruption.” To be an entrepreneur in the American mindset is to force change to happen.

A Taoist would say perhaps that the reason entrepreneurship is so difficult is because entrepreneurs are trying to work against the Tao, work against the natural way of the universe.

Now, I just made an important change in my working life. I have decided to quit my job to start my own business, and I already have tens of thousands of dollars in revenue lined up for the next few months.

Unlike TrekDek, where I lost a few thousand dollars over the past few years and worked much harder to achieve that negative result, my new business was very easy to start.

What exactly am I doing?

I will become an independent contractor to my current company, doing the same thing I am doing now, for twice the pay.

Here’s what happened to allow me to make this change

I did my job

If I am being honest, I was not a great employee. I wasn’t terrible, but I wasn’t great either. Some things I did well and some things I did poorly. When a particular task interested me, I put in more time and energy into it. When a task bored me, I spent as little time on it as possible.

I didn’t force myself to develop new skills or play politics or do anything that felt unnatural. Well, that’s not exactly true, being an employee feels unnatural to me, so not quitting took some will power and force. But overall, I worked in a way that suited me.

Fate placed me in fortuitous circumstances

Last fall, one of my co-workers left and I took her place on a project that required people with security clearances. I was not happy with this change initially, as I had to work at the client site most of the week, but the pace of work was slower and the tasks were more to my liking.

The client liked the work I was doing and told my managers so they were happy. When it came time to add more money to our contract, the client wanted to have me stay on the project. So I had to tke the position and move cities, I found affordable movers and that was it!

This came at time when I was basically the only person available to do the work. My company didn’t have other people with security clearances they could send, so I now had some leverage with my company.

I seized an opportunity

Because I had leverage with my company, I used this to get what I want. My company routinely works with sub-contractors, many of whom are former employees.

After thinking through the risks of leaving my company to become an independent contractor, I pitched it to my managers. One of them pushed back a little, but not too much, and I pushed back a little.

Finally, we came to an arrangement where both my company and myself get what we want. They get someone competent to do the work, and I get more money and independence.

Overall, this transition, felt very easy and very natural. No, it’s not passive income and I’m not making millions of dollars. The work is pretty much the same as it was before and it’s still somewhat dull. But the psychology of it is very different. It feels right.

Takeaway – The Pooh Way

I’m not quite ready to say that we should ditch the man in the arena entrepreneurial model. There is something romantic and inspiring about going out on your own to pursue a crazy idea that is likely doomed to failure.

But I also think there is room for a Taoist approach, one in which you make entrepreneurial moves based on concrete opportunities that present themselves to you. Perhaps we should call this the “passive opportunism” approach to entrepreneurship. We don’t to try brazenly force success to happen, but rather, take small actions and keep our eyes open to favorable situations.

There is a great example of wu-wei in the book, The Tao of Pooh, that the author describes as the “Pooh Way.” Pooh, by the way, is Winnie the Pooh. In one particular vignette, Pooh and the gang are looking for Small, a very small beetle. The group searches and searches to no avail. Pooh, of course, falls down a well on top of Piglet. Piglet, after pointing out that Pooh is sitting on him, excitedly points out that Small is crawling on Pooh’s back.

It was only when Pooh and Piglet were distracted by something else (being stuck in the well) did they end up finding Small. They achieved the goal through non-action.

The author describes the Pooh Way like this:

“Those who do things by the Pooh Way find this sort of thing happening to them all the time. It’s hard to explain, except by example, but it works. Things just happen in the right way, at the right time. At least they do when you let them, when you work with circumstances instead of saying, ‘This isn’t supposed to be happening this way,’ and trying hard to make it happen some other way. If you’re in tune with The Way Things Work, they work the way they need to, no matter what you may think about it at the time. Later on, you can look back and say, ‘Oh, now I understand. That had to happen so that those could happen, and those had to happen in order for this to happen…’ Then you realize that even if you’d tried to make it all turn out perfectly, you couldn’t have done better, and if you’d really tried you would have made a mess of the whole thing.”

So is it better to be The Man in the Arena or Pooh? Based on the way things played out for me, it’s better to be Pooh. But perhaps I wouldn’t have become Pooh without first trying to be The Man in the Arena.

Regardless, I think I’m going to try this whole wu-wei thing a bit longer and see what happens.

  • Magicub

    Have you read Brene Brown’s “Daring Greatly” titled with this Man in the Arena on mind? How is the business going so far?

    • I haven’t read her book. What are some of the highlights?

      Business is going well so far. Had a somewhat unexpected month off, but I’ll have work through the end of the year, making my previous annual salary in 6 months. So, overall, very excellent.

      • Magicub

        The book mostly proposes that we are living in a shame-prone culture and that shame should not be used to correct behaviors, and behave less like the critic and more like the man im the arena but not in the way of ignore your shortcomings rather than embrace vulnerability. Now that you are on your own, Is there something that you miss of your old workplace?

        • Interesting. I actually think shame is quite useful, and that American culture at least has been moving away from it. It seems like we want to use the law to correct behaviors, rather than individual and social shaming, which I think is…a shame. I guess the takeaway is one should be ashamed of doing things that are truly shameful.

          I’m actually a sub-contractor for my previous company so I still get to interact with my former colleagues and such. I don’t really miss it all that much, though now I’m missing some opportunities to practice Stoic thinking 😉

          • MarcHamann

            Have you ever been on Twitter? Social shaming is thriving…

            Brene Brown is more interested in our attitude towards ourselves rather than our attitude towards others.

          • The twitter/internet shaming thing is interesting. In some ways I like it (usually when I agree with the shamers) but when I see it happening it mostly seems to be shaming things people have said/done without understanding the context and then blowing it way out of proportion. I think shame at a community level is more helpful because you are somewhat vested in the success of the people in that community.

            On the individual level, I like the Christian perspective that say human nature is fundamentally broken. It is a sort of equalizer that allows us to strive towards being better while also acknowledging that we will always fall short in some way.

  • Kevin

    I’m contemplating a similar thing at work, so this gives me hope. I take it you have a little more control over your hours as well? I’ve been hesitant to pitch it to them as I think it would result it a net negative money wise for me but “buying back” some of my time might be worth it.

    • Yes, I have more control. I don’t work Fridays anymore (mostly). I would just make sure you have enough leverage to pull this off successfully. If you’re fairly uncertain about the outcome, I would hold off. If you’re certain about the outcome but are just nervous, then you should go for it.

  • MarcHamann

    One of the weaknesses of the Tao of Pooh is that it presents a very oppositional take on Taoism that I think often misses the point.

    The Man in the Arena can work with the Tao or against it. He can cluelessly defy the bedrock of reality and certainly fail, or he can merely ignore the fake limitations imposed on him by those who think you can resist the change and risk inherent in the world.

    The dope smoking hippie lounging in his basement is not necessarily a Taoist. The vigorous achiever always on the move is not necessarily out of step with the Tao.

    You must perceive the flow of things before you can move with them or against them, and everything that flourishes is part of the flow of things.

    • Good point; I agree. I think he was trying to contrast it with western thinking though which seems to only think in terms of man in the arena.

      However, like you say, knowing how to switch back and forth is the real test.

  • Daniel Verdugo Nosov

    Congratulations, Dale. I’ve been following you since your Hinduism days, and I noticed, that you really want to become self-employed. Now, it seems, this whole ancient wisdom thing worked out for you.

    • Thanks Daniel. It has been a good move so far. Of course, I try to practice negative visualization so that I’m psychologically prepared in case something goes wrong.

      • Daniel Verdugo Nosov

        I read somewhere, that one should implement negative visualization _especially_ in the days he expierences something what he percieves as good.

        So, as Seneca whishes in the end of his letters, “vale”. (-: