Turn Boring Discipline Into Massive Freedom

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Do you want ultimate freedom? Do you ache for the ability to leave on a moments notice, hop on a jet, and fly around the world? Have you ever wanted to date high-value men or women? Do you struggle in a corporate role as you wish to start your own business? Have you ever hoped you could design 100% of your life, to your exact vision and specifications?

Me too. What if I told you that you could achieve all of these freedoms - right now - and that the linchpin was discipline?

Discipline. Yawn. Discipline is something for military vets and the children of Mary Poppins, am I right? It’s for CEO robots who don’t have a life and dedicate their time to the cause of a corporation. Can I get a “hell yeah”?

Well, save your breath, because it’s wrong, it’s all wrong. We’ve been fooling ourselves for years, thinking that discipline was reserved for sticks in the mud - people who don’t grab life by the horns and instead give their time and attention to “the man.”

Here, to make it easier to conceptualize, let’s think about someone on the opposite end of the spectrum. I envision a “free spirit” as someone who embodies Carpe Diem. The type of person who you meet in hostels or couch surfing across Europe. A person who sees life for what it really is and understands that we’re all going to die, so we might as well have a damn good time here while we can. Who do you see?

But boy did I have it wrong, and if you agree with everything up to this point, I’ll let you in on a little secret: you’re incorrect, my friend.

Try this equation on for size: Discipline = Freedom

I first heard these words spoken by Jocko Willink, Navy Seal, corporate consultant, and nonfiction self-help author. Hm, fits the bill of someone who would have discipline, right? Also, someone who you might not see bunking in a 12-bed hostel room, which, for some odd reason, is my misguided criteria for someone who “gets life.” Now, I’ve never met the man, so I'll say explicitly that I don't know, but I can also say with 100% belief and conviction: Wrong, wrong, wrong. Turns out that Willink has more freedom than even the most transient world-traveler, and it’s all because of discipline.

Discipline in the Minutia Allows for Freedom

I’ll be honest with you, even after everything I said, I still think of freedom as the option travel at a moments notice. I guess in a way, that really is freedom: the ability to pick up and change your schedule at the drop of a hat. But you see, these grandiose plans to seize the moment can only really happen if you have discipline in the day-to-day. Let me explain with an anecdotal story of my own:

I’m writing this from Austin. But no, I don’t live here. Well, not technically. I still call San Francisco home, and in fact, I still have an apartment waiting for me when I return. However, I’ll be staying in Texas for the entire month of June, and maybe longer. I rented a 1-bedroom Airbnb, converted it into a satellite office and makeshift home, and have been immersing myself in Austin culture ever since.

Now, the ability to leave my home and move to another state for the month is a pretty freeing experience. I’ve literally had a brand new experience every day, I've met new and interesting people, and I've consistently melted from the heat (my pale, San Francisco skin wasn’t ready for the hot Texas sun).

To me, having the freedom to do something like this is the ultimate. It’s what I’ve worked for…for a long time. Longer than I’m embarrassed to admit.

But, the only way I was able to give myself this level of freedom was through strict discipline. You see, I make money online, both with my company, as well as through various "side-gig” clients, who I help with email / content marketing. And that’s where the discipline comes in. When I was still shackled to my corporate chains, I needed to find a way to generate income without going out and getting another 9-5 job. So, while I held my “normal job,” I worked mornings, evenings, and weekends to find ways to earn money outside of a paycheck.

I effectively worked an additional 20 hours a week, if not more, to make it happen. But, I did make it happen. Now, it wasn’t as easy as “I wanted it, so then I did it,” but I only have so much white space on this blog article, and I need to get to the point. Just know that it was hard work, juggling a side gig and a full-time job. You guessed it, it took discipline.

And then, once I was comfortable with the side income I was making, I left my job and jumped full time into entrepreneurship / freelancing / consulting. The combination of my three income streams was able to cover my costs of living while I worked to grow each stream of income - with the goal of fully replacing my six-figure corporate salary. And that’s where the second element of discipline comes in.

You see, once I was out of the corporate environment, and working strictly with a few key business partners and clients, there was no one telling me to work. I was 100% in control of  my own income, which means I was 100% responsible for my own motivation. While the goal is never to trade time for money, in the beginning, you almost always have to. And often, in the beginning, the proportion of time you work versus the amount of money you actually earn is skewed toward working hours and not toward income. So, it takes incredible self-discipline to wake yourself up every morning, open your computer, check your email, and tell yourself that you’re going to own the day.

Much easier to lay in bed. Trust me.

But, the results are twofold: One, I now know I can be self-sustaining, and even if I return to a corporate environment, I’ll always have the ability to generate my own income again, which is a freeing through. And two, since I can work remote whenever I want, from wherever I want, I have the freedom to travel. Anywhere, as long as there’s internet connection.

Be Careful About the Freedom You Want

Sounds great, right? Not so fast, there’s always a caveat, and the grass is always greener on the other side.

You see, while I have ultimate freedom in my location-independence, I’m still trading time for money, which means that it’s hard to take a day off. Even my digital advertising agency, which will eventually become passive income, requires dedicated time and effort on the front-end to get it to the point of passivity on the back-end. And of course, consulting work is almost always hours for dollars.

So, when can I take a vacation? No, seriously, I’m asking you, because I haven’t yet figured out a way. Now, I’ve only been doing this full-time for about 8-months or so, and there’s a long way to go, but it’s important to point out that it’s not all roses and dandelions. Sometimes, the freedom you seek is actually a box that you trap yourself in.

Which means the discipline needed to gain freedom really never ends. Because even now, working from an Airbnb in Austin, I’m still moving toward the holy grail of passive income. It’s going to take dedicated discipline over the long-term to achieve. But, my assumption is the rewards on the back-end will be worth the intense, daily focus needed to get there.

So my advice to you is this: If you want freedom, in whatever capacity that means to you, go for it! There’s no harm in trying. In fact, there’s more harm in not trying, since you’ll always wonder “what if.” But be wary and alert of the changes to your schedule and your mental outlook. The last thing you want to become is the business owner who grinds out 80-hour work weeks to avoid the 40-hour work week.

Doesn’t sound like much freedom to me. However, maybe 80-hour weeks is what’s needed to eventually have 4-hour weeks. The only way to find out is to test your assumptions, learn from your mistakes, and iterate on your goals, dreams, and the ultimate vision of your life.

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