The Perils of Time Freedom

“The man who has lived the most is not he who has counted the most years but he who has most felt life.”

—Jean-Jacques Rousseau

The average american male lives to about 78 years old (females live to 82). Assuming I can hit that mark, I’ve got a solid 51 years, or 18,615 days of jammin out here on Earth. 1/3rd of that time I’ll be drooling on my pillow, so I actually have 12,285 wakeful days…(That’s SO much sleeping!)

I don’t know about you, but knowing this information about my remaining days really lights a fire under my tukus…

It’s the reason why time is the most valuable asset humans have, and the problem is you can’t acquire more of it like you can with other resources like money.

The only thing you can do is acquire your existing time-stock BACK from other things that demand it, and these days, this is getting harder and harder to do.

It’s this fear of regret, of not making the most of this limited resource of life, that is at the core of the most successful and subsequently happy people I know.

The Cost of “Doing What You Want”

If you ask most people what it is they truly want in life, you’ll hear a lot of “to be able to do whatever I want, whenever I want, with whoever I want.” In other words: freedom of time.

I’m certainly no exception to the rule, and looking back I’ve probably made most decisions based on if I can satisfy that desire.

I am grateful for the time freedom I’ve been diligently working to shape into my own lifestyle.

I’m blessed for certain and don’t take it for granted, but I definitely traded in for some other things that are also valuable.

I believe everyone is capable of manifesting true freedom of time in their own lives, but with some consequences…Unfortunately, like everything in life, time freedom doesn’t come without some costs.

Here are a few ways I’ve learned to bring some time freedom into my reality, and some of the drawbacks you may face from life during its pursuit.

It’s up to you to decide how badly you want to take your precious time back and if you’re willing to endure some of the necessary perils of time freedom:

1. Learning to separate your time from your income

“Your income is determined by how many people you serve and how well you serve them”

The Law of Compensation from ‘The Go Giver’

If you truly desire to “do whatever you want, whenever you want, with whomever you want,” you need to figure out a way to create a system to serve others.

It is imperative to switch your mindset from that of “consumer” to that of “value producer.”

Getting paid based on your time input mathematically limits time freedom. Since your time is finite, there is a ceiling on your income correlated to how many hours you’ve worked (duh).

While you can certainly make a great living trading time for money, think about how you can still service the end result your unique abilities provide for people WITHOUT your direct involvement.

Figuring ^that^ out is what it means to be an entrepreneur.

Downsides:  “Parkinsons law” essentially states that we are inclined to fill the time we have. If we have more time, we tend to fill it with busyness.

On the flip side, if we are crunched for time, we use that time efficiently. If you have all the time in the world, you’re going to want to work all damn day just so you don’t go broke!

Working late 16 hour days has become a sort of right of passage for bootstrapping entrepeneurs.

With more time freedom…the more obligated we feel to fill the time, which isn’t always a good thing, as this time may cross over into our family and social lives with negative consequences.

It’s important to learn how to put restraints on your working-time in order to be the most proficient. This is the basis to The Four Hour Work Week…maximum output with minimal time input, NOT to actually work 4 hours a week…that’s just lazy.

The other downside to separating your time from your income is that when you’re starting out, the income itself is very sporadic.

The weekly paycheck isn’t such a thing when you first start working off the clock.

I don’t advise anyone to quit their jobs or anything, but if you decide to go it on your own in pursuit of time freedom, make sure you’ve got enough saved up for a few months of living expenses.

You’ll need to fight for your initial self employment income before you can scale your business to the point it becomes as consistent as a normal paycheck.

Definite downside, but again…how badly do you want time freedom?

2. Surrounding yourself with people already doing it

You are the average of the people you surround yourself with. This is no secret, because when you bring people into your existence that truly encapsulate the lifestyle you envision for yourself, the BELIEF that you can truly have freedom of time to do whatever you want becomes a reality.

Belief influences your actions. Actions create the results you desire.

Downsides: My friend Alan wrote about a concept called Lifestyle Isolation.

“No matter how much history, past experience, or mutual love and affection I shared with my communities of friends and family, as I started to work on my first business, there started to become important aspects of my life that my friends had trouble relating to.

And the other side of the coin became true as well: as many of my friends started their post-graduation lives, started families, and made progress down different career paths – there started to become important aspects of their lives that I was less able to relate to.

Different life paths, it seems, tend to present different problems, challenges, limitations, and opportunities, and the more unique mine became (not better, mind you, just different), the more isolated and lonely I felt.”

Hanging out with a new circle whose ideas are drastically different than the norm will cause some strain on your existing relationships. There’s no doubt about it.

I’ve personally experienced a great deal of heartache and lost touch with a lot of my close college and high school friends partially due to lifestyle isolation. It sucks.

First, never forget your roots. Make sure to associate with the people that invest in you, support you for who you are, and believe that you can accomplish whatever you damn well please, and hold them close.

3. Taking control of your schedule

This tip is courtesy of Ari Meisel of This was a massive time hack for me in 2015. If you spend a lot of time on the phone, choose specific time slots on specific days that you want to dedicate to phone meetings.

Then use the online calendar service ScheduleOnce to program in your available time.

Whenever someone needs to speak with you, instead of all the back and forth…just send them your calendar link and say “Here are my available times. Please see if any of these works for you. Thanks!”

They select a time, you approve, and boom it shows up on your calendar!

This limits your talk-time, and you effectively take control of your schedule rather than conforming to someone elses.

Make sure to craft your schedule according to when you do your best work. For instance, I can’t really communicate effectively with other humans until 10am and some coffee…

Downsides: When you take control of your schedule, over time people might come to think that you’re just always busy…Thus, they’ll feel like they are disturbing you if they reach out at any time.

Ultimately, they end up never reaching out at all, since they feel like they won’t be able to get a hold of you, and you get this reputation of never being available…I’ve experienced this from friends and family much to my dismay.

The reality is: of course I want to hear from them! The solution is to have a conversation with the people close to you. Make sure they know that they can reach out to you at all times, because nothing is more important than those relationships. And answer the phone when they call 🙂

And make sure to call your grandparents, because they will always think they are bothering you so just be proactive!

4. Learning to say no

Every time you say “yes” to an opportunity, you’re losing the chance to execute on the next opportunity. Remember, the clock is ticking! To quote the ever wise Derek Sivers from this popular post:

“If I’m not saying “HELL YEAH!” about something, then say no.

Meaning: When deciding whether to commit to something, if I feel anything less than, “Wow! That would be amazing! Absolutely! Hell yeah!” – then my answer is no.

When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”

We’re all busy. We’ve all taken on too much. Saying yes to less is the way out.”

Downsides: You may feel like you’re hurting some people’s feelings when you say no. It is hard to reject an opportunity from someone you otherwise admire, but I believe a “No, because….” is the best way to authentically explain why it isn’t something you can take on.

Just be honest…they won’t be offended.

Also, you may experience FOMO (Fear of missing out) when saying no. If you say no to the next hot investment opportunity, you might miss out on some serious moola. However, the joy of doing something you’re “hell yeah” about gives you more happiness than whatever it is you’ll be missing out on that’s just a “meh.”

5. Use Technology to Automate Repetitive Tasks

For those that know me, you know I’m big on automation technology. In fact, I created a whole software product in the real estate space around it.

To see some of the top tools I leverage in my life to get stuff done (some more than others), check out some of these Cool Tools

Downsides: Using technology to buy back time is becoming dependent on the technology itself. We see folks checking their phones religiously, as we’ve became accustom to the conveniences that they provide. The paradox of automation is that you cannot discount being human.

It is imperative in this day and age to be aware of your dependency, and always try to take the higher ground. We can’t let the robots win! Check out this TED talk from author Sherry Turkle on how to reclaim conversation back into our lives, and not let our phones steal time from human interaction.

There are definite downsides to the pursuit of true time freedom. It’s not for everybody, but the people that want it bad enough will make these sacrifices.

Our life time is a precious thing. Personally, it’s use is not something I want to leave to chance.

Enjoy every moment to the fullest, for “it’s not the years of your life, but the life in your years.”


I'm Dan Schwartz. I enjoy long walks, constant personal growth, and creating things that help myself and others realize the mental state of true freedom. Read more about me at

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