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Why Freedom is the worst goal you can set for yourself 

A shard of ice just shivered it’s way down the spine of very freedom loving, lifestyle designing internet entrepreneur on the planet. Blasphemy has been uttered! Welcome to the sacred cow slaughterhouse.

There’s a solid psychological argument for NOT making “Freedom” your number one objective in life and business. In fact, this most holiest of goals may be causing you needless suffering and self sabotage.

Have you had it wrong all along? Read on to find out what’s broken about the pursuit of Freedom and what you can do to fix it.

Towards vs Away From motivation

The first thing you need to understand about most goals, values or missions – basically anything we’re using as motivation leverage – is that they generally have either a push or pull function.

You know this as the “Carrot vs Stick” principal: You’re either driven toward something you desire or you’re pushed away from a thing you loathe. The two types of drive produce very different results. Someone who is motivated toward financial wealth will produce very different results to someone driven away-from poverty.

Away-From motivation is rarely effective in the long term. It can often be the jolt you need to get moving after a period of inaction, but you’ll quickly run out of steam. A big unexpected bill can surge an unmotivated entrepreneur into action, for example, but once they’re in the clear the motivation will dry up.

This is the source of the oft discussed Feast-Famine Cycle. When you’re trying to run away from something, you slow down once you think you’re safe. Ergo, if your money drive is Away-From you’ll likely cycle between the motivational discomfort of “Not Enough” and the laziness of “Just Enough”.

For the seasoned entrepreneur and reader of this blog, this is all old news. So what about Freedom?

Freedom is not a positive form of motivation 

When most folks think of Freedom, they see jets and tropical beaches. They see sleeping in on Monday and never having to wear a tie.

Freedom means NOT showing up at an office, NOT wearing business casual, NOT having to answer to anyone but yourself.

Did you spot the psychological flaw in this goal yet?

We’re all very clear on what Freedom isn’t. Defining the thing itself though… is tricky.

Look up the definition and you’ll find some variation of the following:

Freedom – The state of not being imprisoned or enslaved 

Turns out every entrepreneur’s favorite value is an Away-From, not a Towards.

Having Freedom means not being constrained in the same way that having Money means not being broke. In fact, you could even argue that while some people are pulled toward Money (Wealth) it’s basically impossible to be pulled toward Freedom in such a positive way.

What is the positive expression of Freedom? It’s impossible to define without listing the things it isn’t. We can only understand Freedom by experiencing the absence of it. It’s unreasonably abstract – you can neither purchase it nor put it in a wheelbarrow. How do you even know when you have it?

The crazy thing is that – in the traditional sense – no one reading this blog has every really experienced a lack of freedom. You might have had to answer to a boss for a while but any corporate employ with $100 in their pocket is literally experiencing freedom when they wake up on Saturday morning.

This may all sound like semantics, but it’s worth sweating the details when we’re discussing the single most prioritized objective for 21st century entrepreneurs. We’ve all been chasing something we already had and… that’s a big problem.

Freedom is binary. You have it or you don’t. You can’t chase MORE of it.

We’re all Freedom lottery winners setting the goal of “getting out of debt”. It doesn’t compute, so no wonder you’re not super fired up on Monday morning.

If my client work over the years has taught me anything, it’s that the happiest and most successful entrepreneurs are dedicated to analogue, fractal and complex outcomes. They make business into art and show up every day to take Leadership, Wealth, Design or something else one step closer to the archetype of Quality.

It can never be perfect or finished but, like trying to draw a perfect circle, you can get so damn close that striving towards one more step of mastery becomes the ultimate practice.

Freedom isn’t like that. There’s no measurement of freedom. It’s debatable whether the guy who owns a jet has MORE freedom when compared to the twenty-two-year-old backpacker who’s lived in hostels for 18 months. I’ve had both as clients and I know which was happier.

Freedom isn’t real

Chasing Freedom is like looking for the end of a rainbow. It’s an optical illusion and there’s nothing really there. You already have it and if you don’t, the only thing really constraining you is your own thinking.

If you want to surf all day, fly around in private jets or travel for a year then make those things your goals. None of them are freedom because – incoming epiphany alert – they all constrain you in some ways while freeing you in others. You have freedom already. You’re not a slave. Goals are goals and jets are objects.

If you define freedom as never having to do anything for anyone and completely playing by your own rules, you’re essentially a hobo. No business owner is totally free in that sense.

If I defined my clients as putting constraints on my time (damn them!) or my staff at Commit Action as unreasonably constraining me with their need for my leadership (screw them all!) then my functional definition of Freedom is going to ruin my life – and a lot of other people’s – if I chose to pursue it.

Seeking to avoid all constraints is infantile. Constraints help you grow. They “inspire creativity” – like Twitter and Haikus. Making yourself write 500 words every morning isn’t very Freedom-y but it will make you happier and your life better. Ditto working out.

Raising capital for your startup is the least freedom-y thing you could ever do, but it gives you a shot at making a difference and joining the billionaires club. Worth it, if you have a great idea and a track record of executing.

Being Free – never having to do anything for anybody – is probably going to result in you not being ABLE to do anything for anybody.

Better to throw it out as an objective altogether. The only caveat is that freedom is something we should be providing – with extreme prejudice – to anyone who is enslaved. For us that already have it (almost everyone), let’s stride towards doing something with it.

Zero consumer debt. The business/management structure and resources to take vacations of your choosing. Being able to cover your personal overhead for a year or so without additional income. Those are good goals to have. I think they’ll give you the feeling you’re looking for. None of them are “Freedom”, but that’s okay.

Beyond that? Aim for the tangible specifics that build a secure, varied, respected, connected and love filled life. If you’re hungry for more, seek to do something huge. Create Quality in your life, in the way you lead or in a thing you build.


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  1. After having read “The 4 Hour Workweek” years ago, I was sold on the idea of “freedom”, although I didn’t quite understand it 😉

    Big mistake. Everything fell apart.
    The irony: Before that, I could more or less work when and where I wanted etc.
    And on what I wanted.

    Biggest. Mindf*ck. Ever.

    Some day I stumbled upon a quote from Seth Godin.
    It made me feel REALLY sick. Not in my head. In my body.

    I wrote it down as a reminder.
    Kind of a short version of your blog post:

    “As an entrepreneur, I’m blessed with 100% autonomy over task, time, technique and team. Here’s the thing: If I maintain that autonomy, I fail. I fail to ship. I fail to excel. I fail to focus. I inevitably end up with either no product or a product the market rejects. The art of the art is picking your limits. That’s the autonomy I most cherish. The freedom to pick my boundaries.”

      1. I hope you didn’t get me wrong.
        Your long posts are awesome!

        They always give much needed context and details.
        They really get into your – äh, my – head.

        I am quite sure that I didn’t internalize all of Seth’s lessons in the way I internalized your blog posts.

        Different kind of masters 😉

    1. Thought provoking post. I like the last sentence of the quote, “freedom to pick my boundaries.” I own a small business that engages me daily in “rolling up my sleeves and getting my hands dirty”. This was not the business I had in mind initially. And yet, it does offer me the freedom of choosing my boundaries and the peace of mind that accompanies that.

      1. Freedom-chaser here 🙂 I’m in the process of “escaping” my current corporate job (ecommerce) to start a solopreneur business. Your post is a much needed kick in the head for me. Here’s how I’m reframing my away-from mentality with more tangible goals:

        1. Away from a private label retailer business model toward one where I can design my own products (software-enabled personalized prints) and constantly improve quality.
        2. Away from an end-to-end supply chain (sourcing, importing, fulfilment, reverse logistics, cash reconciliation) that entails overhead and headaches toward a personalized print-on-demand process where I can focus on product design, marketing and customer service.
        3. Away from an input-based career with fixed working hours inside an office to an output-based one where I’m compensated based on the value I create and penalized for my laziness.

        Right now I’d like to push myself to see how much I can accomplish alone. I imagine that I’d reach a point when a desire for further growth or plain loneliness will allow me to take on the responsibility of leading a team without seeing them as a constraint on my freedom.

        Thanks Peter!

  2. Peter this piece is amazing! You managed to sum up all my thoughts into a digestible little nugget that i want to take with me everywhere and read like a love note when my mind gets “mind-f*cked” (as Stephen says) and my millennial butt gets overly lazy.

  3. I have been involved with my. Own business and found it impossible to stop working on my projects. What can I do to separate this business from my free time?

    Best regards,

  4. Hey Peter!

    Great article and really got me thinking. I behave exactly as you mentioned. Apparently when I got a little bit of freedom I get lazy until I feel trapped again.

    I am familiar with your work and therefore I ask: How could I best reverse the issue. Is it just done by setting goals like you mentioned?

    1. Yep! Just ditch the notion of freedom altogether and focus on tangible outcomes that will make you happy. Chasing Freedom is just chasing a state of mind … and you can have it right NOW anyway.

    2. Hey Sebastian,

      maybe the concept of “systems/processes over goals” may reverse this issue?

      What I mean is instead of having a goal of making $xxxxx / month you want to have the “goal” of having the system/process of writing at least x amount of words per day, working out at least x hours a day, call at least x persons a day and offer them your help or find at least x amount of customers a month.

      In other words: you have a fixed routine that you work through each day. And the goal merely is the indicator if you do your processes correctly/succesfully.

      Or: your goal is to have a process that you follow religously.

      Let me know if this has helped you.

      Sending Love,

  5. Love this. Freedom is really important to me – in all sorts of ways (not so much the margaritas on the beach scenario but I have my own definition). And you’re right – it’s too amorphous to strive for. What does it really mean? So I also aim for tangible. And I use my ‘freedom’ yardstick to help me make decisions. Help me set my boundaries for what I do and don’t want to take on. So I can work with a sense that I am living my freedom. And still aim for the specifics.

    1. Hey Cathy! Sounds like you’ve put together a solid workable definition for what you’re aiming for – precisely the point of this article! Thanks for stopping by to comment 🙂

  6. Hah, Peter!

    This is smart, actionable and timely. And your commentators are really rocking it today, as well. The company you attract says a lot about the “quality” of what you send out.

  7. Once again a genius Peter! Could you be more in tune with us? I think not. I ride the feast and famine roller coaster and now I know why. …. Geez so simple, I feel silly. Ok. …I promise to apply! Sometimes a great kick in the ass to undo the ……4 hour work week. ….mind fu%! K….. as an example, is just what I need. … Thanks Peter!

  8. Fantastic post and it explains my up and down motivation style of the past few years. I will now shift my focus towards something more tangible: improving the quality of the services I provide and a solid focus on my financial goals.

    Verrry helpful! Thank you!

  9. “Don’t look to become a person of success, look instead to become a person of value.” Albert Einstein

    Everyone knows when they don’t have freedom but few of us know how to be happy with our work and our life. I think the quote by Albert Einstein has the answer but it requires you to commit to a path of delivering high value to other people and this isn’t easy to do.

    I think one of the biggest motivations is a search for meaning and if and when you find your personal meaning and you are willing to work towards it everyday then you will experience Freedom on its highest level. It’s hard see your life from 30,000 feet when you are working everyday in the trenches.

    Peter always helps me to rise up to 30,000 feet and question everything I hold sacred here on the ground. Thanks for this post and it couldn’t have come at a better time for me.

  10. BRILLIANT! Thank you for this, Peter. So perfect, helpful and timely as I’m pivoting in my business right now. Away from “freedom” and towards connection, collaboration and meaning. After a year of lonely, long-hour, pajama-clad, frustrating days, I’m running towards set work hours, high heels (yes, please!), collective mission, teamwork and waking up on Saturday mornings with $100 and two days to spend in play with the people I love.

    Here’s to more articles and wisdom like yours!

  11. Bravo! I shall reread your post as medicine. Mahalo.
    “To live content with small means; to seek elegance rather than luxury, and refinement rather than fashion….In a word, to let the spiritual, unbidden and unconscious, grow up through the common. This is to be my symphony.” ~William Henry Channing

  12. You just can’t control the clock. You can only manage it and balance your goals. Just pick the ones that you can live off of and hopefully enjoy doing that also allows you to do the personal things you want to. Winning the lottery won’t hurt either; you can find the right numbers next to the pot of gold at the end of the rainbow.

    Get a job or company that you like that provides for you and your family that doesn’t consume all of your time. That’s the trick. I had that for a couple of years but everything changes, darn.

    Good Luck

  13. Hey Peter,
    your homepage just made me smile 🙂

    “Wealth | Freedom | Sanity
    … Hit all three, and what happens next is amazing.”

    and below:
    “Why Freedom is the worst goal you can set for yourself”

    Of course I understand what you mean by that.
    But in a way… you might be fueling the unhealthy freedom chasing with this title?

    1. hehehe I was wondering when someone would spot that. Actually, this is common – long time readers of this blog will know that my favorite thing to do is contradict myself. As Walt Whitman once said “… I am vast. I contain multitudes” 😉

      The truth is that while I think – psychologically – freedom is a value we should not focus on too much… the reality is that my homepage exists to hook entrepreneurs IN and make them part of my tribe. And those folks just discovering me for the first time are DEFINITELY interested in Freedom. They just don’t know what’s good for em… yet.

  14. Great article Peter.

    In my head freedom isn’t a standalone word so the need to define it doesn’t really arise. It’s a channel towards positive things. So I don’t want [standalone] freedom. Like you I agree that it’s difficult to define. I want the freedom to [positive thing goes here], e.g., to spend more time reading, to have the flexibility to take time off to attend my children’s performances, etc. So for me it’s not an end in-itself and is also a carrot rather than a stick.

    Take care,


  15. Great post and wise words that more seasoned entrepreneurs will nod in agreement with – freedom per se is an illusion.

    That other guy with the initials DS refers to it as freedom of finances, freedom of time and freedom of relationships.. which is how you have described the fruits of a well orchestrated company. And when mentioning time it’s not that it’s all your own, it’s just that you get some choice on how it is spent.

    Also, great point about always needing some resistance to push up against, otherwise there’s no improvement.. you can’t build mental muscle without resistance.

    Agreed, measured doses of freedom in certain areas is probably the ideal end-goal.

    ..this doesn’t mean you can’t have shiny things and an enjoyable varied life as well 😉

    1. Hi Michael! I think variety alone is almost a better value when it comes to increasing happiness. We love for things to be different! Pursuing variety in a bunch of areas (where you live, the type of work you do etc) is a great proxy for the Freedom feeling people want.

  16. “Aim for the tangible specifics that build a secure, varied, respected, connected and love filled life.”

    Which are?

  17. It just jumped out and hit me. A staggering revelation. I sat with head in hands, gazing in wonderment at the words on the screen. All I can say is thank you.

    Your post reveals something I’ve never grasped or understood until now – a simple explanation of why feast-to-famine has dogged my entire working life. Why self-sabotage and procrastination constantly threaten to take me over completely and the underlying reason I’ve failed to perform to my own expectation.

    “If your money drive is Away-From, you’ll likely cycle between the motivational discomfort of “Not Enough” and the laziness of “Just Enough”.

    Having truly experienced a blinding flash of the obvious, I’m rushing around in a spin. What is the fastest way of converting my new self-knowledge into action?

    1. Hi Steve! Glad this one hit home 🙂

      Moving from an away-from motivation habit to a “toward” mentality is a tricky thing. It requires you to really think through your goals and make sure you have short, medium and long term positive outcomes that you’re focusing on.

      Honestly, the best resources I’ve created on the subject are over at – you should check that out if you’re serious about making changes.

  18. This is a very insightful piece! I’ve been an entrepreneur for 28 years.
    My Dad moved to the the US in the 50’s to open a blacksmith shop at the racetrack. Everything I learned about business I learned there. He struggled to make ends meet, but made that shop into a huge success.Iit wouldn’t be the big things, it was all the small details. Paying attention to each horse and trainer, and remembering how special each client was, offering small things like a daily paper, coffee, it ended up being the “it” shop where everyone wanted to be!
    Years later I would open my own studio, and I made a grocery list of everything I hated in studios and swore mine would be is, and also very successful. It’s all the little things, it’s the thought and time and effort put into every workout.
    Since we handle people in the music business I always say if you have “nothing to say, you have no song to sing!”
    For an entrepreneur the business IS your song to sing, it can’t just be for the money, power, or prestige, it is the thing that you do better want to do better than anyone else!
    Love your work!!

  19. I am so incredibly glad I found this blog. After reading it, I realized why I’ve been so unhappy lately. Instead of focusing on what I love to do, which is solve problems, I’ve been obsessed with creating the “freedom” life style, which honestly would just make me miserable. Sitting on the beach all day would give me sunburn. Solving project issues and delivering exceptional products to clients, that’s what I enjoy.

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