Why Everyone is Holding You Back

By Sean Ogle •  Updated: 01/29/22 •  6 min read

This post was originally published on Location Rebel in October 2010, right after I returned from a year of living in Thailand after quitting my job. I’ve kept it published because I think it’s important to see the mindset of someone less than a year into quitting their job and starting their own business. You’ll have ups and downs. Learn what is holding you back, and focus on yourself.

For the longest time I had goals in the back of my mind that I’d been hoping to take action on, but wasn’t.  Things like traveling to Brazil to dance in the carnival parade, starting a business, and living abroad; these were all vague concepts that I’d wanted to explore, but my traditional American mindset kept me from actually doing anything about it.

Or did it?

It took me awhile to realize it, but it wasn’t just my mindset that was holding me back.

It was actually the people that surrounded me who were keeping me from pursuing the things that actually got me excited in life.  You see, (unhappy) people who follow a traditional way of thinking have made it their goal, consciously or not, to make sure you follow the same path they were on.

For many people, this could be in the form of a boss who’s been unhappy in their job for far too long – and they want to see others follow in their footsteps to validate the decisions they made.

It could be parents who are 22 years into their 30 year mortgage that worked for the same company for their entire career – and feel that you should do the same.

Or maybe it’s even your best friends that are pulling down 100k a year and cruising around in their new BMW’s – it can be pretty tough to tell them you’re quitting your job to head to the islands in SE Asia for an indefinite period of time.

(Don’t think I don’t see the irony that I’m now making six-figures and am onto my third BMW).

No, for most, their personal mindset is just a small portion of what keeps them from being unconventional – it’s the mindset of everyone around them that really hinders action.

What is Holding You Back?

I’ll provide an example from my past.

When I was at my previous job, there was a period of time where the stock market was crashing and revenues in our company (along with every other financial company in America) were taking a hit as well. My boss mentioned on a couple occasions that if I had any creative ideas for saving the company money, he’d be open to them.

This was right around the time I began Location Rebel. I wrote a post called “Sail the World – for Free”, which you may surprised to find, wasn’t actually totally theoretical.  I met a guy who needed an extra crew member to help him sail his 47 foot sailboat through the Caribbean.  All expenses paid, aside from the $250 plane ticket down to St. Maarten to meet him.

Dream come true right?  I was going to start my newly founded bucket list off with a bang and immediately cross off #13: Learn to Sail. I proposed a 2-month sabbatical that could have saved the company upwards of $10k, and I’d get to have a pretty life-changing experience.

Now I’d like to think the reason that he didn’t go for it really was that I was indispensable, but given the nature of the company, I don’t think that was the case.

Rather I think it came down to the fact that they weren’t afforded the ability to take such a trip themselves, and certainly didn’t feel as though I should have the ability to do so.  Hell, I was just a 24-year-old kid.

I shouldn’t be able to do stuff like that until I reached retirement.

I’ll make another much longer story shorter, but when I submitted my remote work agreement a few months later, I believe the reason it wasn’t accepted wasn’t due to anything business-related (after all they would have saved tons of money, and I would have been able to do nearly everything I did in the office remotely), but for the same reason that I didn’t get to sail.

I would have had a baller lifestyle, while they were unable to.

Side note: Yes, 25 year old me who originally wrote this really did say “baller.” It wouldn’t be the last time, either. Cringe…

I suppose that’s the price you pay for being young, ambitious, and full of creative ideas.

I’d like you to think about this for a moment as it pertains to your current lifestyle and your goals for the future.  What do you want to be doing that you aren’t currently making progress towards?  Is it because of financial reasons?  Fear? Other priorities?  Or have other people in your life determined your current path without you realizing it?

The vast majority of people around you will discourage you from living an incredible lifestyle, simply because they don’t have the courage to do it themselves.

Or in some cases, they didn’t have that courage when they were younger and now are stuck with an overwhelming amount of responsibility that stands in the way of that change.

I’d like to make it clear that I know there are a ton of people with careers they love and “conventional” lives that are perfect for them.  Don’t think I’m talking crap about you, if you truly are content with that, then that’s awesome and I’m stoked to hear you found that happiness.

No, I’m writing this for the people who aren’t being honest with themselves.  The ones that are living a mediocre life because it’s the easy thing to do.

I have a course inside Location Rebel Academy called Overcoming Uncertainty. In it, one of the things I ask people to do is write down everything that’s keeping them from taking action towards their goals.  For most, the honest answer is going to be related to someone else.

You’re working on your boss’s terms and can’t break out of that…

You think your parents would be disappointed…

Maybe your spouse or friends don’t get what you want to do…

I encourage you to take an honest assessment of your situation and think about the people who may be holding you back.

Then ask yourself if you’re happy with being held back.  If so, awesome, nothing left for you to do.

If not, it’s time to start doing some work and figuring out how to start kicking some ass.

So who is holding you back?  Is there anyone in particular that is dictating how you live and the decisions you make? Recognizing that is one of the best steps you can make to mentally prepare for any change you hope to make in the future.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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30 comments on "Why Everyone is Holding You Back"

  1. Alex says:

    Great post Sean. Really puts things in perspective. It’s my life, and I need to put some emphasis on what makes me happy rather than catering to others. Nice solid point made.

  2. Joel Runyon says:

    I’m gonna combine two of your above statments into 1 that I think describes a huge mindset we see –
    “I shouldn’t be able to do stuff like that, while they’re unable to.”

    That’s so true. Often people hold us back because they can’t see the possibilities you can. It’s like the caged monkey story Chris tells in his book. Good stuff Sean 🙂

    1. Sean says:

      @Alex Glad to see you got some value out of it, I’ve spent enough time catering others, sometimes you just need a reminder to realize that its actually happening!

      @Joel I think that is one of the fundamental components of life and human thought. So many people have the mindset that “if I can’t do it, you can’t either”. I say false, erroneous on all counts!

  3. Michelle says:

    This is so right on! I think most bosses and companies in the world are like this, and it makes sense from the standpoint of an assembly line, where all the cogs have to fit together the same way, and making allowances for differences can cause the machinery to slow down or halt. Now days the companies that run things like a machine are having a hard time getting people to do their jobs properly because no one feels valued, therefore they no longer value the company. The companies that are thriving are doing so because they have chucked the machinist culture and are doing things on a more human level, which allows for creativity to grow. Sounds like when your boss asked for “creative” money saving ideas, what he meant was a “business as usual” idea that happened to save a small amount of money. Sad to think this is what I will be up against my whole career, unless I end up launching my own tiny business someday.

    1. Sean says:

      @Michelle, thats a really important point you just made: “no one feels valued, therefore they no longer value the company”. So often employers forget that their #1 key to success is employees that feel valued and believe in the company. As soon as they lose that, the company is in big trouble.

      Also, no reason why you can’t launch a tiny business now! Just because you have a career doesn’t mean you can’t spend a couple hours a week building something for yourself 🙂

      @Richard That’s a really important component, that I’ve run into as well. For the past year I’ve been incredibly selfish, basically choosing to follow my own path rather than being a good friend, boyfriend or son (ok, I havent been that bad, but I’m trying to make a point haha). However, my point is that taking the last year to focus on myself, has allowed me the time now to spend more time with friends and family. While I still have a ways to go its the hard work and success I’ve seen building a business that will give me more free time over the long term to spend with the people I enjoy most.

  4. I would say that, for me, its not people holding me back because they are too afraid to live the lifestyle that is holding me back, but it is me doing it to myself because I feel obligated to help them/spend time with them/etc.

    For instance, a local band asked me to play bass with them because their bassist had just quit and they were in dire need of someone stat! I felt obligated (because they were my friends) to help them – which has subtracted 4 hrs a week from my free time (not including shows).

    Another example is my parents. Since I’ve moved out (which I did in part because I wanted to be left alone to work on my business projects) I’ve felt obligated to spend time with them which includes going to movies, eating out at restaurants, etc.

    The fact is, all these little things that I’ve been doing for other people due to a perceived notion of obligation truly add up to a lot of time NOT spent on creating the life that I want.

    Trying to live a balance life is quite difficult the more you create responsibilities and obligations for yourself.

  5. You’re absolutely right that a lot of people need self-validation and therefore they don’t want to believe you’re capable of living remarkably (and a rare few consciously want to see you fail), but I hope readers don’t place too much “blame” on others. Ultimately it’s oneself who lets other people dictate what they do and where they go in their lives. It’s a hard choice in some cases (if it’s friends or family) but the responsibility lies with you to take life by the horns.

  6. Ryan says:

    I think a major way people are held back is through others’ nonverbal communication. The body language, facial expressions, tones of voice, as well as what the attitude of what is and is not expected really creates the most dead weight on an individual seeking to be different… You’ve done a great job breaking out of the mold!

  7. David says:

    Hey Sean!

    Great Post. Recently I got a message from a former Professor that was along the lines of “It’s nice that you are living this fun live. Just be sure to do do something responsible once you approach 30.”


  8. ChaChanna says:

    Stellar post! Okay, this is my favorite line. “The vast majority of people around you will discourage you from living an incredible lifestyle, simply because they don’t have the courage to do it themselves.” You hit it right on the head there. I do also believe that people limit others based on their limitations. It’s unfair, especially when it’s parents that do it to their children. Just because you are stuck at a job for all your life doesn’t mean the rest of the world has to.

    I also think this way of thinking is why the next generation is having a hard time at work with the senior staff (otherwise known as old people. They realize that life is more than a job and want to actually enjoy their lives while older workers are thinking that is not how they work so why should these young whipper snappers get to have a work/life balance.

  9. colin8ch says:

    Very cool post Sean! Great story and scary how familiar it is to my story. I was surrounded by people who were saying “but you’ve worked so hard to earn your way up to Vice President, to a new BMW, a motorbike, you have 4 weeks of vacation a year and you’ve built a dream home, blah, blah… and now you want to walk away and start your own business??… your crazy.” The material stuff I received as a reward for working in the corporate world doesn’t mean shit to me, the most rewarding, fulfilling thing has been building a business that is helping other people succeed with their online business and enjoy their life of freedom and mobility.

  10. Not many people are bold enough to break the trends and go for their dreams these days. Seeing others do this does bring feelings of envy and jealousy. But hopefully, in the long run, people like you can help inspire these people to see that living their dreams is possible!

  11. Julia says:

    You know how else people around you can hold you back? Those who move up in their careers, get bigger titles, recognition, seniority and money seem more…successful in professional way–while you, who are deciding to quit your job and say, travel, will have to keep starting somewhere else as a beginner. And do that again and again.

    And you have to come to terms with that concept of starting over, and be ok with it. While it’s easy in theory, many of us aren’t all that comfortable with that in practice–especially in light of our more “successful” friends who are “moving up in the world”.

    It’s the minority “nomad” mentality vs. majority “career track”. Becomes hard to convince others sometimes that my willingness to do many interesting projects instead of having one employer, travel around, and move to a different city on a whim is part of the adventure rather than a frivolous waste of time.

    Thanks for the post!

  12. Emily Youngs says:

    Very timely post for me, Sean! Still working up the nerve to create a life on my own terms… thanks for the extra inspiration!!

  13. Will says:

    A lurker here coming out to say… Thanks as usual for the great words Sean.

    It seems that most people around me are happy with their life, many of them fall in that category you talk about, happy making their 6 figures and just being ok clocking in and clocking out every day, driving the BMW, a slave to the car payments and mortgage.

    Every idea, every book mentioned and any inkling not to conform to this standard is hit with descent and a nose in the air plus “That’s crap, it won’t work!”

    Sure it would be awesome to point the finger and blame them, but I ALLOWED their words, criticism and idea of living hold me back.

    I’ve been holding me back and like you said … “…it’s time to start doing some work and figuring out how to start kicking some ass.”

  14. Great post, Sean. This statement, in particular, really resonates with me. “The vast majority of people around you will discourage you from living an incredible lifestyle, simply because they don’t have the courage to do it themselves.” When I really think about it, this makes a lot of sense. In order to truly be happy and live the life that you want to live, it’s going to most likely require you to make tough choices and perhaps alienate a few people. It’s a tough call. But when you set out to achieve your goals and aspirations, you discover quickly who your true friends and supporters are. Those that get jealous or try to talk you out of your dreams are probably not the friends you want to surround yourself with 24/7. Thanks for writing this post and really breaking down the keys to creating a life on your own terms.

  15. Hi Sean,

    Dang this part truly hit me, “No, I’m writing this for the people who aren’t being honest with themselves. The ones that are living a mediocre life because its the easy thing to do.”

    I think I have been sticking to what is easy to do, to what which is “comfortable” when the truth is at the back of my mind I would dream of doing something else and complain about what I have been doing with my life. I have been working with the same company for more than 3 years and I feel stuck, not growing and totally put myself into a shell that I don’t think I could easily break in. Maybe due to some reasons that you mentioned such as fear, fuzzy goals and yes, I easily get influenced by people around me (whether subconsciously or not). I have always wanted to quit but have been waiting for something to change. Only to realize I need not wait for change, I need to MAKE it!

    And the first step towards getting to where I really want is to leave where I’m currently at.

  16. Matt says:

    One of the things I am going to enjoy about this next year is proving to people that you can do amazing things regardless of how old you are and regardless of whether you have a family to support. I’ve had people say it’s that at my age it’s reckless to uproot my family and move overseas. They always bring up how I need to be making a lot of money; don’t give up a secure job; think about your retirement. I say it’s reckless to live a life that doesn’t make you happy, that doesn’t leave you feeling fulfilled and that doesn’t give something back to the world. Sure there will always be people in our lives that whether they mean to or not will say or do things that make us pause. But really the final decision on whether we will make that leap or cower back from the ledge rests with us. I’m choosing to take that leap. As always thanks for your encouragement and support Sean.

  17. Julia says:

    Another wonderful post, Sean!

    I haven’t felt that others were jealous of me. I felt that they didn’t trust me, didn’t believe in me, and eventually, that they just don’t get me. Those closest to me used to talk me out of my crazy ideas. They’d let me talk about my dreams, but when I started thinking seriously about taking steps, they’d talk me out of it.

    Then I started doing stuff without consulting anybody. Once they started hearing my stories after-the-fact they switched to a I-don’t-think-you-should-but-you’re-gonna-do-it-anyway type of attitude.

    I think they’ve finally accepted that I want something different from what they want. Now I share my ideas and they say “If that’s what you want, good luck” I guess I must be lucky 🙂

  18. Bill says:

    Great post.

    I am the parent you describe – years in to my mortgage, more years with the same company I started with – with no plans to leave any time soon.

    I have seen young people leave their jobs at my company to go explore the world. Unlike many around me, I say, “What a great opportunity – leave now and never look back”.

    I know that these exceptional young people would forever regret not going to Paris, India, Ecuador (wherever) instead of sitting in a gray office waiting for death.

    I only wish I had had the courage to explore when I had the chance. I will not make the same mistake with my own kids. I have a few years to finish my commitment to them and then I am right behind them on the nomad trail.

  19. Quinn says:

    What I get a lot of time is when my friend ask me what I’m up to they say : “Tell me everything, I live vicariously through you.” I cringe. That’s great that they are interested in my life, but I have no desire to be told that my a dear friend. Don’t live vicariously through ME, live FULLY through YOU!!

  20. Guy says:

    Excellent. As someone looking at 50 coming up fast this is so true. I also saw a young man quit our office to back pack across Europe for 2 months. While others (who were stuck) told him he was messing up, i told him that if he didn’t do it, he would be “looking at 50 coming up fast” and pissed at himself that he didn’t do it while he had the chance.

  21. Sean, what are you up to now? Where are you?

  22. Kevin says:

    While I agree that jealousy is likely a factor here, I think you need to look a little broader, too. The fact is, if they allowed you to work from home, then they’d have everyone else in the office asking for the same treatment. “If Sean’s allowed to work from home, then I should be too.” Maybe management was concerned that not everyone has your work ethic, and productivity would suffer.

    I can appreciate their stance, it’s difficult to please everybody.

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