Do the Uncomfortable Work


If you’re unhappy with your current situation in life, whether you’re working an unbearable 9-5, paying off a mountain of debt, or simply feel stuck, I have good news:

There is a way out. There is a tried-and-true method to overcome any obstacle, any hindrance, any hurdle you currently face:

Do the uncomfortable work.

Uncomfortable work is exactly what it sounds like: work that we know we should do, but often avoid doing because it makes us temporarily uncomfortable. It’s the work that crosses our brain when we wake up, the work that we keep putting off, the work that we dread doing.

There are times when we blatantly ignore doing this type of work. We know we should update our resume, but we opt to watch Netflix instead. We know we should work on that blog post, but instead we scroll aimlessly through social media.

But there are also times when we avoid doing uncomfortable work by instead doing what feels and looks like work. It’s when we change the layout and font size of our resume instead of actually adding to it. It’s when we change the theme of our website instead of writing a new blog post. Or when we post on Facebook about a new project we’re starting instead of actually starting it. It’s when we tell our friends we’re looking into setting up an IRA instead of actually setting one up.

This type of behavior is particularly dangerous because it tricks us into thinking we’re doing real work when in reality we’re doing everything except the work. 

But there is no hiding whether or not you have been doing the uncomfortable work. The position you’re in right now is a reflection of how much time you have spent doing it.

Willingness to do uncomfortable work is what separates those who have control over their life from those who don’t. 

Every single person who has ever retired early in their 30’s has done a huge amount of uncomfortable work. There are no exceptions. There simply isn’t a way to achieve financial independence without doing grueling, difficult work at some point. 

Anyone who has paid off a significant amount of student loan debt will tell you firsthand how uncomfortable they had to be at some point, how many short-term sacrifices they had to make to become debt-free. These people picked up a second part-time job, they worked long hours, they sacrificed dining out, they lived below their means. They endured uncomfortable work to get out of debt.

Any student who has graduated with a valuable degree will tell you how many long hours they had to spend in the library, how many times they wanted to quit but didn’t, how many times they had to choose studying over Happy Hour.

Any person who actually gets to dictate how they spend their time each day has only reached that position through doing uncomfortable work, and often for many years. People that achieve this freedom have had an important realization:

The exact work you dread doing most is the work that has the most ability to change your life.

If you hate your job, there are so many different paths you can take to land a better job. You can start taking online classes, or send off your resume to new companies, or even start your own internet side hustle to build up a freedom fund. But these are the exact actions we often procrastinate doing. I’ll get to it eventually, I’ll do it when I have more free time, I’ll do it next weekend, I’m too tired to do it now. 

The more you delay doing the uncomfortable work, the longer you remain stuck in your current situation.

The truth is, most of us know exactly what we should be doing to improve our lives, but we simply don’t feel like being uncomfortable in the short-term even if it means freedom in the long-term. Most of us don’t lack knowledge, we lack discipline. We would rather lay on the couch watching Seinfeld than work on our side business. We would rather go out drinking with the bros than sit down at the kitchen table and set up a budget. 

What are you doing outside of your day job? Are you spending time reading, building a side business, learning new skills, hustling at a second part-time job to pay off your debt? Are you researching ways to save more money, earn more money, and gain new knowledge?

Or are you taking the approach that 90% of people take – spending every waking hour outside of your day job staring at social media feeds, watching TV, and spending time at bars with people you don’t even care about? The majority of people who take this approach never gain control over their time. They never acquire freedom because they aren’t willing to do uncomfortable work.

In every situation we always have a choice: Do we want to remain in this position or do we want to do the uncomfortable work to get to a new place in life? There is always something we can do to gain more freedom, but the question is: are we willing to do it? Are we willing to experience short-term discomfort for long-term joy?

Most people aren’t.

It’s easier to remain in the same situation,  the same routine, the same dull daily habits we’re accustomed to instead of getting uncomfortable and clawing our way out of a bad situation to reach a better one. I realize this isn’t the advice most people want to hear. They’d rather hear about some get-rich-quick scheme that will turn them into a millionaire in six months. But this isn’t realistic.

There is only one proven method to cultivating a life you want to live:

Do the uncomfortable work most people aren’t willing to do in order to gain the freedom most people will never experience.


Zach is the author behind Four Pillar Freedom, a blog that teaches you how to build wealth and gain freedom in life.

Zach's favorite free financial tool he's been using since 2015 to manage his net worth is Personal Capital. Each month he uses their free Investment Checkup tool and Retirement Planner to track his investments and ensure that he's on the fast track to financial freedom.

His favorite investment platform is M1 Finance, a site that allows him to build a custom portfolio of stocks for free, has no trading or maintenance fees, and even allows him to set up automated target-allocated investments.

His favorite way to save money each month on his recurring bills is by using Trim, a free financial app that negotiates lower cable, internet, and phone bills with any provider on your behalf.

His favorite micro-investing app is Acorns, a free financial app that takes just 5 minutes to set up and allows you to invest your spare change in a diversified portfolio.

His favorite place to find new personal finance articles to read is Collecting Wisdom, a site that collects the best personal finance articles floating around the web on a daily basis.


Full Disclosure: Nothing on this site should ever be considered to be advice, research or an invitation to buy or sell any securities, please see my Terms & Conditions page for a full disclaimer.

6 Replies to “Do the Uncomfortable Work”

  1. I know what you are saying but honestly I succeeded wildly without ever feeling like I had to work hard at anything. Engineering was easy in college and work was like play once I graduated. Pretty soon I was running the company. I think it is a mistake to assume everyone had to work hard to succeed. If you find the right niche you never have to work at all!

    1. Steve, that’s great to hear! It seems like you found the perfect niche for yourself. I would argue that most people don’t find success quite as quickly as you though. Even if the road is smooth, there are often bumps along the way and doing uncomfortable work is what helps overcome these bumps along the way. Thanks for the feedback!

  2. “This type of behavior is particularly dangerous ”

    Also with this, people delay and delay and delay because they think they’ve actually accomplished the work. One suggestion to make the uncomfortable work at least easier is to break it up into parts. For example, I had to repaint my kitchen and baseboards recently. So I painted in 3 nights by sectioning off the whole project into thirds. It made it a lot easier than doing it all at once and I didn’t mentally rush myself because I planned it in such a way. When breaking work off into smaller parts I find I do a better job (even with posting blogs, but I guess the readers would decide that :-).

    1. SMM, I also find that breaking down tasks into smaller pieces and tackling one piece at a time is one of the best ways to get work done. And, like you said, this often allows us to do a better job because we’re not rushing to finish it all at once. Great insight 🙂

  3. I give my kids the same advice (far too often if you ask them): don’t take the path of least resistance. Or, put a bit more bluntly, don’t be lazy.

    We often know exactly what we should do, but there’s almost *always* an easy way out. Taking the easy way out doesn’t usually lead to extraordinary results or personal growth. Do what you know you should do. Don’t take the path of least resistance. Do the uncomfortable work. Enjoy an amazing life!

    1. Your kids will thank you some day for instilling those values in them! I agree with you, there’s always a little voice in the back of our head saying “Just do this later”, “Just put it off a little longer”, “It’s too hard”, and it’s our job to constantly fight this resistance and do the uncomfortable work anyway because it’s what will allow us to live an incredible life. Thanks for the feedback, Ty! 🙂

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