When “Comfort Zone” Is SO Uncomfortable
- Timothy Iseler

- Mar 2
- 7 min read
Do you watch the show “Queer Eye”? The Fab Five always meet with someone who needs help getting out of a rut, sometimes in simple feel-good ways and sometimes in really emotional, tear-jerker ways. But the person getting the make-over is never doing super great on their own. That’s the whole point of the show.
In the most recent season, the Fab Five meet with a single mom who is super resistant to any kind of help. She doesn’t want to do any of the activities, doesn’t want to have any of the conversations, and is generally kind of combative about the whole thing. It makes you wonder why she agreed to be on the show. She keeps telling them, “no, I’m happy the way things are,” “no, I don’t want to change,” but she is clearly struggling.
Eventually she agrees to participate in some activity, dipping a metaphorical toe in the water, and she starts to open up and the episode ends on a positive note. But holy moley she did not want to get out of her comfort zone.
And that’s what I want to talk about today.
So I run my own financial advisory business and, to be perfectly frank, no one reaches out to a financial advisor because they’re super confident about how things are going. People have problems, questions, or concerns, and they’d like to resolve them with the help of a professional.
Broadly speaking, the people I work with tend to fall into two categories. There are the people who have a timely problem like receiving an inheritance, approaching a milestone like retirement, or maybe they just filed their taxes and want to know what they can do to get ahead of next year’s tax bill. Those types of issues have a time sensitivity that make you want to take action right away.
Then there’s the other kind of problems: the ones that linger for months or even years before a person is motivated to act. Examples of these types of problems, questions, or concerns usually start with “I should”: “I should make sure I’m saving enough for retirement”; “I should update my estate plan”; “I should figure out if I’m investing the right way”.
The reason these types of “I should” problems are so hard for people to address is that there’s always a reason — dare I say excuse — for why now isn’t the right time, but some other, hypothetical time later will be much better.
And that is how people end up in the so-called comfort zone.
The phrase "getting out of your comfort zone" is used so often that it's a cliché—but we all kind of know it's correct, right? If you only stick to the familiar, what feels safe, the normal way that you've always done it, there's really no room to grow or improve. Getting into a groove is awesome; but if you stay in a groove too long, it becomes a rut. You need to push the boundaries of what’s familiar in order to move forward in life.
But here’s the funny thing: very often, your "comfort zone" actually feels really ... uncomfortable. In fact, we only use that term when something isn’t working. In other words, a person who needs to get out of their comfort zone is usually already uncomfortable. Isn’t that weird?
Typically, people wait to take action until the discomfort of that comfort zone exceeds the fear of the unknown. The irony, of course, is that it would be much easier to make changes at any point along the way than to wait for all of that pain or discomfort or frustration to get so big that you can’t take it anymore. That can mean extra years of unhappiness, all just to avoid upsetting the status quo. Seems like a high price to pay, right?
So what happens when you notice that your so-called comfort zone has become … downright uncomfortable?
Today I want to share five ideas for how you can break out of your comfort zone, all of them chosen to make it as easy as possible for you to take action and stop procrastinating.
Ok, let’s talk about starting small. When you feel like you don’t have the bandwidth to do something you know you should do, I think a great place to start is with the easiest possible positive action. You don’t need a grand gesture, you don’t need to hit a home run, just get started with the absolute easiest thing to do. Then do it again tomorrow. Then again the day after that. It takes an average of about 66 days – just over two months – to build a habit, so it might feel like work at first. That’s why we want to start small. But the cool thing about habits is that, once established, they have their own positive inertia. It starts to feel normal to do the thing that initially seemed like a big step. When you get to that point, it's your cue to start the next easiest thing to do. Pretty soon you’ll be doing things that seemed totally impossible before you got started.
Number two: don’t let perfect be the enemy of good. If you’re waiting for the perfect plan or the perfect time to get started, I have some bad news: perfection is not real. It’s both a barrier you will never climb and it’s a moving target. So throw perfect out the window; it’s not helpful. But a good plan that you can actually stick to? That opens up all sorts of ways to move forward. Here are some ideas when it comes to your money: spend a little less than you want; save a little more than you have been; repay debt a little faster than you have to; and invest in things you can own the rest of your life. Those are all good ideas that you can stick with, which beats perfection any day of the week.
Next, choose actions that are easy to change or repair. Getting out of your comfort zone means trying new things, and sometimes that can feel risky. Like, what if I try this and fall on my face and everyone sees it? No one wants that. But you can minimize that risk by choosing actions that are easy to change or repair if they aren’t working. Here’s an example from investing: if you put all of your money in one investment and that investment tanks, you’re sunk. This is a decision that is not easy to change or repair. How about this instead: you take your money and invest in a mix of funds that track U.S. and global stocks and bonds, so that your money is now spread across hundreds or even thousands of companies. If any one of them doesn’t do well, that’s ok; your eggs aren’t all in one basket. If you decide over time that you want to swap one fund for another, you can do that without radically changing your overall investment strategy. In other words, you can easily change or repair anything that isn’t working for you.
Number four: Make a plan & write it down. Listen, I’m no psychologist, but there is lots of evidence that suggests that writing down your plans impacts your likelihood of sticking with a plan. And I mean physically writing, with a pencil & paper; it’s not enough to just think of a plan and keep it in your head. I heard a phrase once that describes this situation: building castles in your mind. Isn’t that a great phrase? If your plan stays in your head, you can tweak and improve and change it endlessly. This is another form of chasing perfection. But once it leaves your head and hits the page, it becomes something different. It forces you to work out some of the fuzzy details or realize which parts won’t actually work. You can see it take shape as a real plan in the real world, and not just a castle in your mind. So if you want to move your plans forward, write them down.
And my final suggestion for today is tell a friend. This is another way of getting your plan out of your mind and into the world. If you keep it to yourself, you can find all kinds of excuses for staying in that uncomfortable comfort zone. But when you tell someone, then you’re on the hook. No one wants to be a liar, so when you tell someone else your plans, you are much more likely to follow through. And if you want to absolutely supercharge the situation, then find someone else who will do it with you. If you want to start going to the gym and you can find a buddy to go with you, then you are so much more likely to stick with it. If you want to start learning Spanish and have a friend who will speak it with you, then you will learn so much faster. Telling a friend about your plans helps; finding a friend to participate is amazing.
I want to wrap things up today with a challenge: I want you to think of one thing you’d like to improve in your life – it doesn’t have to be big or ambitious, just anything you’d like to improve – and go through the five suggestions I just shared. Start small, aim for good over perfect, choose actions that are flexible enough to deal with some changes or substitutions, write everything down, and then tell a friend what you’re planning. If you’re open to sharing and want an added layer of accountability, please send me an email to let me know your plan. I look forward to hearing from you.
Thanks,
Timothy Iseler, CFP®
Founder & Lead Advisor
Iseler Financial, LLC | Durham NC | (919) 666-7604
Iseler Financial helps creative professionals remove stress while taking control of their financial lives. We'll help identify your current strengths and weaknesses, clarify and refine your long-term goals, and prioritize decisions to improve your financial well-being now and later. Reach out today to take the first step.





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