22 Ways to Try Uncomfortable New Things

SO HERE WE ARE at the beginning of a new year. The Earth has already set off on another orbit of the sun and over the next 365 days it will travel some 583 million miles. You too are beginning a journey but in your case, the goal is not to find yourself in exactly the same place come the beginning of 2026.

To be sure, you may be perfectly happy with your current circumstances and operating in a way that feels natural and easy. But we’re also guessing you yearn for just a little more, to change something about the way you typically approach business and life, to be a little bolder in the face of the opportunities the world offers.

We asked the Signs of the Times Brain Squad what most keeps them from trying new things.

When considering doing something new, important or risky, what holds you back the most?

• The fear of making a fool of yourself — 5%
• The fear of losing money — 33%
• The fear of wasting time — 26%
• The fear of being exposed to some sort of physical danger — 0%
• A general fear of the new — 7%
• Just a general lethargy that stops you taking the first step — 5%
• Other (time, how it affects team, procrastination) — 24%

You can reach the low-lying fruit with your natural abilities. But to get to the higher, riper, larger fruit “you need to add more steps to your ladder,” notes marketer and business author Roy H. Williams. “You’ve got to start doing things you’ve never done before. You have to identify your limiting beliefs and practices. You have to go outside your comfort zone.”

The problem is, change usually involves doing something that is difficult, scary or that just feels disagreeable.

As the productivity guru David Allen has noted: “What we truly need to do is often what we most feel like avoiding.” There’s usually a valid reason why we aim, aim, aim and don’t pull the trigger. Action can require engaging with uncertainty or anxiety. Change requires surrendering a sense of control and security. Then the spectre of failure lurks. And those instincts that are saying let’s not do this are the same ones that have fuelled your positive development thus far.

Fear does keep us small; growth requires discomfort. It’s something that is drilled into us from that first prick of a needle in our heel in the maternity ward, the first time we crash our tricycle or get crushed romantically as a teenager. Suffering is part of showing up for life.

In the absence of a big hand coming down from sky to push us over the edge or some external threat (a deadline, social shame, a legal requirement), change typically requires a spot of grease to get us on our way or a mental hall pass to allow us to tiptoe around the monkey-mind that puts up so much resistance to our efforts to change.

In his 2023 bestseller Atomic Habits, James Clear asserts there are Four Laws of Behavior Change: “To form good habits, make them obvious, attractive, easy, and satisfying. To break bad habits, do the opposite: make them invisible, unattractive, difficult, and unsatisfying,” he says.

To be sure, there is no avoiding some pain. There’s no escaping the grind. But how much you can put up with is up to you. To achieve anything worthwhile, including behavioral change is going to require discipline and effort. The dumbbell has to be heavy enough to make the effort uncomfortable if you are to gain anything.

Following, we provide ideas, tips and shared experiences from fellow signmakers, business experts and a range of authors in the fields from productivity to psychology to hopefully help you break free from the constraints of your comfort zone and make some progress on something you care about.

SET THE RIGHT GOALS

In line with our overall goal to act in 2025, don’t spend too much time preparing or doing the aforementioned aim, aim, aim routine. At the same time, you need to have an idea where you’re headed. Best practice for goal-setting suggests you…

• Put pen to paper. You’re more likely to follow through and while it’s not real progress, it can feel like it and get the ball rolling.
• Set ambitious goals. But be happy to settle later.
• Keeping goals vague sometimes produces higher rates of success but being specific will prevent procrastination.
• Set process goals, not outcome goals (more on this later). Pick a time and stick to it.
• The ultimate goal is to grow in some area of your business or personal life, not turn your daily existence into a grind. Think about how to make achieving your goals and making progress fun.

MAKE A DECLARATION

Shout it from the rooftops. Establishing accountability with a friend, mentor or even a business magazine can be motivating, even if it’s a little negative, exploiting your fear of having to confess that you never got around to doing what you said you would. If you’d rather not pester family and friends with your goals, goal-publicizing websites like Home allow you to enlist random internet strangers to act as witness to your vows to change.

BURN YOUR BOATS

Taking an action you can’t undo can be a radical but often a better strategy than keeping your options open. As the writer David Mamet once put it, “Those with something to fall back on invariably fall back on it.” In life, as in a fight, the advantage often goes to the one with nothing left to lose.

DEVELOP A GROWTH MINDSET

We know you’ve heard it before, possibly repackaged as “failing forward” or something similar, but developing a growth mindset, where you view challenges as opportunities to learn rather than as obstacles, is incredibly useful. In The Lean Startup, Eric Ries notes that “little bets” or experiments are critical to moving a business forward in a safe fashion. “If you cannot fail, you cannot learn.” Getting it wrong, helps you get it right.

CONFRONT YOUR FEARS

Alternatively, try gaining serenity by actively confronting the experience of failure. Try keeping a notebook and for a week, write down everything you feared could go wrong about anything. You’ll likely discover just how off target your fears typically are.

MOTIVATION IS FOR AMATEURS

Your mind will prepare a surprising number of hurdles and traps to prevent you from getting this thing done. It will insist you need to be in the right state of mind, that your life has been arranged sufficiently to accommodate this important task, with long stretches of uninterrupted time in which to do it. End result? Important stuff doesn’t get done. But the fact is, you don’t need to feel good to get going. It’s often the other way around. In the late 1970’s, “behavioral activation” research showed that action doesn’t depend on motivation; instead, motivation follows action — and therefore one key to boosting mood is to take the small steps simply to get started.

THE TWO-MINUTE RULE

Make the first few milestones easy. James Clear says that when starting a new habit, it should take less than two minutes to do to help overcome inertia. “(The rule) says just take whatever habit you’re trying to build and you scale it down to something that takes two minutes or less to do. So “read 30 books a year” becomes “read one page” or “meditate five days a week for 30 minutes” becomes “meditate for 60 seconds.” You’re just trying to master the art of showing up. A habit must be established before it can be improved.

TRACK YOUR PROGRESS

Track your accomplishments on a chart. Do anything so that you can see progress because as Harvard Business School professors Teresa Amabile and Steven Kramer showed in their book Progress Principle, nothing motivates an individual more than seeing progress on a meaningful task. And if you fall off? Get back on the horse with a low target. “Really, all you need to do is focus on having five good minutes. You can do a lot with five good minutes.” says Clear.

MAKE IT ENJOYABLE

“Come up with three new sales lines every day” won’t work unless you get excited about devising sales approaches. And no improvement regime will last long if you don’t at least slightly enjoy what you’re doing. The habits that stick tend to be those that are fun — and indeed you can turn something you like doing into a chore if you add enough compulsion. Pursue your goal or new habit with a friend or spouse. Gamify it. Make it a fun competition. And don’t forget to celebrate, even the smallest wins.

REWARD YOURSELF

Completion of your new habit should be a nice reward in itself, but it doesn’t hurt to add another layer to get you across the finish line each day. Maybe you get to have your favorite type of coffee or healthy snack after that, or maybe you get to watch the highlights of the weekend game on YouTube or take a walk in the woods. “So find some way to add some additional positive emotions to the experience because if you feel good about it, you’re going to want to repeat it,” Clear told the Brene Brown podcast.

EMBRACE THE PROCESS

You can talk lofty principles all you like, but it’s structure — designating time for something, then doing it — that gets things done. Set process goals, not outcome goals; think quantity, not quality: “make four phone calls per day” not “build a killer business network.” One of the key points in Atomic Habits, says Clear, is that “you don’t rise to the level of your goals, you fall to the level of your systems.” It sounds pretty dull. But that’s exactly as it should be: It makes behavior change non-intimidating, and thus it makes behavior change actually likely to happen.

IDENTITY

Focus on the type of person you want to become rather than solely on your goals. By shifting the focus to identity, habits become more sustainable, says Clear. “Your current behaviors are simply a reflection of your current identity. … To change your behavior for good, you need to start believing new things about yourself. You need to build identity-based habits.”

PHYSICAL ENVIRONMENT MATTERS

Humans are often creatures of habit, heavily influenced by our surroundings. Context dictates our behaviors — larger plates lead to greater food consumption, kindness begets kindness, our clothes influence how we act. Eric Barker from the productivity website Barking Up the Wrong Tree advises manipulating your environment to make positive behaviors easier and negative ones harder. He suggests evaluating your spaces — office, kitchen, bedroom — and asking, “What behaviors are encouraged here?” While making one or two adjustments may not drastically change your life, implementing a dozen or more changes across your environments can create a supportive atmosphere for building desired habits.

SOCIAL ENVIRONMENT MATTERS

Those around you affect more of your behavior than you think. Poor fitness, car purchases, lateness, having children, charitable contributions, divorce and stupidity are all — in the words of social scientists — contagious. It’s something you’ve known since junior high: Social norms and peer pressure are incredibly powerful, perhaps the most powerful and direct way to influence behavior change. People want to fit in, belong, be part of the tribe. The trick, then, is to surround yourself with people where your desired behavior is the normal behavior. “When you want to create a habit, think of who already does it, interact with them, and ‘catch’ their habit,” writes Joshua Spodek, a lecturer at Columbia Business School and columnist for Everything You Need to Know to Start and Grow Your Business.

BUILD AN ON-RAMP

In Deep Work, author Cal Newport emphasizes the importance of establishing a ritual as part of your preparations to accomplish important work, claiming such rituals reduce the mental resistance to getting started on a task, and to signal to your brain that it’s time to focus. Whether it’s a ritual that includes doing laps of your office and shop or greasing the wheels by removing every possible mental hurdle, the goal is the same: to build an on-ramp that once you step on to it, will launch you inexorably into a day of action.

REFLECT AND REVIEW

To keep improving over time, you need feedback. Follow the advice of time-management experts by conducting a “weekly review” of your progress. This practice helps identify areas for improvement and reinforces your commitment to your goals. Pete Drucker, author of The Effective Executive, was an advocate of such regular assessments: “Look for patterns in what you’re seeing: What results are you skilled at generating? What abilities do you need to enhance in order to get the results you want? What unproductive habits are preventing you from creating the outcomes you desire? In identifying opportunities for improvement, don’t waste time cultivating skill areas where you have little competence. Instead, concentrate on — and build on — your strengths.”

AT THE BOTTOM
IS DISCIPLINE

You may have noticed a pattern to many of the tips cited here. Make it easy to do. Make it easy to show up. And make it fun, or at least satisfying. They are all valid strategies, but there is also no escaping the fact that behavior change or getting things done takes some grit. The bottom layer of any pyramid of success is discipline, and it can be imposed from the outside or inside. Faced with moments requiring that grit, standard psychological advice is try one (or all) of these tactics:

• Recognize that the event isn’t causing your dread; your interpretation of the event as dreadful is.
• Repeat a short, somewhat positive statement about the event, such as, “It wasn’t that bad in the past.”
• Realize the event is transient. It won’t last forever.

CULTIVATE PATIENCE

Progress toward meaningful change often appears slow at first. Understanding this can help maintain motivation during periods where results are not immediately visible. “Cultivating patience and allowing for setbacks as part of the learning process is essential for long-term success,’” says Clear, who calls these phases “The Plateau of Latent Potential.”

PLAY WITH FRICTION

It’s tempting to view your habits as a matter of self-control, but usually bad habits happen for exactly the opposite reason. When we’re not making deliberate choices, we fall back on whatever feels the most comfortable or convenient. Thus, one of the best ways to break a bad habit is to make it less convenient by adding some friction. As advice site Barking Up the Wrong Tree explains, even adding an extra 20 seconds to your habit can give you enough time to break the cycle. Take the batteries out of your remote if you want to stop watching so much TV.

MAKE THE MOST
OF YOUR GUILT

Resistance, as we noted earlier, serves as a signal: It tends to attach itself to stuff that really matters. Attack your most guilt-inducing tasks and you may find, without intending it, that you’ve attacked the most important ones too. That’s the thinking behind a Guilt Hour, as championed by productivity types. Schedule one hour a week for your team to sit down and nominate a task they feel guilty about not accomplishing and then give them the rest of the hour to get it done, or least make a significant start. The public confession aspect — along with the social accountability — is a key part, as is the scheduling of it.

FORGIVE YOURSELF

According to some estimates, 80% of the chatter in your head is negative. It is something to watch out for when you’re needlessly hard on yourself. “Self-blame shuts down learning centers in the brain,” says Tara Brach, a clinical psychologist and author of Radical Acceptance. “Actively offer yourself forgiveness by, for example, whispering ‘forgiven’ or putting a hand on your heart,” she says, adding that research shows self-compassion is related to the pursuit of important goals, lower procrastination and less fear of failure.

SWITCH TO YOUR
OWN CALENDAR

Despite the “new year, fresh start” premise of this story, nothing says you need to be bound by the traditional calendar when setting goals for change. For consultants Brian Moran and Michael Lennington, thinking of life in 365-day units isn’t only arbitrary, it’s detrimental. A year’s too big to get your head around, they argue in The 12-Week Year, and there’s too much unpredictability involved in planning for 10 or 11 months in the future. Jettison “annualised thinking,” Moran and Lennington insist. Their proposed alternative is to think of each 12 weeks as a stand-alone “year” — a stretch long enough to make significant progress on a few fronts, yet short enough to stay focused.