Get Comfortable With Being Uncomfortable

The moment you're too comfortable is the moment you stop growing

If you are never uncomfortable, it means you’re not growing. There is a reason they are called growing pains. Growing means expanding your horizons and doing things that you’re not good at. It means falling, failing and making mistakes that make you feel embarrassed or judged. You can’t get better at anything if you don’t work at it. No one learns to ski without taking some bad wipeouts and tumbles. You can only ski black diamonds after you’ve fallen again and again on the greens. There is no sense of accomplishment when something comes easily. Amazing things can happen on the other side of discomfort.

Too many people suffer from inertia in their careers. They get too comfortable and stop taking risks. Then they wonder why they aren’t getting promoted. They go into cruise control and do things that are easy for them. They blame their managers for not recognizing their contributions, when in reality, they are meeting their job requirements but nothing more. They aren’t pushing themselves by taking on more responsibility to justify a promotion. In reality, these people are afraid of being pushed out of their comfort zones. People remember those who are bold not those who maintain the status quo.

Other individuals are afraid of failure so they refuse to take any risks. Taking on a new role or pivoting careers is scary because it is uncomfortable and unknown territory. We need to learn to show ourselves more self-compassion and grace when things don’t work out the way we hoped or planned. Only then will we be able to continue to embrace being uncomfortable.

Close Your Eyes and Jump

Often the hardest part about uncomfortable situations is the build up of tension. The sooner you break that tension with action, the less stressful it becomes. Once the deed is done, the tension dissipates and relief sets in. When you do this enough times, you begin to realize that the benefits of taking action far outweigh the anxiety that leads up to it. That anxiety is very real and can be paralyzing. It’s like standing at the edge of the bridge before a bungee jump or skydiving jump. It is terrifying right up until the point you jump, and once you do, it’s freeing because you can’t go back. And you are left with the exhilaration and accomplishment of overcoming that fear instead of letting it overcome you.

It doesn’t have to be bungee jumping, even asking the first question in a meeting can be scary for some. The fear of judgment from others can be even more anxiety-inducing than jumping off a bridge or plane. Until you realize that you can’t control what others think of you, and understand that they really don’t think about you as much as they think about themselves, you will never be free of that fear. But once you hear your own voice and others hear it, it becomes a lot easier to do again and again. Like anything else, getting good takes practice and repetition. Ask the first question. Volunteer to take the hard project. Step up to make the presentation at the conference. This is how you get seen, earn respect and ultimately get promoted.

Do What Needs to Be Done

Sometimes doing what needs to be done or saying what needs to be said, can mean having awkward or difficult conversations. This includes firing people at your job who aren’t performing, giving feedback to an administrator at your child’s school or confronting a neighbor who is causing problems. There are many situations in which we tend to avoid, because we are afraid of the discomfort and anxiety that comes with having these tense interactions. But like getting a vaccine or flu shot, it might hurt a little for a brief moment, but it needs to be done for the long term benefit of yourself and for others.

You will never be seen as a good leader at work if you are unable to handle letting go of a problematic employee. By delaying the inevitable, you merely destroy credibility with your other good employees, because they can’t trust you to do the right thing for the greater good. Avoiding your personal temporary discomfort leads to a lot of pain for other people, because you’re unwilling to do what needs to be done. I outline this in my previous essay about learning to embracing conflict.

If you want something, you should ask for it. You want that raise or promotion? Ask for it. You want to be on that project? Ask for it. You want to go on a date with that guy or girl? Ask for it. Yes, it might feel uncomfortable in the moment, but you owe it to yourself to know the answer. The worst that can happen is that you get a “no” but at least you will have an answer and can move on without speculating any longer. Life is too short to linger on the what ifs.

Speak Up for What is Right

It’s okay to speak up when you aren’t sure if others agree with you. There is nothing wrong with saying the unpopular or contrarian thing if you can back it up. If people are wrong, they are wrong, regardless of consensus. Many people agreeing that the wrong thing is right, doesn’t make it any more right. It might be uncomfortable at the time, but as Martin Luther King, Jr. said, “The time is always right to do what is right.” Moral action should not be delayed by convenience, fear, or seeking the “perfect” moment. You should always act with integrity, regardless of external pressures.

During the pandemic, I wrote an essay for a community that I had built over the years. It was not meant to be shared publicly. But a member of the group tweeted it to her 100,000+ followers, and I panicked. I thought I would be judged or make people angry with the essay. I wasn’t ashamed about anything I wrote in the essay, because it was all true. It was the fact that I was saying the quiet things out loud and calling out the discrimination against the Asian American community. I was afraid that there would be blowback, because I rarely saw someone with my resume take any risk by speaking up about the ugly truth. I wasn’t sure if I should take it down for damage control.

Prior to writing this essay, I had been extremely vocal in my condemnation of the murder of George Floyd. I was outspoken for the Black community on public spaces like LinkedIn and Twitter. But all of the sudden, when it was time to speak up for my own community publicly, I was scared. I was uncomfortable because I hadn’t gotten permission or seen anyone else in my position say these things openly before.

Rather than allow my discomfort or fear consume me and take down the essay, I embraced it because I knew it was the right thing to do. And because of that decision, Hyphen Capital was born and it became my life’s work. I have now invested over $35 million in Asian American founders and launched my own venture capital firm. If I had deleted the essay, none of this would have been possible.

Embracing Uncertainty

I speak to far too many people that are miserable at their current jobs, but they refuse to quit without having another job in hand. They would prefer to be miserable with a job they have, than risk not finding another one. Being comfortable with uncertainty means having the self-confidence and mindset that you can bet on yourself. Some people see the unknown as terrifying and scary like staring into a dark abyss. This is a result of a scarcity mindset that makes you live fearfully, always expecting the worst possible outcomes. Others see the unknown as an opportunity like an open field with multiple paths. This is a reflection of a growth mindset, believing in your own agency and ability to forge your own opportunities and success. For some, having the comfort and security of the bird in hand is worth far more than two right in front of them.

I know many who have fully embraced the uncertainty and changed careers. They gave up high-paying jobs that the world would label successful. My friend Abigail Hing Wen was a powerful lawyer working at Intel before becoming a bestselling young adult author and film producer/director. My friend Joyce Tang left her marketing job at Facebook to open a nationally acclaimed pastry business. Simu Liu famously got fired from his accounting job to pursue a successful career in acting. Robert Wang was a laid off software engineer who decided to solve how to make a healthier dinner, so he invented the Instant Pot. There are countless stories like these, of people who took a chance, even though they were unsure of what their future would hold on the other side. And while these are selective stories of success, I’ve spoken to those who have failed to make the pivot, and they have no regrets. You only get one life to live. Few people ever regret pursuing their dreams, but many regret never doing so.

Personality Types

I want to acknowledge that not everyone is wired to take risks. When I was working with an executive coach, I took an Enneagram personality evaluation. My Enneagram is a Type 7 or “The Enthusiast.”

The Enthusiast is characterized by a zest for life, optimism, and a drive for new, exciting experiences, seeking to avoid pain, boredom, and limitation by staying busy and planning future fun. While they are spontaneous, versatile, and good at generating ideas, they can become scattered, undisciplined, and avoid difficult emotions, potentially leading to overcommitment or escapism, but at their best, they are joyful, appreciative, and content.

As a person who is optimistic and drawn to new experiences, it is easier for me to take risks than a Type 6 or "The Skeptic.” A Type 6 prefers safety over uncertainty.

The Skeptic is characterized by a deep need for security, guidance, and support, stemming from a fear of threats in an unpredictable world, leading them to be vigilant, responsible, and loyal, yet prone to anxiety, self-doubt, and seeking reassurance, often becoming excellent troubleshooters by planning for what could go wrong.

I highly recommend speaking with an executive coach to better understand your personality type and how to deal with being uncomfortable. Everyone experiences fear and anxiety differently, and it’s important to know how you can most effectively deal with yours. Nothing is more helpful than self-awareness of how you personally are wired.

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The fear we build up in our own minds is almost always scarier than reality. We usually anchor to the worst case scenario which is the least probable one. “I will get fired from my job if I say that.” “I won’t be able to find a job if I am unemployed.” “I won’t be able to earn an income if I change careers.” “Someone will come after me if I speak out or take a stand.” We create a bogeyman in our mind that keeps us from taking risks. But everyone knows that the bigger the risk, the bigger the reward. Because when you have agency and control, you have more earning power. Starting your own business. Building your own brand. Creating and producing your own product or intellectual property. Ownership and equity is the fastest way to freedom and success.

If you were raised in a culture with an immigrant scarcity mindset, then you likely brought up to plan for and expect the worst possible scenario. You choose a career based on security and reliability. You choose the most predictable jobs that will pay the best, lawyer, doctor, engineer or finance/accounting. The problem is that now these jobs are all being replaced by AI, exactly because they are so predictable and programmable. The safest careers are no longer safe. Nothing is guaranteed and it is a myth that anything is a sure thing anymore.

What I do know is a sure thing, is that no one gets ahead without taking chances. And taking chances requires putting yourself into uncomfortable positions. The only people who succeed are the ones who stand apart from the crowd. They are the ones who get noticed because make others take notice. They speak up, they create new products or content, they take on difficult challenges.

I recently hosted a fireside chat with Julie Kim, the CEO-elect of Takeda Pharmaceuticals. She will be the first Korean American and Asian American to lead a multinational big pharma company. She said she wouldn’t have gotten to this position if she hadn’t “led from the front.” She took on managing big business units and P&Ls. She spoke at conferences. She moved around the world solving problems. None of these things were comfortable, but she did all of them. That’s what it takes to make it to the top.

Like Julie, every successful person I know has had to step out of their comfort zones and take chances. They have had to bet on themselves time and time again. But each time, it became easier, because they learned that the odds are better than they had originally assumed. If you continue to fold every hand in life, you will never have a chance at winning. You will just continue sitting on the sidelines waiting to get in the game. Stop waiting, and start making bets.