I can almost recite word for word a familiar question I get during Q&A sessions after I present.

“How do I get my team to come out of their shells to be more courageous at work?”

There’s no doubt that professionals want to take worthwhile risks in the workplace. Part one of this series explored specific actions they want to pursue. But if you ask some managers, they’ll likely tell you that they can’t crack the code on getting these team members to move past go.

Managers have more pressure on them than ever to produce efficient results, show value that can’t be duplicated by artificial intelligence and build skills among team members that help position their organizations for success in the future.  And, their success as managers is inextricably tied to amplifying their team’s ability to perform to their potential.

I asked over 210 professionals from a range of industries — from finance to real estate to youth development to science  —  in an open-ended survey, what was stopping them from acting courageously at work. And, their responses revealed four clear answers.

This is the second installment of a three-part series that illuminates what risks employees want to take, what stops them from taking them and what they can do to move forward to courageously step into their potential.

Lack of Support

About 14.2% of respondents cited a lack of support as the barrier blocking the way to acting courageously at work. For many, a lack of support meant feeling unheard by their managers. Respondents reported that “management has a history of not taking my suggestions” and that “it’s hard to support the little guy when management doesn’t want to hear it.” Others noted that they had previously stepped out of their comfort zone in a move towards courage but got shut down, which, as a result, shut down their desire to try again. “When I have asked before, I got a chuckle, and they walked away,” one respondent said. Another responded, with a palpable sense of exasperation, that “it would be easier to find another job than to push my ideas.”

When professionals feel like their unique ideas and perspectives go unheard, unnoticed and undervalued, they stop trying. They stop contributing. Managers who most need their team members to speak up and step up to help grow the business can often be the same managers who — due to a lack of support — deter them from being visible and vocal. And, as a result, professionals become disengaged and less productive, both of which can adversely impact the organization’s culture and bottom line. 

Fear of Rejection

Another 13.7% of survey participants reported that a fear of rejection kept them from acting courageously at work. Respondents revealed that they didn’t want others to “perceive I’m the problem” or that they feared “rejection of my ideas.” I’ve often talked about fear of rejection in my work, and what I’ve come to understand (and written about before) is that no one wants to lose access to the inner circle or opportunities to lead projects and be promoted. So, we learn to demonstrate pro-social behaviors so we can go along and get along with the group. So much of our brains are devoted to social interaction. Overcoming the fear of rejection requires individual effort and intention. It also requires organizations to create the conditions where professionals feel safe — where they don’t feel like they’ll be retaliated against for bringing their ideas, concerns and true selves forward.

Fear of the Unknown

About 12.2% of respondents wrote that a fear of not knowing keeps them from acting courageously at work. Survey participants in this group used words and phrases like “uncertainty,” “fear of the unknown” and “might not be able to” in their responses. It’s quite natural for anyone to want to feel a sense of certainty before diving into a new project or experience. But, risk, inherently, carries a quality of not knowing with it. This means, professionals who are unable or unwilling to engage with the unknown are professionals who are unable or unwilling to take risks. And, when professionals aren’t taking risks, they’re not discovering how reliable their skills are and what they’re capable of.  This untapped potential, undoubtedly, impacts how far an organization can go and grow.

Fear of Failure

Professionals who responded to the survey — 10.3% of them — identified fear of failure as their challenge to acting courageously at work. They revealed that they “don’t want to disappoint,” “get it wrong” or “make mistakes.” One respondent said they were “worried I might be given the chance, then fail.” When professionals feel like failing isn’t well tolerated within their organizations or on their teams, they’ll do whatever is necessary to protect themselves from it. Often that means, they won’t step outside their comfort zones to own their brilliance. As I have written before, organizations stacked with professionals who are afraid of failing are fundamentally restricted from reaching their highest level of excellence. (The professionals themselves are, too.)

These four responses make up about half of the reported reasons why professionals don’t take worthwhile risks at work. In the last installment of this series, I’ll dive into what organizations can do to create a courage-ready culture where their people are equipped to courageously speak up, step up and show up in the workplace. 

You could focus your ambition on managing a new project, expanding your influence or improving time management. The goals that deserve critical attention, though, are the ones that will help you consistently develop into a courageous leader — a leader who effectively guides themself or others to willingly direct their gifts and skills to the organization’s mission in the face of challenges and risks.

Now more than ever, organizations need leaders who have the adaptive and cognitive skills that can help position their businesses for the future. They need leaders who possess interpersonal and emotional skills that will allow them to foster inclusive relationships among cross-functional teams and help younger leaders thrive in a constantly shifting (corporate and non-profit) world.   

So, this year when you dust off your previous performance review to reassess old workplace goals and prepare yourself to select new ones, be sure to prioritize pursuits that will help you flex your courage muscle.

To help you get started, here are three valuable workplace goals you can establish and practice every day to help you navigate through uncertainty and lead courageously.

Take A Risk, Every Day. 

On the surface, setting a goal to take one risk each day may not seem like a serious or impressive aim. But, don’t be deceived. It is a powerful, foundational action you can take to propel you down the path of becoming a better leader. Risks are central to courage, making risk-taking central to courageous leadership. Risks are defined as situations involving exposure to danger or difficulty. And, those difficulties can manifest in the workplace in a moral, social or psychological capacity. Since we’re biologically wired to avoid danger, we can easily register risk-taking as antagonistic and maybe even unnecessary. But, taking risks also paves the way to growth. In fact, psychologist Abraham Maslow believed that people who actualize their potential make risk-taking routine. They choose growth over fear consistently.

Being a courageous leader means choosing growth over fear consistently. When you make a habit out of taking risks, you get consistent practice in acknowledging, settling into and taming discomfort. The leader who hasn’t practiced being uncomfortable may find current workplace challenges — that call for radical innovation, company culture overhauls and up-skilling employees — too overwhelming to address. That leader may double down on the status quo to avoid failure or keep quiet to circumvent humiliation. But, when you’ve built up the ability to be uncomfortable, you better position yourself to instigate change. 

Your commitment to taking risks every day is mutually beneficial for you and your employer. You walk away with self-discovery, improved skills and expansion of your comfort zone. Your employer increases its ability to fail fast, innovate and transform itself into a courageous organization.

The professional risks you take on a daily basis don’t need to be blockbusters. In fact, you should start small. Smaller risks provide opportunities to flirt with the unknown, interpret emotions, and evaluate outcomes in low-stakes environments.  They help you navigate within uncertainty without exposure to grave danger. Having success with small risks allows you to build upon those successes with larger risks involving larger consequences (and rewards). 

I have found that there are two main ways you can fulfill a goal of one risk a day. You can move through your day with a heightened awareness of what causes you discomfort and choose in the moment to take a risk. Or, you can plan your risks out each week. If you have a larger goal that you’ve set, you can identify smaller risks within the goal to tackle each day. 

Ask More Questions, Every Day. 

Curiosity has been hailed on list after list as one of the most critical qualities a leader should possess. It is a strong desire to know or learn something.  And, in today’s workplace and economy, there’s a lot to learn. Employers need leaders who ask more questions. 

You may think that this is an easy enough action and doesn’t require being made into a workplace goal. But, think again. Your brain is wired to make assumptions — to settle on what you think you already know. A common assumption you can make in the workplace is to think that things really are the way you see them — that there’s no room for growth or that the process will never change. Without asking questions, this assumption could prevent you from discovering creative solutions to an underlying problem. Another assumption you may hold is that the way you feel about someone is the way they actually are. This assumption, left unchecked, could lead you to misunderstand your teammates and complicate collaboration. You might even assume that you are smarter than someone who doesn’t share your point of view. Without probing for information, this assumption could prevent you from folding in other people’s perspectives and gaining a better world view of a challenge.  

Making assumptions is a way for your brain to conserve energy because assumptions offer an efficient way to process your environment.  But, to become a better, more courageous leader, you’ll need to challenge your assumption by developing a rhythm of asking questions. Curiosity fosters openness, creativity, growth, achievement and learning. On top of that, asking questions — for clarification or discovery — creates an entry point into intimidating conversations that you may have otherwise avoided. Your workplace goal to be more curious has lasting benefits for your company, too, because it invites awareness of external pressures, creative problem-solving, high-speed adaptability and better decision-making. 

There’s no right or wrong process for asking more questions. You do, however, want to be mindful of the energy you attach to the questions you ask out loud, in front of people. A line of inquiry that comes in an overly combative, intrusive or trivializing way may unintentionally deplete this goal from the goodness it offers. 

Make Meaningful Connections, Every Day. 

In an increasingly electronically connected workplace, personal relationships are essential. How often do you shoot off a text, email or Slack message to a teammate without considering whether you are connecting personally? 

Setting an everyday workplace goal to make meaningful connections with colleagues can help you build critical relationships that cultivate trust, respect and compassion — even as you challenge each other. What qualifies as meaningful? Experiences, conversations or other exchanges that provide value and have meaning to both people. If fact, meaningful connections often include elements of vulnerability because when you really connect, you expose your need to be seen, heard and accepted. That, in itself, is an act of personal courage. On the other hand, connections that are transactional or asymmetric (beneficial to only one person) can come off as superficial and dishonest.  It is especially important to be vigilant over the execution of this goal to ensure attempts to connect don’t turn into empty efforts to check a box. 

In my experience as a manager, I’ve seen that a personal connection goal can benefit teammates who have a fast-paced, competitive work-style and are more focused on projects than people. This type of goal can also help more passive employees prioritize relationship-building in a way that feels honest to them. A workplace goal focused on connection can assist you in showing up in relationships more powerfully and intentionally and help people to believe in you. In addition, your ability as a leader to better connect with your team helps your company better address the needs of and care for its people.

Setting a goal to make a meaningful connection every day doesn’t mean that you need to scheduled daily video calls with a different team member to get face time or ask them about their weekend. The only shift you may need to make is to purposefully elevate and personalize the conversations you are already having.

The Bottom Line

There are an endless amount of workplace goals you could set for yourself in the next month or year. But, the ones you should prioritize are those that will help you become a more courageous leader.

If you’d like to work with me one-on-one to save time and energy on the path to becoming a more courageous leader, let’s chat about coaching.

When it comes to courage, we cannot separate possibility from risk.

A listener called into The Courage Hotline podcast and asked me how stand in her courage — how to stand firm in saying how she wanted to represent herself in the world — without coming across to others as cocky.

The last part of her question engaged all of my senses … and my attitude, too.

Don’t worry about what other people think. Worrying about other people will have you out here playing small, staying stagnant, dismissing your own progress and ambition, and diminishing your own skills. Worrying about other people will have you taking away energy that is meant for developing your own potential and giving it away to people who (let’s be honest) are not really worried about you. 

I said those words to her on the episode while I simultaneously side-eyed all of her haters.

Then, I got serious to help her recognize she was trying to employ a courage hack that never ever works.

Courage Hack Not To Try

She was doing something that a lot of people try to do with courage, and that is: take the good that comes with courage and leave behind whatever is less-than-ideal. We try to take possibility with us and leave potential problems where they are.

“I want to achieve this really important personal goal that will shape how I show up in the world, but I don’t want to deal with a tinge of resistance.”

Many of us, like the caller, want to conjure the courage to be who we are, but we don’t want people to roll their eyes at us for being who we are. We want to have a hard conversation to gain the respect we deserve, but we don’t want the conversation to end with tension. We want to throw our hat in the ring for a personal or professional opportunity, but we don’t want to be rejected.

Spoiler alert: That’s not how courage works. THAT would be too easy (and quite honesty, too boring). 

If courage came with a guarantee that all would go as planned, it would be called by a different name and used like the toilet (which is all the time).

Try This Instead

So, the question becomes, what can you do to ready yourself for the not-so-warm-and-fuzzy outcomes that could accompany courageous action? The answer is not to try to hack courage. Instead it is to clarify, prepare and take responsibility.

When it comes to courage, we cannot separate possibility from risk. Trying to do so is futile. Courage, by nature, is risky. This means if there was no risk to the actor, there would be no need for courage.

1. Clarify potential outcomes. What are the less-than-ideal outcomes you want to avoid so badly? Is it failure, rejection or judgment? Clarify them, so you can calculate them. Calculate them so you can control them (as best you can).
2. Prepare for potential outcomes.  What if you were to fail? Or be judged? How would you prepare for those outcomes? How would you come back from a conversation that ended with tension? Anticipate outcomes, especially the ones you want to avoid, and consider how yo would deal with them if they were to happen.
3. Take responsibility for potential outcomes. Whatever happens, happens because we made a decision to move forward with courage. We are responsible for any outcome. The quicker we accept responsibility, the quicker we can evaluate results, learn from them and build on them.

This episode ends with the segment Courage Over Everything, in which I drop one final gem on courage before signing off.

If you’re feeling this episode, don’t forget to rate, review,  subscribe and share. If you’ve got feedback or suggestions, drop a line at info@candacedoby.com. Need help? Submit your question to the show.

Mentions in This Episode:

MJ Rodriguez – is an American transgender actress and singer.

Dominique Jackson – is a Tobagonian-American transgender actress, author, model, and reality television personality.

Pose – is an American drama television series about New York City’s African-American and Latino LGBTQ and gender-non conforming drag ball culture scene in the 1980s, early 1990s in the second season, and the mid-to-late 1990s in the third season.

Transplaining – is an organization working to create a safe(r) world for transgender and gender non-conforming youth and adults through education, community conversations and as much empathy as it can safely exert.

This episode features a new segment, Courage Over Everything. In this segment, I drop one final gem on courage before signing off.

If you’re feeling this episode, don’t forget to rate, review,  subscribe and share. If you’ve got feedback or suggestions, drop a line  at info@candacedoby.com. Need help? Submit your question to the show.

If you’re feeling this episode, don’t forget to rate, review,  subscribe and share. If you’ve got feedback or suggestions, drop a line  at info@candacedoby.com. Need help? Submit your question to the show.

Sponsors:

Concept Citron: Thank you to Concept Citron for supporting The  Courage Hotline. Concept Citron is a design agency in Quebec Canada that  offers playful designs for branding, logos, website design,  illustrations and much more. Visit Concept Citron to get your design project started today.

I also dig into my courage toolbox to help another challenged caller determine if he should tell his best friend that he loves him and ask for more from the friendship.  He wants to be honest but also doesn’t want his friend to get scared and leave.

If you’re feeling this episode, don’t forget to rate, review, subscribe and share. If you’ve got feedback or suggestions, drop a line at info@candacedoby.com. Need help? Submit your question to the show.

Sponsors:

Concept Citron: Thank you to Concept Citron for supporting The Courage Hotline. Concept Citron is a design agency in Quebec Canada that offers playful designs for branding, logos, website design, illustrations and much more. Visit Concept Citron to get your design project started today.

That recognition led me to the worldwide bestselling book, Against the Gods: The Remarkable Story of Risk by Peter L. Bernstein. In reading the book, I uncovered three reasons why our emotions make us miscalculate risks, and I considered how those miscalculations can slow us down from taking courageous actions that will help us grow personally and professionally.

Emotions cloud judgement.

Making good decisions about which risks to take requires rational thinking, which is the ability to consider and analyze information relevant to a particular situation.  Against the Gods highlights the idea that emotions at full tilt can make it difficult for us to “question the relevance of the assumptions” we hold and use to support the decisions we make.  When our emotions inhibit us from questioning our assumptions, we can get stuck in a loop of emotional reasoning where we assume (there’s that word again) certain emotions reflect the way things really are … when, in reality, they are completely different.  This doesn’t mean that emotions can’t be helpful in directing our energy to specific areas that need attention. However,  when we let our emotions run wild, they can cloud our judgment and weaken our ability to inquire, think critically and seek out the truth.

On a visit to Rome, Italy, I was responsible for chaperoning a group of teenage girls from the Vatican to the Colosseum. I was instructed by our seasoned guide to take the subway to get there. But, I was extremely hot, sweaty and tired from the overwhelming heat of the day. And, the subway seemed miles away. A local sensed my confusion and suggested that we could take the bus, instead, which would dropped us off close to the Colosseum. And, lucky for us, the stop was across the street. I decided we would ride the bus.

What I didn’t ask the local, though, was how often the bus ran and exactly how far we would be from the Colosseum at drop off. We waited for the bus for what seemed like an hour and then had to walk a mile to get to the gate. We almost missed our timed entry into the Colosseum … because of my feelings about the heat.

So, how do we temper emotions to help our rational brain emerge when we need to make a difficult decision? One solution is to employ a tool many psychologists have used to help their clients untangle themselves from the web of irrationality that emotions often get them into: emotional distancing.

Emotional distancing is the process of  removing yourself psychologically from the center of a situation where emotions can gain intensity and repositioning yourself as an observer on the outside edge of the situation.  Instead of thinking of what you should do in a situation, emotional distancing may lead you to consider what you would coach your best friend to do in the same situation. 

Creating emotional distance between you and the situation can help you alleviate pressure, regain self-control and fire up your rational brain.

But, there’s another, more specific, way our emotions can get in the way of making rational decisions in the middle of risky or challenging situations.

Fear of loss constrains choices.

Amos Tversky, a leading researcher in human cognition who is quoted often in Against the Gods observed that people are not risk-averse, they are loss-averse.

“It’s not so much that people hate uncertainty — but rather they hate losing.”

This couldn’t be more true with one of my coaching clients who wanted to ask her boss for a well-deserved raise. In the beginning of our work together, a large segment of attention was dedicated to navigating through the risk of losing her job and influence as a result of her request. That’s what concerned her the most.

The fear of loss can cause us to overly (and sometimes irrationally) focus and rely on a small segment of information in a large consideration set to protect ourselves from pain. My client, in an effort to circumvent the consequences of loss, couldn’t recognize what she would potentially gain from honoring herself and her talent appropriately by requesting additional compensation — that, in the end, could come in different forms than money.
The shift in mental perception from losses to gains is a critical one.

According to research included in the book, “losses will always loom larger than gains.”  It’s why we focus on negative potential outcomes more than desired ones and also why we are likely to experience intense risk-aversion in many decision making processes. 

So, it becomes considerably important to us to put in the mental work to transform the perception of risk from chance of loss into opportunity for gain. In the end, we are not helpless beings irrevocably controlled by fate but rather empowered people who can make a choice within a set of opportunities.

Overestimation of the past and the present distorts reality.

An important, and final, way emotions can hijack our ability to appropriately calculate risks has to do with how much value we place on past and present experiences.

Against the Gods highlights the importance of sampling to risk-taking and says that, “we constantly use samples of the present and the past to guess about the future.”

To be fair, whatever data samples we choose to analyze within our decisions are incapable of representing the whole of reality.

But, when those samples are selected by emotion rather than relevance, things can get even trickier. Our emotions, according to the book, often push us to “seek shelter from unpleasant surprises.”

Overemphasizing emotionally-charged experiences from the past and present can distort reality, lead to unwise decisions and flawed assessments, and compel us to resort to dodges that, ultimately, disrespect rational thinking.

When dealing with uncertainty, which is an inherent part of risk-taking, we often demonstrate patterns of irrationality, inconsistency and incompetence that lead us to miscalculate risks.

So, how can we get better at selecting appropriate samples that will help us make rational decisions and not miscalculate risks? We can return to the first point in this post for help.

We need to “question the relevance of the assumptions  that support the procedure.”

This may be one of the most important takeaways from Against the Gods: The Remarkable Story of Risk.

The willingness to take risks is important to growth on all levels, but the road to risk-taking can be clouded with emotional roadblocks that lead to irrationality and inconsistency in our decision making. To prevent our emotions from taking us down a path of unwise decisions and faulty evaluations, it is important for us to establish a pattern of inquiry that helps us assess the relevance of assumptions we make within our decisions and to keep our emotions in check.

Rollercoasters may come to mind when you think about wild rides. Maybe even a basketball game that boils down to the final second. But, an entire calendar year? No one imagined 2020 would be as much of a nail biter as it was. It is being called the year of the pivot — the year that pushed people to about-face on previous plans, perspectives and priorities.

It challenged people to call on personal courage to do hard things. I wanted to know what some of those hard things were. So, in October, I began hosting a series on Instagram Live called Courage With Friends. I set up short conversations with girlfriends from child- and adulthood to hear about their most courageous moments of the year. 

And, what I learned from this group of dynamic, young professional women is that 2020 was the unexpected, yet perfect, set up for them to turn inward to better understand and be themselves. Below are powerful excerpts from their interviews, which have been edited for clarity.

There was plenty of goodness in each interview, so it was difficult to pull out one quote to share. If you missed the conversations live or want to hear them again, you can find the recordings on my Instagram feed. 

As you read below or listen to the interviews, consider this for yourself:

How did you act courageously in 2020?

Martice Sutton
Founder – Girls Going Global
Decided to take a career break from an organization she founded

“I was dealing with racial trauma, economic trauma, professional trauma and personal trauma in regards to a romantic heartbreak, and they affected how I was moving about the world. [I had to have] a hard conversation with myself and do a hard assessment of where I was, where I was looking to go and how I was genuinely feeling … I am making a decision to save my life. And, because of that I cannot allow myself to get too entangled on what I’m missing out on … Sometimes you have to put everything on hold to save yourself.
Watch the interview >>>

Lashawn Gee
Mindset Coach – ElleGee Wellness Solutions
Became a full-time entrepreneur full-time

“I thought about this to myself: did I make the right decision? The one thing that came back to me was … but you did it. I could worry about all of the things that didn’t happen the way that I wanted to have them happen. I can pine and sulk over the things that I thought I should have right now and don’t. But the fact is [entrepreneurship] has up-leveled me to ignite disciple even more … to take my business far beyond what I thought. Even though it’s not right here in front of me, the fact that I know it’s possible and the fact that I embrace that it is possible, puts me out here to do the work even more. 
Watch the interview >>>

Shannon Burns
Non-Profit Director of Education & Solopreneur – Soul and Ginger
Started saying “yes” to herself after breaking down at work

“I had a pivotal moment. It was in June of this year. My job is pretty stressful; I work for a non-profit that is in the business of helping people prepare for home-ownership … due to Covid we received funding to help people who needed help with rent and mortgages, so I was on all of these teams and was just overwhelmed. I had a mini-meltdown before I broke down … and my soul had to release. Sometimes your soul shakes you awake and says, “hey, you need to focus on you.” 
Watch the interview >>>

Elandria Charles
Non-Profit Leader
Decided that “I am enough” after breaking down at work

“In March, I had just come back to work from maternity leave and was going to prove to myself that I could come back and be the boss I was before I left … I was working myself like crazy. I had no boundaries and just felt really empty. Months later, I woke up one morning and had four meetings on my calendar. I got off the second meeting and was like, ‘I can’t do this anymore.’ I literally had nothing else to give. I realized I was putting a lot of expectations on myself.  If I’m being really honest with myself, I think it’s connected to … being in a white dominant society that is based on perfectionism and productivity. So, I think I’m putting myself under immense pressure and expectation that said my value equals my productivity. What this pandemic has shown me is that I have to stripe off all the facades. The pandemic has helped me to stop trying to pretend to be what other people want me to be and truly embrace me. I had to decide that I am valuable just by being in the room. If I say something or present something, that’s icing on the cake.” 
Watch the interview >>>

Constance Jones
CEO, Noble Network of Charter Schools
Learned how to be alone

“I am a big extrovert … I’m the type of person that would on the weekend have the brunches lined up, church lined up, evening dinners lined up. But, the pandemic forced me to learn how to be alone. I don’t have a partner or any pets. I had used being around people and social situations as a way to distract myself from real big problems in my life that quite frankly I just needed to sit with and deal with. In the last four years, my father died, I got a divorce, my dog of 16 years died, and I became a CEO in a transition that was unplanned and had to help the organization evolve quickly. The pandemic forced me to get on my couch and deal with sadness, trauma, even anger. I’ve learned to be at peace with myself.  I’ve learned to let all of these superficial, artificial things and people who don’t matter go. We need to normalize failure because it’s part of us becoming better.”
Watch the interview >>>

Yolanda Christopher
Leadership Coach, Yolanda Christopher
Dropped the illusion of control in her life

“Everything seemed to be fine because I was controlling things. I was a stay-at-home mom at the time, and I was doing all the things. I was making all of the meals from scratch, the house was clean, my kids and I were doing crafts and science experiments. There was a lot of control happening in what I was doing because of the outcome I wanted for their lives and mine as a wife in the household. And I had this realization that I was controlling my happiness by trying to control all of these things. It’s scary giving up control, but dropping the control has brought me back to the things I want versus the things that I think other people need.” 
Watch the interview >>>

Christina Doby
Surgical Services Registered Nurse, Level 1 Trauma Unit
Worked in health care during COVID

“Being a registered nurse at a level 1 trauma center in the region, you don’t  know what’s going to roll through your door in the next two seconds. We get the people who are gun victims, stab victims.  The stress of the unknown is already there, but with Covid on top of that, it compounds the stress. I have to wonder if my patients who come in also have Covid. As a nurse, I have to toe the line between being caring and careful. I think the pandemic has helped people put priorities in order. It has helped me, too, to understand that sometimes things are not that deep. I’m not going to yell about the shoe in the middle of the kitchen floor because it’s not going to matter in six months. Time is so precious. We can not get it back. We have to focus on things that matter.”
Watch the interview >>> 

When you look back on your 2020, what what your most impactful or biggest moment of courage?

You want to speak up with an unpopular opinion in a meeting of like minds and bring your whole, real self to every personal and professional space you occupy. You wish to have hard conversations about racial and gender equity and ask for a raise (yes, during a pandemic). You desire to follow a path that no one else seems to be on.

But, here’s the problem. You recognize the perilousness of these actions and find yourself crunched between a space of motivation and immobility. You are confused about whether to listen to the voice of fear, courage or … your mother. So, the question that keeps looping in your head is, “how do I know when I’m ready to take a risk?”

There’s no way to have full certainty in answering until you take the risk, but there are means to getting clearer. Here are three.

 
You understand the risk from multiple angles. 

If you’re like most people, your mind wastes no time helping you see how horrid things could end up from taking a risk. You could lose friends, social status and financial stability. You could fail and feel judged. You could get bruised, physically or psychologically.  These are often the persistent, and sometimes debilitating, thoughts that prevent us from moving beyond the starting line of our most meaningful pursuits. We get scared because of what we imagine could happen.

But, there’s another, often ignored, side of risk that requires the same level of consideration. And, that’s the risk of not taking action. When you dedicate equal mental energy to understanding the risk of not asking for the raise or speaking up in a meeting, you create important space for perspective. And, here’s what you’ll learn. The downside of this risk puts your growth, development, success and happiness at stake. John F Kennedy acknowledged this when he said, “There are risks and costs to action. But they are far less than the long range risks of comfortable inaction.”

When you’ve evaluated both sides of a risk, and you conclude that the risk of not taking the action is greater than the risk of taking it, you’ve moved a step closer to readying yourself for risk-taking. 

You trust your ability to be uncomfortable.

Exposure to danger, which is an inherent part of risk-taking, often brings with it a feeling of discomfort. Butterfly swarms in the gut. Heart palpitations. Unshakeable paranoia that everyone around is serving up their fiercest side-eye. It’s enough to make you want to flee as fast as you can. Going toe-to-toe with risk, then, requires settling into discomfort.

You better position yourself to take risks and persevere through them when can inhabit your discomfort This means you can successfully occupy uneasiness — sit with it — until it starts to feel less threatening. This skill is built up through repetition and encouragement. 

You trust your ability to figure it out.

What if the most unsavory potential outcomes from taking a risk became reality? Let’s say you asked for a raise and ended up getting fired. Maybe you had a conversation with family about race and got uninvited to Thanksgiving dinner. Or, you changed your major and lost tuition assistance from your parents.

A telling way for you to know if you’re ready to take a risk is to think of a worst-case outcome and ask yourself if you believe in your ability to work through it. “Events are events, situations are situations. It’s what we make of them that determines how we react and what we do next,” says author and Bob Taibbi. 

The invaluable ability of figuring it out requires a level of optimism, rationality and reliance on past experiences where you dusted yourself off and kept pushing. 

The bottom line

You’re unlikely to have absolute certainty about whether you’re ready to take a risk … until you take it. But, you can more fully evaluate risk and mine your skills to help you clarify your readiness. Ensure that you understand risk of action and inaction when you’re engaged in the process of evaluation. Without looking at both sides, you prevent yourself seeing a whole picture.

Then, assess whether you trust your ability to be uncomfortable. Do you have reliable experience sitting, standing and settling in your discomfort? Being able to do so better positions you to face and persevere through risk.  And, lastly, ask yourself if you can rely on your ability to problem solve, or figure it out. If a worst-case scenario became reality, would you have confidence that you could navigate your way through it? These are three effective ways to help you get clear on your risk-taking readiness.