Stuck Making a Big Decision? Say ‘Maybe’ More.

Maybe gets a bad rap. It’s a word relegated to the land of indecision and wishy-washiness; it conjures up images of hedging politicians who avoid taking a courageous stance and of parents attempting to appease incessantly nagging toddlers: “Maybe you can have that lollipop later” (just please be quiet).

But here’s what I know to be true: incorporating ‘maybe’ into my decision-making process has given me and my coaching clients abundant freedom to live and lead in the way we most aspire.

Here’s how.

As humans, we’re wired to do two (of many) things. We’re wired to 1) self-protect in service of our survival (“That saber-toothed tiger is coming at me, I need to fight or flee!”) and 2) categorize people and situations into existing mental models so we can feel a sense of control over our dynamic, complicated, and contradictory world (“I’ve seen a saber-toothed tiger attack a friend, I now know these tigers are bad, I should always run or hide from them.”).

This wiring plays out in how we make decisions. It means we frequently engage in ‘worst-case scenario’ thinking to ensure we’re one step ahead of that lurking, dangerous trap. We imagine a difficult conversation with our boss resulting in a termination. We see that taking on a challenging new project and potentially failing will reveal our utter inadequacy. Far safer, then, to keep quiet and lay low: saber-toothed tiger avoided.

It also means we readily trust that past experiences, ones that have been catalogued in our memory, will play out in the exact same way in the future. We believe we’re all-knowing. We’re convinced that Sheila will always blowup at us, no matter how delicately we ask for help. We know that team meetings won’t ever improve because previous input we’ve offered wasn’t incorporated. We accept the status quo because we know these saber-toothed tigers don’t change their ways.

This tendency to prepare for the worst and trust that we know exactly how a decision will play out is a bit foolish. We’re rarely really under imminent threat and we’re not prescient beings. And, this fear-driven orientation limits our growth and ability to develop into better versions of ourselves. The best way to release from this constraining instinct is to train our minds that maybe an alternative is true so we can see the spectrum of our choices more vividly.

Me: “It Doesn’t Seem Wise”

Let’s apply this all on me for a minute. For years I wanted to launch my own leadership coaching business and I talked regularly with friends and family about it. My personal values around independence, creativity, and curiosity drove me, in addition to feeling stagnant and isolated in my role as internal executive coach at a national non-profit. When articulating my deeply held desire, though, I always got hijacked by my brain’s natural wiring. I’d think, “It just doesn’t seem financially wise. I’ve got a stable gig with good benefits. What if I make no money operating independently?” Or it sounded like, “I know I crave predictability and a plan, the fluctuating business model of a consultant is counter to my temperament.” Fear and bad prescient thinking kept me firmly rooted in an unfulfilling current state.

Then, a friend, exasperated with my regular ruminations of wanting to go out on my own, went off on me a bit. “Maybe you will make no money and you’ll be miserable!” she exalted. “Or, maybe you’ll double your income. Maybe you’ll discover you get energy from the more extreme highs and lows. Maybe you’ll sign a book deal and get an influx of new, unexpected opportunities. Maybe you’ll decide in a year to abandon it all for simple living in rural Oregon. Who knows?”

“Oh,” I thought, a bit jolted and disoriented. “I guess maybe those alternatives could be true.”

Giving voice to maybe, in all its forms, unhooked me from my natural wiring and gave me freedom to believe in different possibilities and take action that I longed for.

And, I see that exploring alternative maybes emboldens my clients all the time.

Sandra: “I Just Need to Suck it Up”

Sandra is a client who works at a tech startup and recently received feedback from her male boss that she should, ‘smile more’ because she comes off as a bit cold to colleagues. According to him, it makes people less inclined to offer her feedback, collaborate with her, and solicit her advice. She was composed as she recounted the conversation recently to me but enraged beneath the surface. “I can’t help but think he wouldn’t give this feedback to a male counterpart,” she explained, “But he’s my boss and controls my ability to advance here, so I need to just suck it up and put on a happy face.”

Sandra felt stuck. She’s a strong woman with a desire to exercise her most honest self, but fear of a devastating outcome and past experiences in a totally different environment (read: US Naval) triggered reminders to respect authority at all cost.

Enter: maybe.

“Maybe you do just need to suck it up,” I offered. “Maybe the worst-case scenario is true: he’s a sexist pig who is out to sabotage your career if you don’t step in line.”

“Or, maybe he’s completely clueless about his blind spots because no one’s been brave enough to name them; he could be mortified and apologetic to know his impact on you. Maybe there’s a nugget of truth in the feedback that’s worth mining for and having you act on with agency. Maybe this is evidence you should quit and seek out a corporate culture that’s aligned with your values. What happens when you step into this alternative reality of ‘maybe I don’t need to just suck it up’?” I asked. “What do you want to do?”

Sandra, a bit jolted and disoriented, began to consider alternative actions that weren’t guided by fear or prescience. She shared:

“Maybe I could honestly share how his feedback landed with me — how it made me feel like I need to take on a cheerleader personality if I want to succeed here — and to better understand what he intended and what learning there might be for both of us out of this. Perhaps it would even garner his respect for me, not retribution. Or, maybe I could gather more data on feedback he’s given to male counterparts. That could let me better know whether this really is insidious sexism and what action I’d want to take from there.”

By entertaining the possibility that ‘maybe’ she could react in a different way than her instinctive wiring dictated, Sandra saw other ways to engage with the feedback that felt responsible and empowering

Paul: “I Could Never Make it Happen”

Or, let’s look at my client, Paul.

Paul is the primary breadwinner in his family with a wife and three kids. He works at an established, high performing company with amazing benefits. As a result, he feels a real, rational resistance to embracing financial risk. But, at this mid-career juncture he’s reconciling his current reality with future hopes and notices a longing to pursue a career with greater social impact. Paul joined the Peace Corps decades ago out of college with noble aspirations to change the world. Those aspirations have been sidelined for a traditional corporate and suburban life. He admits he’d love to run a family foundation or lead a non-profit focused on global health, but laments that he could never make it happen given his predominantly corporate experience, current compensation demands, and the mental model of: “It’s just not what men my age do.”

Maybe that’s true. Maybe Paul needs to accept his professional choices and focus on maintaining financial security for his family. But it feels like that decision is rooted in fear of the unknown and biased data that he’s treating as complete truth. And, it feels wildly constraining.

My coaching of Paul requires that I help expand his ability to wonder about alternative maybes. I’ll probe him with considerations of:

  • Maybe the claim that your corporate experience is irrelevant and your compensation demands unreasonable is inaccurate. How might you test that?
  • Maybe plenty of men your age have made this exact career change. How might you find and learn from them?
  • Maybe your family could be even more ‘provided for’ if a salary cut accompanied a more professionally fulfilled and engaged father. How could that be true?
  • Maybe this is an opportunity for your wife to test the boundaries of her earning potential and discover a renewed sense of professional success. Might that be freeing to you both?

For Paul, maybe can free him up to see his dilemma from varied dimensions and take action in new ways towards the professional life he aspires.


The purpose of incorporating maybe more regularly into our decision making isn’t to locate the ‘truth’ or the ‘right answer’ in a difficult decision-making process. The point is to recognize that a number of potential ‘truths’ exist and we have the power to internalize the ones that give us the most freedom. We are rarely 100% assured of how a complicated decision will play out; there are often too many variables at play and constantly changing information. The point is to expand our range of possibilities and imagine that maybe the worst case won’t happen and maybe a familiar situation won’t play out in the way we predict. Maybe my income will double. Maybe Sandra’s boss will become an advocate for women in the workplace. Maybe Paul’s wife will feel forever grateful that his passion pursuit meant she discovered untapped professional ambition. Maybe none of these will be true. But, by choosing to explore, trust, and indulge in alternative maybes we are all choosing to live and lead in the way we aspire.