Leadership is not a popularity contest. At some point, every leader faces the moment when doing what’s right for the organization conflicts with doing what people want to hear.

That moment tests courage. It tests conviction, but it also defines whether a leader leads for approval or for impact.

Unpopular decisions can range from restructuring teams, cutting budgets, ending long-standing projects or shifting company direction. These choices carry weight. They create discomfort. They often spark resistance. Yet without them, progress stalls and organizations stagnate.

A great leader undergoes these moments with clarity and confidence.

Related: Why The Most Effective Leaders Don’t Yell the Loudest — They Conduct

The cost of popularity in leadership

The desire to be liked is deeply human. Leaders are no exception. But prioritizing popularity over purpose carries real costs.

When leaders prioritize approval above all else, their decisions become diluted. Instead of pursuing the best path forward, they chase consensus at any cost. This leads to:

• Indecision: Constantly delaying choices out of fear of backlash.
• Short-term appeasement. Choosing what pleases today instead of what sustains tomorrow.
• Loss of trust. Teams eventually recognize when leaders avoid tough calls. Respect erodes even if “liking” remains.

It’s tempting to equate being liked with being trusted, but they are not the same. Trust is earned through consistency and integrity. Popularity can shift with the mood of the moment.

The myth of popularity in leadership

True leadership requires prioritizing the bigger picture. That may mean making a decision that frustrates or disappoints some in the short term but strengthens the organization in the long term. People want to be leaders because, at a conscious or unconscious, level, they want to be liked and popular amongst their peers. But this is very rare, especially for the great leaders.

Instead, leaders should value respect over approval. Respect is not about always agreeing. It’s about recognizing a leader’s fairness, consistency and willingness to act with integrity.

As Zev Gilboa states: “There’s a difference between popularity and respect. Popularity is doing what people want, and respect is doing what people need.”

For example, a leader who restructures a department may face criticism initially. But if that decision helps the company survive and thrive, respect grows. Over time, people often come to appreciate the difficult choices, even if they didn’t like them at the moment.

Related: The 3-Step Framework to Lead with Clarity and Confidence

How to navigate unpopularity: Practical steps

Making a tough decision is one part of leadership. Navigating the aftermath is another. Here are some practical ways leaders can handle these moments:

1. Be clear on the “why”

People can accept hard news if they understand the reasoning behind it. Leaders must clearly explain the purpose of the decision, the factors considered and the bigger picture it serves.

2. Communicate early and honestly

Silence breeds rumors. Leaders should not wait until the last moment to reveal decisions. Early, transparent communication minimizes speculation and builds trust, even in the most challenging circumstances. According to Newswise coverage of the study “New Study Examines How Leaders Explain Unpopular Decisions”, they found the following: “Research has consistently shown that explanations can help reduce the criticism and moral outrage managers face when they make unpopular decisions.”

3. Acknowledge the impact

Unpopular decisions often carry real consequences for individuals and teams. When a leader takes the time to acknowledge this reality instead of brushing it aside, it demonstrates empathy. By recognizing the human impact, resistance softens and space for understanding begins to open.

4. Stay consistent

Clarity is the foundation of trust. Mixed messages erode credibility, and once a decision is made, leaders must stand by it with steady conviction. Shifting direction under pressure not only signals weakness but also fuels uncertainty across the team.

5. Create space for dialogue

Allowing people to express frustration or ask questions does not reverse the choice, but it validates their experience and maintains respect.

6. Model confidence without arrogance

Confidence reassures teams that the leader believes in the path forward. Arrogance, on the other hand, dismisses concerns and silences feedback, eroding trust. The true balance lies in confidence that is anchored in empathy, where conviction and compassion move together. These steps do not make unpopular decisions “popular.” But they help teams process them constructively and preserve the trust needed to move forward together.

The strength found in tough decisions

Unpopular decisions often define a leader’s legacy. Rarely do teams remember the easy calls, but they do remember the hard ones.

When leaders prioritize the bigger picture over short-term approval, they demonstrate courage. They show that leadership is all about taking responsibility.

Over time, the hardest decisions often earn the deepest respect. Teams notice when a leader values integrity over applause. They see when choices are made to protect the long-term health of the organization, even if it comes at a personal cost.

Related: This Is the Leadership Superpower of 2025 — Do You Have What It Takes?

Conclusion

The ultimate measure of leadership is not how many people like the leader at any given moment. It’s how effectively the leader guides the organization toward its mission.

Popularity may feel rewarding in the short term, but respect lasts longer.

Leaders must remember: Making tough calls is not a failure of leadership. It is the very essence of it. The courage to prioritize the greater good, communicate with honesty and navigate resistance with empathy is what separates strong leaders from weak ones.

At the end of the day, teams don’t need leaders who always say what they want to hear. They need leaders who do what needs to be done.

Approval fades. Respect endures. And it is respect that allows leaders to leave a lasting impact.

Leadership is not a popularity contest. At some point, every leader faces the moment when doing what’s right for the organization conflicts with doing what people want to hear.

That moment tests courage. It tests conviction, but it also defines whether a leader leads for approval or for impact.

Franchising has always been a pathway for people seeking a proven business model, an established brand and a long-term financial opportunity. However, in recent years, we’ve seen a dramatic shift in who is seizing this opportunity. More young entrepreneurs — particularly Gen Z and younger millennials — are pursuing franchise ownership earlier in their careers compared to generations before them. What was once considered a late-stage career move has become a launchpad for ambitious young business owners.

I’ve seen firsthand just how quickly younger owners are entering and excelling in this industry, with their motivations, skillsets and expectations reshaping franchising. Every brand needs to be ready for this shift in ownership as younger franchisees are seeking entrepreneurial endeavors. In fact, in a 2020 survey by WP Engine and the Center for Generational Kinetics, nearly two-thirds of Gen Z (62%) said they have started or want to start their own business.

Here’s what’s driving the surge of youth in franchising and what franchise brands and young entrepreneurs should both know.

Related: Gen Z Is Quitting Corporate for a Different Kind of Business Opportunity: ‘The W-2 World Doesn’t Hold the Same Allure’

Why younger entrepreneurs are choosing franchising

A safer on-ramp to business ownership

Starting a business from scratch can be overwhelming, especially for someone in their 20s or early 30s. Younger entrepreneurs are increasingly drawn to franchising because it provides a structured, lower-risk pathway into business ownership through pre-established systems — like marketing, operational frameworks, training and support — already built into the model.

For those without decades of industry experience, franchising offers a roadmap by eliminating guesswork, shortening the learning curve and giving younger owners the confidence that they aren’t navigating their journey alone.

A desire for flexibility and autonomy

Younger generations have redefined what they want from their work lives. Flexibility and autonomy matter more than ever. Many want to build something of their own, but not at the expense of their lifestyle goals.

Franchising offers a unique balance: the stability and backing of an established brand, combined with the freedom to own and operate a business on their terms. In service-based industries like commercial cleaning, franchise owners can control their schedules, scale at their own pace and manage teams with a high degree of independence.

Better access to capital

Historically, funding was a major barrier for younger entrepreneurs, but today, that challenge is minimized. Small-business loans, SBA programs and franchise-friendly financing options are making it easier for first-time business owners to access capital.

As financing becomes more accessible, we’re seeing more franchise candidates in their 20s and 30s making the leap — especially in lower-cost franchise systems where the initial investment is more within reach.

Digital natives are built for today’s franchise landscape

Nowadays, technology touches every part of the franchising experience, from marketing, scheduling, staffing and operations, to communication, customer experience and more. Younger entrepreneurs, having grown up with much of this technology, are uniquely equipped to thrive in this environment.

Tech as a competitive advantage

Younger franchise owners tend to embrace operational software, automation tools, CRM platforms and digital marketing at a pace that often outperforms more traditional owners. Their experience and familiarity with technology encourage them to leverage data and trends to improve efficiency and customer satisfaction.

At Image One USA, we’ve seen younger franchisees quickly adopt our technology systems — from inspection platforms to real-time customer communication apps — with enthusiasm. Their comfort with digital tools helps them hit the ground running.

Purpose and community matter more than ever

For many young entrepreneurs, owning a business isn’t just about income; it’s about alignment with values.

Younger business owners want to feel connected to what they do. They care about sustainability, ethical practices and meaningful impact. Those franchises that demonstrate strong values and community involvement will have a major advantage in attracting young talent.

Built-in mentorship and support

Younger entrepreneurs actively seek mentorship and hands-on guidance. Franchising provides a built-in support network, from training and operations to peer groups and ongoing coaching.

A collaborative support model can resonate strongly with younger owners who are looking for transparency, open communication and strong leadership from their franchisor — and they perform better because of it.

Related: Think You’re Too Young to Own a Franchise? Think Again.

What this shift means for franchise brands

The growing youth movement in franchising is exciting, but it also requires franchisors to evolve. Younger entrepreneurs learn differently, expecting digital resources, multimedia modules and clear, accessible documentation. Franchise systems that still rely solely on in-person instruction or paper manuals risk alienating this demographic.

Technology must also be seamless, as brands with outdated operational systems will be immediately noticed by younger candidates. Franchisors should prioritize regular audits of their tech stack to ensure that communication, data management and operational tools are intuitive and efficient for those who will use them.

Equally important is communication. Younger owners value transparency and authenticity, and they expect real-time access to information. Brands that use digital message boards, shared workspaces and franchisee portals to maintain open lines of communication will earn their trust.

Finally, franchisors must recognize that clear growth paths matter. Many young franchisees are thinking well beyond single-unit ownership, looking for opportunities to scale, take on leadership roles and build long-term business portfolios. Brands that highlight and support these pathways will easily stand out in a competitive market.

Related: Franchising: The Younger Generation Steps Up

The future of franchising is being built by young people

Younger entrepreneurs are bringing innovation, passion and a fresh approach to franchising. Their comfort with technology, desire for meaningful work and willingness to embrace structured business models make them a powerful force shaping the future of the industry.

For franchisors, this generational shift is an opportunity — not a challenge. Brands that modernize their systems, invest in support and align with the values of younger owners will thrive.

As someone who has spent decades in franchising, I’m more encouraged than ever by the next generation. They’re committed, capable and ready to lead. The surge of youth in franchising isn’t just a trend; it’s the beginning of a new era of entrepreneurship.

Franchising has always been a pathway for people seeking a proven business model, an established brand and a long-term financial opportunity. However, in recent years, we’ve seen a dramatic shift in who is seizing this opportunity. More young entrepreneurs — particularly Gen Z and younger millennials — are pursuing franchise ownership earlier in their careers compared to generations before them. What was once considered a late-stage career move has become a launchpad for ambitious young business owners.

I’ve seen firsthand just how quickly younger owners are entering and excelling in this industry, with their motivations, skillsets and expectations reshaping franchising. Every brand needs to be ready for this shift in ownership as younger franchisees are seeking entrepreneurial endeavors. In fact, in a 2020 survey by WP Engine and the Center for Generational Kinetics, nearly two-thirds of Gen Z (62%) said they have started or want to start their own business.

People keep telling me “DEI is over,” as if a headline has more power than the people inside the business. From where I sit — as a woman, a psychologist and an executive coach — DEI isn’t dying; it’s finally growing up. The checkbox version is what’s collapsing.

This shift is driven by a younger, more diverse generation that would rather walk away than stay in cultures that only tolerate them; by customers and investors who pay attention to how you, as a leader, treat people, not just what you sell; and by global competition, where the companies that innovate fastest are the ones that actually use the full range of their talent.

In that setting, glossy statements, one-off trainings, and heritage month campaigns with nothing underneath them are just another “strategy.”

Related: What Every Entrepreneur Can Learn from NCAA Coach Dawn Staley’s Leadership Style

The end of performative DEI

For years, companies treated DEI like an events calendar. A training here, a panel there, a statement when the news got loud. That old playbook relied on optics and urgency, not necessarily on outcomes, and it is the part that is fading. Today, employees expect transparency. Customers and employees compare what you “promote” online with what they actually experience. Under that level of scrutiny, performative moves fall apart.

These days, many organizations start to adapt and tie DEI directly to talent, innovation and customer experience. They tackle more complex conversations about who gets hired, who gets promoted, who receives stretch work and whose voice shapes key decisions.

They are shifting from one-off workshops to capacity building through coaching and accountability, so inclusion naturally becomes a leadership muscle for them, not another marketing message.

Dismantling DEI myths

A lot of DEI fatigue comes from old misconceptions. Some say DEI is only about race and gender. Well, yes, those are essential, but inclusion goes wider. It means building a culture where neurodivergent employees, people with disabilities, caregivers, veterans and everyone on your team can say, “I matter here.”

Another myth says DEI just divides people. Unspoken inequity, broken communication and the absence of trust are what actually divide people. When done strategically, DEI gives people the correct language for what they are already feeling and a specific, workable framework to address it.

I also get something like, “We don’t have time for DEI because we’re focused on performance.” That’s a false choice. Performance and inclusion are cause and effect. When people feel seen, respected and safe to challenge ideas, they make the work better. I’ve watched teams move from groupthink to genuinely creative solutions once psychological safety was in place.

That is the deeper shift. DEI is no longer about managing optics through flawless, unrealistic marketing messaging. It’s now building a more human-centered style of leadership that gets you better thinking, better products and better retention all at the same time.

How today’s top executives show up differently

The strongest leaders I coach are not asking what DEI program they should launch next. They think about how they need to lead differently.

They start with a simple pattern check. They look at the last month and ask who receives their time, trust and opportunities and who never appears on that list. That one question exposes bias faster than any dashboard ever could.

Then they change how they run rooms and make decisions. They identify whose voices they have not yet heard and protect the people who raise uncomfortable talking points. They treat opportunity as a system by insisting on diverse slates for roles and pairing stretch assignments with real support. Most importantly, they make inclusive behavior part of what “good leadership” means in their organization, embedded into expectations, feedback and promotions so respect and voice become non-negotiable.

Related: 3 Workplace Biases Inclusive Leaders Can Reduce Right Now

What progressive leadership looks like at work

When DEI becomes a leadership strategy instead of a side project, people will feel it and you, as a leader, can measure it. You’ll see engagement rise, especially for people who were once on the margins. You’ll see turnover drops in roles that used to be revolving doors.

At my company, we teach a model that one client chose to integrate into how they led their business. They held listening sessions across levels so people could speak honestly about their experiences. They invested in executive coaching, then opened coaching access more widely, so development felt more equitable. Within a year, employees reported feeling safer to speak up, engagement scores climbed and more diverse candidates moved into leadership roles because barriers were finally removed.

That is belonging in action. Once that trust is in place, teams stop playing it safe. People challenge ideas, offer new perspectives, and push for better solutions.

How to fix systems instead of people

If I could redefine DEI for the next decade, I would anchor it in three words. Belonging. Equity. Leadership.

Belonging is the lived experience; the test of whether your people can confidently speak without rehearsing something like, “I feel safe, respected and valued for who I am at work.”

Equity lives inside systems, in how you hire, promote, evaluate, pay and share opportunity, and it moves you from fixing people to fixing processes.

Leadership is the lever that makes both belonging and equity real. Inclusive leadership must be a core competency, as fundamental as budgeting or strategy, with every leader trained, coached and held accountable for how they use their power.

So when my C-Suite clients tell me they feel pressured to pause DEI because of criticism or budget cuts, I only ask one question: When the headlines change, what do you want your people to say about working for you? Leaders who know their values don’t walk away from the very work that builds trust. They may refocus or refine DEI, but they will never abandon it.

So yes, DEI is not disappearing. It’s not dying. It’s only evolving into the way progressive organizations will be led. When workplace leaders stay in this course, they will have what others can’t buy later: a culture built on trust, and a business strong enough to compete for both talent and markets over the long term.

People keep telling me “DEI is over,” as if a headline has more power than the people inside the business. From where I sit — as a woman, a psychologist and an executive coach — DEI isn’t dying; it’s finally growing up. The checkbox version is what’s collapsing.

This shift is driven by a younger, more diverse generation that would rather walk away than stay in cultures that only tolerate them; by customers and investors who pay attention to how you, as a leader, treat people, not just what you sell; and by global competition, where the companies that innovate fastest are the ones that actually use the full range of their talent.

If you’ve ever owned a pet, you know they’re different from animals that live in the wild. Out there, competition is fierce because every day is life or death. But at home, everyone has to play nice and get along.

Running a business in a niche market is a bit like being an indoor cat. There’s still competition, but if you’re too aggressive towards the other players in your space, it makes the space uncomfortable for everyone.

Conversely, when everyone in a narrow category gets along and does well, the whole category benefits. Think of it this way: Guests want to visit the house where the cats compete by doing tricks for treats, not the house where fur is always flying.

That’s why I’ve always welcomed healthy competition in the roof restoration industry, which my company Roof Maxx disrupted by offering a cost-effective and eco-friendly treatment for asphalt shingles. There’s no point in being threatened by others, as long as we’re all behaving ethically and responsibly in our shared space.

Below, I’ll tell you more about what I think that means — along with how it benefits all parties and how to recognize when competition isn’t friendly anymore so that you can take proper steps to protect yourself.

Related: I’m Extremely Competitive — Here’s How I Keep It from Becoming a Problem in my Business

Why a rising tide raises all boats — especially in smaller ponds

Let’s put aside the pet metaphor and talk about a concrete example from my career. Most homeowners I talk to aren’t even aware that roof restoration is an option for them. That’s how small the category is, especially when you’re serving the residential market.

Roof Maxx has grown into a national brand. Our dealers collectively generate more than $200 million per year in total revenue through roof repairs, maintenance, cleaning, restoration and replacements. Our dealer network represents a different kind of roofer: One focused on helping property owners avoid costly roof replacements by giving them real options. In fact, roughly 80% of roofs being replaced nationwide could be saved, often extending their life by a decade or more.

But our goal isn’t just to stay in business. It’s to make roof restoration an option for every homeowner with treatable shingles. Not only will that help a far greater number of people save money on protecting their homes, but it will also build an industry worth roughly $10 billion each year.

The key to doing that is educating people. And that will go much faster if others are spreading awareness about residential roof restoration than if we have to do it all by ourselves.

I know this because I’ve already watched it happen quickly in the commercial industry. All the restoration products that currently exist for commercial roofs have sprung up over the last 40 years or so. The inspection, restoration and maintenance programs that ultimately cropped up around them are even younger.

So the more companies that are out there doing residential roof restoration correctly, the more demand there will be for what we do. I don’t mind someone trying to be the Pepsi to our Coke.

Related: 3 Reasons Why I Gladly Welcome Competition

Why you have to choose your battles more carefully in close quarters

Not all competitors have the same idea of what constitutes friendly competition. But often, I find it’s better to be lenient about minor transgressions than it is to bring out the big guns.

I’ve seen other businesses use our graphics, or conspicuously similar ones, without obtaining our permission. I’ve seen marketing copy that uses word-for-word claims we’ve made. But I’m not a particularly litigious guy, and most of the time, these things don’t bother me too much. In fact, they can even be helpful sometimes.

Roof Maxx is the most established brand doing what we do. So if someone is parroting our claims or borrowing aspects of our branding, they’re practically giving us free advertising. Most customers are going to do at least a little research before they commit to treating their shingles, and when they do, they’ll probably find out that we’re the bona fide original with the most research backing up our product. I have a pretty high opinion of most people, and I trust them to read the writing on the wall at that point.

As leaders in the space, the way we respond to issues like this also helps set the tone for others. I don’t want an antagonistic relationship with the other businesses in my space. I prefer the competition to be friendly, and I understand how much better it is for the industry as a whole.

Related: The 4-Step Strategy That Helped Us Create a Fast-Growing New Niche in a Legacy Industry

Teaching others how to treat you goes both ways

But sometimes, a competitor behaves in ways that give the whole industry a bad name. Years ago, another roofing business targeted our dealers and fed them misinformation about our product in an attempt to make them quit.

What they did wasn’t just potentially harmful to our business. It was harmful to the entire concept of roof restoration as a viable solution for residential properties because it interfered with customers’ ability to make properly informed decisions.

It was also illegal. That’s what’s known as tortious interference, which is when a third party knowingly and wrongfully disrupts an established contractual agreement. So we sued, and the court found them guilty — not only of deceptive trade practices, but also of intentionally destroying evidence.

The moral of the story is that when you’re all in the same small community, friendly competition is good for everyone, and treating each other with compassion is the best way to keep things friendly. But keeping your community safe means protecting it with strong boundaries. And a boundary is only as good as your willingness to enforce it.

Be friendly. Be kind. And if others mistake your kindness for weakness, don’t be afraid to prove them wrong. That’s how you earn goodwill in your category without sacrificing respect. And it’s how you set an example that your competitors will want to follow, so that all of you deliver a more professional experience to customers.

If you’ve ever owned a pet, you know they’re different from animals that live in the wild. Out there, competition is fierce because every day is life or death. But at home, everyone has to play nice and get along.

Running a business in a niche market is a bit like being an indoor cat. There’s still competition, but if you’re too aggressive towards the other players in your space, it makes the space uncomfortable for everyone.

The toughest part about entrepreneurial leadership isn’t the strategy, hiring and team building, or the uncertainty of market cycles. It’s the mental load you carry when you’re developing something new and unproven.

Nobody prepares you for the emotional tolls of entrepreneurship — the strain of making judgments based on insufficient information, the obligation of being a stabilizing force for your team or the fact that every decision you make today influences whether the company will continue to exist tomorrow. Those pressures take a psychological toll, and it’s why many leaders quietly hit a wall even before the outside world sees any cracks.

Most founders and executives think that mental health is something they can just “get to later,” once the business grows or the chaos eases up. But the truth is, the chaos never really ends. What changes is your capacity to carry it. And that capacity depends largely on your mental health. It shapes judgment, instinct, every coaching moment and how you handle the conflicts you navigate. This also negatively impacts risk perception, problem-solving, adaptability and even how safe your team feels in your presence.

When leaders come to regard mental health as a performance factor, everything about their leadership style changes.

Related: Culture Isn’t Soft. It’s the System Running Your Company

The fine line between grit and dysfunction

Beyond stretching your skills, high-level leadership tests your ability to remain calm under pressure. When the stakes climb, your clarity of thinking as well as your capacity to stay grounded are also tested. There are times when everything seems fragile: the company, your confidence and your sense of control. In those situations, pressure does not create new problems, but rather exposes existing ones. If you add burnout or isolation to that stress, it will only exacerbate rather than relieve it.

Burnout is especially dangerous because it often gets viewed as dedication and a willingness to “grind.” But when burnout enters the picture, decisions start to feel harder than they should. Work that once energized you becomes draining. Success brings little relief, and setbacks feel unusually personal. These changes are easy to interpret as personal weakness or loss of edge, when they are often the body and mind reacting to sustained strain.

Many founders get used to a constant state of high stress, even a sense of dread and call it motivation. In reality, that tightness in your chest isn’t an acceptable side-effect of ambition. It’s a warning. Staying in that state for too long narrows your thinking and fogs your judgment.

Related: 3 Daily Habits That Will Positively Affect and Protect Your Mental Health

Stop side-stepping and start resetting

When leaders hit that point of being overwhelmed, the instinct is often to reach for easy workarounds or crutches to change their mental state and shut the day down. A second drink, a late-night binge meal or scrolling until the brain finally gives out can feel like reasonable ways to decompress. While these short fixes provide temporary relief, they drain your capacity the next morning by causing sleep disruption and disguising the real underlying problem. You wake up feeling unhappy and aware that you are not helping yourself at all, realizing that you cannot fix your problems or build resilience through band-aid solutions.

Real progress happens when you create gaps in the chaos to ground yourself and reflect. It could be a ten-minute walk to drop your heart rate, or sweating it out on a treadmill to burn off the adrenaline. It can also look like putting the phone away to truly enjoy dinner with family or spouse. These small activities help interrupt the feeling of “being on the hamster wheel” and effectively reset your mood and cognitive functioning.

Mental literacy can be a competitive advantage

One of the greatest barriers to mental health for leaders is the confidence that has made them successful to date. Leaders are wired to bet on themselves. They assume they should be able to outthink their anxiety or push through depression or other challenges through sheer force of will. Many won’t admit they’re struggling because they worry about shaking their people’s faith in their vision and dependability.

This silence pushes problems underground, where they grow in the dark. A key missing tool here is education and understanding. When leaders understand the mechanics of stress and how it impacts their cognitive functioning, they stop viewing their struggles as character flaws and start seeing them as operational challenges that can be solved.

Understanding mental health conditions and symptoms allows leaders to better identify what they are feeling. It provides the awareness to appreciate that they are not “losing their edge” but simply dealing with something that requires attention and proactivity to overcome.

Often this leads to seeking therapy or expert coaching that can be a great strategy not only for effectiveness as a leader, but also for happiness, relationship health and longevity.

Consistency is your most critical KPI

A leader’s mental state never stays private for long. You, as the leader, set the emotional tone for the organization. If you show up as emotional or on edge, the team feels the pressure immediately. They start walking on eggshells because they are wary of triggering the wrong version of you. When the team is uneasy or potentially even scared, they stop sharing bad news. They hide mistakes. Innovation and creativity die because nobody wants to risk the friction and people “go heads-down”.

Alternatively, when leaders manage their mental health with intention, they show up with emotional steadiness and authenticity. That consistency tells people it is safe to ask questions, admit mistakes and take risks. It allows you as a leader to give the company what it needs most in uncertain conditions: a leader capable of sound, sustained judgment.

Ultimately, the most valuable component of your company’s balance sheet is the strength and dependability of the people in leadership positions, including you as the ultimate person in charge. If you protect that asset, you give the business the best chance to weather the tough challenges and setbacks, and to guide the company to success with a clear mind and with your feet firmly planted on solid ground.

The toughest part about entrepreneurial leadership isn’t the strategy, hiring and team building, or the uncertainty of market cycles. It’s the mental load you carry when you’re developing something new and unproven.

Nobody prepares you for the emotional tolls of entrepreneurship — the strain of making judgments based on insufficient information, the obligation of being a stabilizing force for your team or the fact that every decision you make today influences whether the company will continue to exist tomorrow. Those pressures take a psychological toll, and it’s why many leaders quietly hit a wall even before the outside world sees any cracks.

“It never hurts to ask.”

People nod when they hear that. They agree. Then they ignore it.

Because asking feels risky. Asking puts your ego on the table. Asking opens the door to rejection. Asking forces you to admit you want something.

Most adults hate that feeling.

So they stay quiet.

They convince themselves that the timing is off. The ask is too big. The other person is too busy. The answer is probably no anyway. That logic sounds responsible. But, it is actually expensive.

Related: How Crisis Taught Me to Ask for Help

The opportunities that die quietly

The most common answer you will ever receive is not ‘no.’

It is silence.

Not because the other person would have said no, but because you never asked in the first place.

I see this constantly. People want the deal, but never send the email. They want the raise, but never start the conversation. They want the partnership, but wait for the perfect intro. They want the house, but never make the offer.

They assume rejection will hurt more than regret. They are wrong. Regret compounds. You remember the chances you did not take far longer than the nos you received and moved past.

Why asking feels hard as an adult

Kids ask for everything. Can I have dessert? Can I stay up later? Can I try again?

Adults lose that instinct.

Somewhere along the way, asking got wrapped up in pride. We started believing self-reliance meant silence. We confused confidence with not needing anything from anyone.

That mindset kills momentum. Entrepreneurship does not work without asking. Neither does leadership. Neither does growth. Every meaningful step forward involves a request.

Capital.
Advice.
Forgiveness.
Help.
A chance.

No one builds anything alone, even if they pretend they did.

Real estate taught me to ask before anything else

My entire career started because I asked questions. I did not grow up knowing how to invest. I did not wake up one day magically understanding deals, capital stacks or risk tolerance.

I asked.

I asked investors how they thought about money. I asked developers why certain projects worked and others failed. I asked smarter people to explain things I did not understand yet.

If I had stayed quiet, I would still be selling one deal at a time and wondering what else was possible. Instead, curiosity changed the trajectory. Those early questions led me from brokerage into investing. They led me into rooms I did not think I belonged in yet. They eventually led to investing in more than 150 deals.

That shift did not happen because I was fearless.

It happened because I was willing to sound curious. Every career change I am proud of started with a question.

Related: Asking for Help Might Be the Key to Your Success

Asking is the skill behind every deal

Real estate is one long exercise in asking. You ask sellers for flexibility. You ask buyers to stretch. You ask lenders to move faster. You ask partners to trust your vision.

Some say no.

Many say yes.

The wins never come from the asks you did not make. Some of my best deals came from questions that felt uncomfortable in the moment. Offers that felt aggressive. Conversations I almost talked myself out of.

Almost. That word matters. Almost asking does nothing. Every meaningful transaction I can point to today traces back to a moment where I chose discomfort over silence.

Coffee, lunch and the power of curiosity

I once wrote about how I try to meet someone new for coffee or lunch almost every day. People asked me what the secret was. There is no secret. I ask questions.

Those meetings are not about pitching. They are not about proving how much I know. They are about listening and learning.

What are you working on?
What problem keeps showing up?
What would you do differently if you started today?

Those questions unlock opportunities you cannot Google.

Some meetings turn into friendships. Some turn into investments. Some turn into nothing at all. All of them compound perspective. Curiosity turns conversations into catalysts.

Related: How to Ask for the Help You Need To Succeed

Rejection is data, not a verdict

Here’s the mindset shift that changed everything for me. No is not personal. It is informational. No tells you timing is off. Or priorities differ. Or the structure needs work. No sharpens the next ask.

People who avoid asking treat rejection like a character flaw. People who win treat it like feedback. There is a massive difference.

The most successful people I know hear no all the time. They just do not stop because of it. They keep asking better questions.

They keep adjusting the approach. They keep moving.

Asking builds confidence faster than winning

This sounds backward, but it is true. Confidence does not come from success. It comes from repetition.

The more you ask, the less scary it becomes. You learn how to phrase things clearly. You learn how to read the room. You learn that most people are reasonable and many are generous.

You also learn that a no does not break you. Avoiding the ask keeps fear alive. Making the ask shrinks it.

Action beats anxiety every time.

Leaders who ask create stronger teams

Leaders who never ask for input think they look strong. They do not. They look closed off.

Great leaders ask questions constantly. They ask for ideas. They ask for feedback. They ask for help when they need it. That behavior creates trust. Your team does not expect perfection. They expect honesty and direction.

Asking invites ownership. Silence creates distance. If there is something you want, ask.

Ask clearly. Ask respectfully. Ask without apology.

Careers change because of questions. Relationships deepen because of questions. Opportunities appear because someone spoke up.

“It never hurts to ask.”

People nod when they hear that. They agree. Then they ignore it.

“I’ll launch when the timing is better.”

“It’s just not the right economy for something new.”

“What if no one’s spending money right now?”

If you’ve ever thought this — or heard it from others — you’re not alone. In times of economic uncertainty, hesitation feels logical. It’s wise to be cautious, and besides, you want to give your startup the best possible chance of success. Waiting just makes sense.

Except that all of that is — excuse my language — total hooey.

If you’re building something people truly need, the timing doesn’t have to be perfect. Great startups don’t take off because the economy is booming — they take off because they solve real problems. And yes, that can happen even in a downturn. Here’s why.

Related: Market Volatility Isn’t Your Enemy — It’s Your Greatest Opportunity. Here Are 6 Proven Ways to Profit From the Chaos.

When being small is a plus

I get it — launching in a time of economic turmoil seems like an obviously bad idea. But here’s the thing: When founders say they’re holding off because “no one’s spending right now,” they’re thinking like established companies, not startups.

The reality is that in the earliest stages, you’re not trying to win over the whole market. You’re just trying to find a few people — your first 10, 50, maybe 100 users — who have a specific, urgent problem and are actively looking for a solution.

In that context, macroeconomic trends don’t matter nearly as much as you might think. Recessions don’t eliminate pain points. In fact, they often magnify them. If your product solves something real, there will always be someone willing to pay for it. Plenty of now-household names started during downturns: Airbnb during the 2008 crash, Uber in 2009 and WhatsApp the same year. These companies didn’t succeed despite the recession — they succeeded because they solved pressing problems, and the downturn made people more open to new, cost-effective solutions.

Unless you’re selling something extremely niche to an industry in freefall, the ups and downs of the economy won’t make or break your startup. Your footprint is too small for the broader market to meaningfully affect you — and that’s a good thing.

Most startup struggles are internal, not external

I’m going to lay out an uncomfortable truth: If your startup fails in a downturn, odds are the economy wasn’t the real problem. More often, the root cause is internal — a lack of product–market fit, poor execution, burning resources on the wrong priorities or giving up too early.

The data backs this up, with research showing that products launched during recessions outperform on several measures. A 2023 study found that consumer products launched during a recession survive 14% longer on average than comparable products launched during more prosperous times. This is for a few reasons: the marketplace is less cluttered, making it easier to get noticed. Advertising is often cheaper. Also, releasing a product in a recession creates the impression of corporate health, boosting customer confidence.

“I thought discretionary-product launches would be more likely to fail, because nonessential purchases tend to decline in tough economies,” M. Berk Talay, the lead author of the study, told Harvard Business Review. “But the effects are consistent across products and categories. A recession might be the ideal time to launch your product no matter what it is.”

The bottom line? Perfect conditions don’t exist. The real risk isn’t launching in a bad economy; it’s letting fear stall your momentum while someone else solves the problem you sought to tackle.

Related: Why Adaptive Leadership Is the Key to Success During Market Volatility and Times of Uncertainty

How to launch in any economy

Once you accept that the economy isn’t an adequate reason to wait, the next step is figuring out how to move forward anyway. The good news that while the economic backdrop may be different, the fundamentals of launching a startup are the same.

The first step is to get clear on who your product appeals to, and really understand their needs. In a downturn, that often means focusing on customers who have an urgent problem — one that’s painful enough that they’re actively seeking a solution. Zoom is a great example: while it wasn’t launched during the pandemic, its laser focus on making virtual meetings seamless met an urgent, non-negotiable need when in-person work shut down. If your product can save people time, cut costs or remove a major headache, it has a fighting chance no matter the market conditions.

From there, resist the urge to go big out of the gate. Start small with a minimum viable product (MVP) that delivers immediate value, and test it with a small group of early adopters. Their feedback will not only shape the product, it will also help refine how and where you market it to reach similar customers. Lean times demand discipline, so be ruthless about where you spend your time and money. Focus on the activities that reliably bring in users and skip the ones that “might” pay off months from now.

As a bootstrapped founder, this is advice I would (and have) given to anyone starting out in any market: understand the value you’re bringing, build lean and listen to your customers. The economy will rise and fall regardless of what you do, but the habits you develop in a downturn — discipline, focus and adaptability — will serve you long after conditions improve. If you can prove your idea works when times are tough, you’ll be ready to scale when the tide inevitably turns.

“I’ll launch when the timing is better.”

“It’s just not the right economy for something new.”