Why Every Leader Needs A Side Hustle Mindset
The line between entrepreneurship and traditional leadership is becoming increasingly blurred. A 2024 study by researchers at James Cook University found that both managers and entrepreneurs require similar core abilities—dynamic capabilities, which include self-efficacy, alliance management and marketing capabilities—to excel in post-COVID, VUCA work environments (volatile, uncertain, complex, ambiguous). Increasingly, professionals across sectors are embodying this shift. The percentage of people working both salaried and entrepreneurial jobs (i.e., side hustles) has grown from 13% in 2020 to 38% in 2025, down slightly from 44% in 2022, according to annual LendingTree surveys.
While many professionals pursue side hustles for the extra income, the benefits run far deeper. Side hustles require and foster a particular mindset—and build a skill set—that can add massive value to salaried roles and shore up long-term career security. That is because these high-value dynamic capabilities (a side hustle mindset) are exactly what companies need to stay competitive and relevant in times of rapid change, tech innovation and upheaval.
Why The Side Hustle Mindset Matters More Than Ever
With all the economic uncertainty and instability In this job market, the invitation to all professionals is to be more adaptive, scrappy and inventive. But leaders in particular must deepen their entrepreneurial agility. Delivering excellent results is necessary, but no longer sufficient.
As AI and lean teams shrink org charts, leaders must create their own value-add rooted in their distinctly human gifts and talents. For rising and established leaders alike, career longevity requires building more and more options for one's career trajectory—as opposed to clinging on to the dream of 'climbing the ladder' within the same organization.
We can meet this moment with the side hustle mindset, which encompasses skills like resourcefulness, self-direction, calculated risk-taking, market-driven thinking and digital fluency.
What The Side Hustle And Mindset Can Look Like At Different Career Stages
For early-career professionals, side hustles can serve as self-created, self-driven apprenticeships that solidify fundamental professional skills: communication, organization and time management, client or customer service, analytical thinking and problem-solving.
For those in extended job searches, side hustles can also provide structure, a sense of purpose, fulfillment and momentum. They also offer valuable work experience that can be parlayed into future salaried positions or scalable businesses.
In other words, a side hustle can be the fastest way to build portfolio experience and road-test your career interests—on your own terms.
For mid-career professionals and leaders, entrepreneurial throughlines in your professional branding can set you apart in a crowded and competitive job market. Review your body of work through an entrepreneurial lens and determine how to weave those elements into your career narrative and highlight them across your professional assets (LinkedIn profile, online bio, executive summary on your resume). It could be the differentiator that lands you the coveted leadership role you've been working towards.
If you have a side hustle, leverage it to grow your leadership, innovate solutions and develop your risk management skills—all while building your executive presence and honing your ability to pitch ideas with confidence.
A side hustle (or the mindset alone) will force you to expand your horizons and your network—all of which strengthens your 'career insurance' for when 'stable' jobs suddenly disappear.
For senior leaders, you likely already have a plethora of entrepreneurial leadership examples to draw from—conduct an audit on your own or with an expert to ensure you're positioning yourself strategically and advantageously.
At this stage of your career, side ventures, investment projects or advisory work can keep your entrepreneurial edge sharp. Research, vet and join appropriate peer cohorts or engage in micro-learning to stay relevant without overcommitting yourself given the demands already on your plate.
How To Cultivate A Side Hustle Mindset—Even If You're Not Launching A Business
No matter your career stage or specific circumstance, given how the landscape is trending, it is imperative to think like a founder in your role. Practice this by identifying root problems, creating actionable solutions and carefully studying the market. Invest in your entrepreneurial skill-building through small-scale experiments (entrepreneurial programs, pilot projects, advisory roles, partnerships) that let you fail fast and help you adapt even faster.
This self-directed learning can be one of the highest-ROI investments you make in your career.
Leadership isn't about waiting your turn—it never was. It's about making your own moves and strengthening your dynamic capabilities, entrepreneurial skillset and side hustle mindset.
Whether or not you ever launch a formal side hustle, you will need that mindset and those dynamic capabilities to succeed in the decades ahead.
And the good news is that a side hustle mindset is fully learnable and fully portable. Once you build it, no one, no organization, no downturn can take it away from you.
Hashtags
Try Our AI Features
Explore what Daily8 AI can do for you:
Comments
No comments yet...
Related Articles
Forbes
5 hours ago
- Forbes
Be Easy To Work With: The Overlooked Career Skill That Drives Success
A group of professionals collaborating effectively "Be easy to work with." That was the most impactful piece of advice my mentor gave me early in my career. I had just stepped into a challenging stretch role that required me to grow quickly, learn new skills and make a noticeable impact. Eager to succeed, I reached out to her because she was an experienced and accomplished leader. When we met, my primary question for her was, 'How can I make the right impression and thrive in this new position?' I expected her to say things like "leverage your strengths," "work hard," or "be yourself." All solid advice, but that's not what she said. Her response was simple, practical and powerful: "Be easy to work with." That insight has stuck with me. Over the years, I have seen it hold true not only in my career but in the experiences of countless professionals and leaders I've coached and developed. Regardless of role, industry or level, being easy to work with is an underrated but essential skill that strengthens collaboration, builds trust and drives long-term success. 5 Practices to Be Easy to Work With Backed by research and practical experience, these five practices have consistently helped professionals and leaders become more collaborative, trusted and effective across diverse roles and industries. 1. Focus on We Instead of Me Do the people you interact with to get work done believe that you understand and have their best interests at heart, or do they feel you are leveraging the situation for selfish gain? Trust will remain low if others perceive you as focusing only on your interests. To build trust, you must approach working with others with a self-orientation of "we" versus "me." Taking the time to understand others' perspectives, goals and solutions is the foundation for successful collaboration. People will almost always bring varying views about any complex situation that requires collaboration for success. Asking open-ended questions to understand how others perceive the work at hand is a crucial first step in finding shared meaning for collaborative work. To establish a "We" perspective, you must regularly ask two types of questions: 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝗧𝗼 𝗨𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱 𝗢𝘁𝗵𝗲𝗿' 𝗣𝗲𝗿𝘀𝗽𝗲𝗰𝘁𝗶𝘃𝗲𝘀 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻𝘀 𝗧𝗼 𝗚𝗲𝗻𝗲𝗿𝗮𝘁𝗲 𝗦𝗼𝗹𝘂𝘁𝗶𝗼𝗻𝘀 Taking the time to ask questions does not stop you from sharing your perspectives about the situation; it just means you choose to ask questions and understand others' views before sharing your own. 2. Deliver Results Credibility is built by consistently doing what you say and delivering quality work. I often see articles and posts that focus solely on the relational aspects of being an effective employee (such as kindness, empathy, listening and understanding), but do not give equal weight to the importance of delivering results. To build relationships and gain influence, people must believe you can and will get the job done. Consistency is a crucial aspect of reliability. Be someone others can rely on to get the job done. When you deliver on your commitments, trust is built. Establishing clear responsibilities, next steps and timelines enables people to rely on each other, whether meeting deadlines or fulfilling their duties. 3. Demonstrate Emotional Competence Our brains and bodies are hardwired to react when we feel threatened. This instinctive reaction is why many well-intentioned, skilled and competent individuals make poor decisions that negatively impact themselves and others. Understanding our physical responses to negative emotions helps us recognize when it's time to pause. Pausing allows our minds to catch up with our emotions before we react out of anger, fear, fatigue or frustration. Emotionally competent people do not blame circumstances or conditions for their behavior. During challenging interactions, establishing a long-term orientation by aligning our "in the moment" intentions to our longer-term goals and values helps us to: 4. Seek Feedback Regardless of your talent or level of effectiveness, you will have flawed perspectives or sometimes make mistakes. Asking team members, stakeholders or managers for their feedback demonstrates that you value their perspectives, have a growth mindset and want to continually improve. Since giving feedback feels risky for people, we must be deliberate about creating a safe environment by actively giving permission and expressing openness and desire to receive feedback about our performance. To regularly receive honest feedback, we need to minimize potential obstacles while encouraging others by: 5. Practice Reflection Reflection is a humbling yet powerful tool that helps us improve our performance. However, it is not easy, as it requires us to look honestly at ourselves, including our strengths, weaknesses and areas that need improvement. A practice of reflection often leads to insights, learning and ideas to test future experiences. Research shows that regular practice of reflection increases our capacity to demonstrate emotional intelligence, social skills and learning agility. Rolfe et al.'s (2001) reflective model is probably one of the simplest reflective models, as it centers on asking three straightforward questions: What? So what? Now what? This practical approach to reflection provides a framework for assessing experiences, making meaning of them and determining what they mean for future action. Below are some example questions for you to use to customize your reflection process: What? So What? Now What? Why You Should Be Easy to Work With Being easy to work with is often overlooked when professionals think about skill sets for advancing their careers and that is a mistake. No matter how high your level of technical skill, experience or intelligence, it will be your ability to effectively collaborate, communicate and adapt with others that will make the difference for long-term success. If you want to grow your influence, advance your career and build lasting professional relationships, start with this: Be easy to work with.
Forbes
7 hours ago
- Forbes
Remote Leadership That Sparks Innovation Across Distance
Boardrooms have vanished into Zoom boxes, and casual hallway chats are now emojis in Slack threads. But while some businesses are scrambling to regain control in a distributed environment, others are thriving — led by entrepreneurs who've found ways to transform distance into an engine for growth. These leaders aren't mimicking the office in digital form. Instead, they're redefining what strong leadership looks like when everyone is working remotely. By embracing clarity, structure, and human-first systems, they're proving that well-led remote teams can be more aligned, creative and resilient than their in-office predecessors. Here's what's working and why. 1. Structure weekly rhythms to drive focus For distributed teams, ambiguity is an inconvenience, but more importantly, it's a performance risk. Gian Reyes, vice president for marketing and strategic partnerships at KMC Solutions, emphasizes that consistent direction and feedback aren't optional. 'The real value comes from regular one-on-ones — that's where coaching, feedback and alignment happen in real time,' he says. KMC Solutions uses structured rhythms — Monday alignment meetings and Friday progress check-ins — to build urgency around solving real business problems. According to Reyes, this keeps employees connected to outcomes, not just outputs. It also reinforces a culture where people know how their work contributes to the bigger picture. 2. Recognize impact to maintain momentum When employees aren't in the same physical space, it's easy for good work to go unnoticed. Tyler Nielsen, marketing director at Avoya Travel, sees timely recognition as a key driver of motivation. 'Reinforcing that someone's work is seen and valued helps keep motivation high,' he says. Nielsen recommends making recognition personal and specific. Whether it's a shoutout in a team chat or a moment of acknowledgment in a one-on-one, tying praise to impact helps team members feel aligned with outcomes, not just busywork. Research supports this: employees who feel recognized are significantly more likely to be engaged and stay with their company. 3. Use short-term squads to encourage innovation Solving complex problems remotely requires more than assigning tasks. Gian Reyes, vice president for marketing and strategic partnerships at KMC Solutions, describes how his team forms small, cross-functional 'task forces' to tackle high-impact challenges. 'These aren't standing committees,' he says. 'They're mission-driven squads with a clear objective and a short timeline.' This structure gives team members a chance to contribute beyond their formal roles and fosters faster, more focused collaboration. A 2025 report by Boston Consulting Group on the world's most innovative companies reinforces this approach. It found that firms embracing flexible, cross-functional team models are significantly more resilient and more effective at innovation, particularly during periods of uncertainty. These agile squads allow organizations to bypass the bottlenecks of traditional hierarchies and accelerate both decision-making and creative problem-solving. 4. Redesign onboarding for belonging, not just logistics Remote onboarding often becomes a checklist—but without connection, new hires can feel isolated. To address this, some organizations are designing onboarding experiences that prioritize belonging from day one. According to MIS Quarterly Executive, Accenture's New Joiner Experience (NJX) — which features immersive virtual environments like the One Accenture Park campus — has engaged over 400,000 employees as of December 2024, with participants consistently rating the experience above 4.6 out of 5. That scale and sustained satisfaction demonstrate that immersive, culture-focused onboarding can significantly elevate early employee sentiment and engagement. Leading organizations now include structured introductions with multiple team members, walkthroughs of decision-making, not just procedures, and a clear roadmap for the first month. These elements reinforce understanding of company values and help embed new hires into the organization's culture from day one. When remote work is approached with intention, it can surface the best in teams; greater autonomy, more innovation, and tighter alignment with outcomes. That doesn't happen by default. It takes clarity, culture, and consistent effort from leadership. But for those willing to reimagine what leadership looks like from a distance, the rewards aren't just survival; they're scalable, distributed success.
Yahoo
7 hours ago
- Yahoo
‘Shark Tank' icon Kevin O'Leary reveals the 3 things he looks for when investing his millions into a founder
Multimillionaire investor Kevin O'Leary looks for three star qualities in the entrepreneurs he goes into business with: those who have a 'founder's mindset,' a balanced talking-to-listening ratio, and executional prowess. From working with the likes of late Apple cofounder Steve Jobs and multimillion-dollar entrepreneurs to being an investor on his hit-TV show, he's picked up a few patterns of the most successful people. Multimillionaire entrepreneur Kevin O'Leary knows a thing or two about picking the right people and ideas to invest in. Having worked with greats like Steve Jobs, not to mention his success on Shark Tank backing businesses generating millions, he's picked up on a few key qualities in great founders. O'Leary looks for three qualities in the people he chooses to do business with. The 71-year-old investor tells Fortune the most critical trait is having 'founder's mindset': adopting a frame of mind that prioritizes 'signal,' or what has to get done in the next 18 hours, while drowning out the 'noise' of everyday life and complications. He witnessed this demeanor while working with Jobs, when Apple was partnering with O'Leary's $4.2 billion software company SoftKey Software Products. He requires that the founders he invests in have that same leadership ethos—even if it's a quality that's hard to come by. 'The ability to see all the noise coming at you and filter it out, and focus on the three to five things you're going to get done, that's a remarkable attribute,' O'Leary tells Fortune. 'You find that in 30% of the people. Then you want to back those people, because if they're not successful in their first mandate, they're going to figure it out. That attribute is very important.' When it comes to the signal versus the noise, he currently operates on a 80:20 balance, just like Jobs did while running Apple, and looks for entrepreneurs who can keep their eye on the ball. O'Leary admits that he didn't always have the right ratio in embodying the founder's mindset—but now has achieved it, and looks for it in others. 'You have to decide everyday, every 18 hours, what three to five things you have to get done,' O'Leary says. 'It's not the big vision. It's what you have to get done in the next 18 hours that matters.' The two other traits a founder needs to have O'Leary's backing O'Leary has heard hundreds—if not thousands—of entrepreneurs plead their business case while starring on Shark Tank. Thanks to his intuition from decades in the game, he's worked alongside and invested in a lot of winners. In 2014, O'Leary put $150,000 down for 80% of licensing profits of small photo-book subscription service Groovebook, which was later bought by Shutterfly for $14.5 million, making it one of the show's biggest acquisitions. He also had luck with sustainable cleaning-products business Blueland, investing $270,000 for 3% equity and $0.50 per unit royalty until principal was recouped. By 2022, Blueland made over $100 million in lifetime sales and profitability, with its products now flying off the shelves of Target and Whole Foods every 10 seconds. It's clear the serial investor has developed a keen eye for what will work well. In addition to the 'founder's mindset,' the serial investor also emphasizes the importance of having a balanced listening-to-talking ratio and strong executional skills, which he says is 'impossible to find.' He says he didn't always get the talking-to-listening balance right. Wall Street and Silicon Valley executives may think they should be the loudest and most outspoken people in the room—but taking a backseat and giving others the floor is important, too. Not enough listening and too much talking may stifle great business ideas that get drowned out. 'Reverse the ratio of talking and listening. Most people love to hear themselves talk—I was guilty of that for years, and I've reversed it,' O'Leary says. 'I listen two thirds of the time, and I talk one third of the time. That's my new ratio, and it's much more powerful.' Lastly, the baby boomer investor looks for unparalleled executional skills. Coming up with the next billion-dollar business venture is one thing, but getting it off the ground is another. O'Leary looks for founders and teams that can get the job done—even if it takes more than one try. Being an excellent executor doesn't always mean hitting a home run your first time at bat. Sometimes, O'Leary says, investors and entrepreneurs need a little karma and luck. 'Great ideas are dime a dozen—executional skills are impossible to find,' O'Leary continues. 'I've invested in lots of teams over the years that screw up their first deal, they go to zero, and then I invest again, and I get a huge hit, because I know they're good. 'I'm working on a deal right now with a team that I just finished a great execution with, and hopefully will be good on the second one. I like to work with people that I know have proven executional skills.' This story was originally featured on Error in retrieving data Sign in to access your portfolio Error in retrieving data Error in retrieving data Error in retrieving data Error in retrieving data
