Everything I Learned Cultivating An Entrepreneurial Mindset: How to Overcome Challenges, Set Goals, and Build Your Dream Business

If you want to know the secret to honing confidence as an entrepreneur, here it is: Starting a successful business isn’t just about having a groundbreaking idea, the perfect timing, all the resources in the world, or even a whole lot of money. It’s also about having the right mindset to navigate the highs, the lows, and the inevitable plot twists.

The way you think, adapt, and push through challenges does determine whether you’ll thrive or throw in the towel. That said, how you cultivate your entrepreneurial mindset is based on a plethora of things; those factors will shift as you grow your business. In this post, I’ll break down what it really means to think like an entrepreneur, how you can channel your potential (without the fluff), and I’ll offer some inspiration to hopefully motivate you to lean into your entrepreneurial mindset way more this year.

Table of Contents:

To start, I think it’s worth clearing up a misconception you’re likely already forming: That the entrepreneur mindset is entirely specific to hard-boiled entrepreneurs. This, my dear reader, is entirely wrong.

Here’s my rebuttle: Anyone (yes, even you) can demonstrate it. Even if you haven’t quite figured out every moving part of your business yet. Even if you haven’t written down every detail about how you’ll make your ideas tangible. Whether you’re an employee looking to start taking that passion project you had seriously or a freelancer that’s ready to turn your talents into something bigger, embracing your entrepreneurial mindset will empower you to:

Think creatively
Solve problems proactively
Seize opportunities

At its core, an entrepreneurial mindset is about fostering a solution-oriented approach to challenges, no matter how difficult they are. Even more so, honing your entrepreneurial mindset means developing strategies to take on whatever comes your way and building a tolerance for pushing through setbacks. After all, success isn’t about never failing; it’s about how you get back up.

If you’re interested in cultivating this way of thinking, check out the following section for a breakdown of the key characteristics you can expect to develop as you progress.

Entrepreneurial Mindset Characteristics

Locking into your entrepreneurial mindset starts with embracing a growth-oriented perspective. Before you even think about solidifying a business strategy or securing a grant, you’ve got to train your mind to see things differently. By differently, I mean reframing your attitude around encountering the hard stuff as you navigate your journey toward becoming an entrepreneur.

No one starts with all the answers on how to do this, but I’ll tell you one thing: You can shift your mindset by making little changes, starting with how you think. Check out a list of characteristics I put together to help you establish a strong foundation and confidently tackle challenges:

1. Self-Drive

As an entrepreneur, you should aim to be self-driven. Why? Because you’re solely responsible for your business’s success. You need to motivate yourself and push through obstacles without anyone telling you what to do and when to do it.

The great thing about self-drive is that it can look like anything, from staying focused on your goal (as entrepreneurship can require long hours, hard work, and dedication) to seeking new opportunities and learning experiences. Being self-driven allows you to take initiative and make decisions that will move your business forward, even when uncertain.

2. Flexibility

As an entrepreneur, you have to be open-minded about approaching your work … it comes with the territory if you will. Whether it be willing to pivot when necessary, working with diverse groups of people, or listening to critiques, you’ve got to be willing to adapt, learn, and evolve based on new information and feedback.

By staying flexible, you can adapt to change and take advantage of opportunities as they arise, instead of letting them pass by.

3. Creativity

To think like an entrepreneur means you have to get creative. Many people like the sound of running their own business but need more creativity to develop the solutions and strategies required to gain and retain a customer base.

Plus, even if you’re not serving a “creative” industry, your choices — from your supply chain to your marketing — can capture your target audience’s attention. Everything you’ll do will be assessed against your competitors, so you’ve got to come correct with a unique value proposition, compelling branding, and innovative problem-solving that sets you apart from everybody else.

4. Authenticity

Authenticity is one of the most challenging qualities to maintain as an entrepreneur. With all the industry noise and trend-chasing hoopla, staying true to yourself, your brand’s mission, and, most importantly, your customers is hard, to say the least.

However, staying committed to authenticity builds trust and creates a strong connection between you and your customers. When you’re true to yourself, your customers are likelier to trust you and feel engaged with your business.

5. Tenacity

According to data from The Hustle’s 2024 Entrepreneurship Trends Report, only 28% of businesses are profitable within their first year of starting; 36% are super profitable within two years of operation.

What does this data tell us? Well, in short, it proves that entrepreneurs have to have the tenacity, or determination, to keep trying if they want to see the results they’ve dreamed of. Going through setbacks (i.e., low sales or lack of brand visibility) can chip away at your confidence, but true entrepreneurs understand that the climb to success isn’t free of challenges, so no matter what comes your way, you’ve got to see all of it through.

Employee vs. Entrepreneur Mindset

Individuals who acquire the entrepreneurial mindset — or entrepreneurial spirit — will do what others won’t: They take initiative and make a point to create opportunities rather than wait for them. They embrace leadership opportunities and learn what they can at every possible turn. Those qualities — among others — set the entrepreneurially minded apart from, well, those who just aren’t. I like to call those folks “employee-minded.”

Here’s some insight into the key differences between the two thought processes:

1. Entrepreneurs zero in on individual tasks more than employees.

Argue with me if you want to, but ‘multitasking’ isn’t a thing. It’s a buzzword that means rapidly jumping from individual task to individual task, which ultimately implies sacrificing some level of quality and thoughtfulness along the way.

But if there’s one thing entrepreneurs know how to do without fail, it’s focus. As an entrepreneur, you learn that deep, intentional work consistently outperforms scattered effort. Plus, success doesn’t happen because you do everything at once. It coalesces when you’ve learned what’s deserving of your attention. Prioritization, not multitasking, moves the needle forward, my dear reader.

2. Entrepreneurs have an ‘on to the next one’ mentality.

Employee-minded folks are known to get fixated on their mistakes; entrepreneurs breeze by ‘em.

You see, a good entrepreneur sees the good in failure. To unlock your entrepreneurial mindset properly, you must understand that every mistake is a learning experience. You have to confidently know that the world isn’t over with every screw-up … and be able to quickly derive lessons from any that may take place. This may take some time, but once you’ve uncovered a strategy that works for you, you’ll have a solid approach to managing missteps.

3. Entrepreneurs partition and prioritize their work differently.

When employees apply themselves to something, it isn’t a problem. What typically causes issues is how they use their time and energy. Some folks prefer to tear through all their work as it comes to them, others like to pace themselves through different tasks, and some choose to just plain ol’ procrastinate.

On the other hand, entrepreneurs often use a different method. Oppositely, they make a point of working smarter and are skilled at partitioning their work thoughtfully. They know that time is the most essential professional commodity, so they handle it with tact.

4. Entrepreneurs are wise about risks and confront them head-on.

Employee-minded individuals have a reputation for being risk-averse. They value stability, which is totally understood, but they may lack a nuanced understanding of what it takes to go above and beyond for long-term growth and innovation. Entrepreneurs, however, know to expect moments when their business priorities will have to take precedence over their work life, personal life, and, yes, their sleep schedule.

Entrepreneurs take calculated risks and anticipate having to take a leap of faith at some point in their business growth process. The key difference here is a matter of mindset. Entrepreneurs know what comes with the territory of their dreams; employee-minded folks are known to seek the comfort of structure and, to some degree, predictability.

5. Entrepreneurs aren’t threatened by people more intelligent than them.

You’ve probably heard the old saying, “If you’re the smartest person in the room, leave that room.” For some employee-minded individuals, that phrase presents … a tricky concept. For entrepreneurs, it emphasizes valuing learning opportunities more than ego.

As an entrepreneur, nurturing a good sense of humility will help you realize your ambitions and bolster your professional skill sets.

6. Entrepreneurs own all their decisions — good and bad.

Some employee-minded people may deflect responsibility for the consequences of their actions entirely, but here’s one thing you can expect while pursuing entrepreneurship: You’ll have to hold yourself accountable for poor decisions as much as you tout your accomplishments. There’s no trying to avoid blame, no distancing yourself from any less-than-ideal calls you make; this accountability comes with the beauty of being your boss.

As I’ve mentioned, entrepreneurs view screw-ups as learning experiences that don’t define them or dictate their professional value. Take your shortcomings on the chin and keep moving forward.

Pro Tip: My advice for preventing stressful business things before they happen? Create a business plan that outlines everything, from your business name to how you’ll pitch your business to investors. I recommend using HubSpot’s Business Startup Kit if you want to organize your thoughts with easy-to-follow, easy-to-share templates.

How to Develop the Entrepreneurial Mindset

When folks bare their “secrets” about adopting the entrepreneurial mindset, they don’t share how nonlinear the journey really is. The road map to get there is paved with tons of vague instructions. Folks will say, “Be fearless, work hard, take risks,” but they don’t provide the concrete steps or how-to guidance that help others make it happen. But lucky for you, my dear reader, I’m not like those people. Instead, I’ve written the complete playbook to tapping into your entrepreneurial mindset.

Here’s every actionable step you should take to engage your entrepreneurial mindset in day-to-day life, no holds barred:

1. Set clear goals.

First thing’s first: You can’t make progress as an entrepreneur if you don’t know which direction you’re going in; at this stage, having dreams or wishes is not enough. You need clear goals.

Start by outlining a handful of SMART goals to hit each week or month, ones that are:

Specific
Measurable
Attainable
Relevant
Time-bound

Chip away at them every day and see how far you can get. If you have trouble staying accountable, write your goals down or share them with family, friends, colleagues — hell, even your LinkedIn network. Remember: Big achievements are often the result of small, consistent actions. Don’t get caught up in perfection; moving forward is all that matters.

2. Prioritize learning.

When discussing “learning,” you probably picture it super formally, like completing a training or certification. Now, don’t get me wrong. Formal learning is vital for professional development, and you shouldn’t pass up on those kinds of opportunities … but you can also learn by simply listening to others in a way that works for you.

Don’t hesitate to ask questions fueled by curiosity. Seek out a mentor, read an expert-backed article, message a peer on LinkedIn, listen to motivational podcasts, take an online course. People who have done what you’re doing have the wisdom to share; don’t miss any chances to get the answers and resources you need.

If it helps, technically, I didn’t even come up with this — Jim Rohn, the late entrepreneur and author, did. He once said, “Formal education will make you a living; self-education will make you a fortune.”

3. Reframe failure.

Here’s a not-so-shocking statement: Failure doesn’t feel good. It likely won’t ever feel good. But the best entrepreneurs know that failure, rejection, risk, and criticism are all part of the gig, and choose to see them as common side effects of ambition. Instead of folding under pressure, a good entrepreneur learns to keep moving.

The key word here is to learn, since reframing your mindset around failure takes time and effort. The trick is not to think of failure as something to fear or avoid but, rather, a tool to understand situations better and make more informed decisions in the future.

A different perspective can entirely change your growth trajectory, so choose yours wisely.

4. Embrace risk-taking.

Here’s something you probably didn’t expect to hear from me: Failure is the best teacher.

When you take a risk, you either a) win or b) learn a lesson. This doesn’t mean you should spontaneously quit your job or say “yes” to the next opportunity that comes across your desk (or your Gmail? Maybe? Who knows these days). My point is, my dear reader, it’s all about calculated risk.

A calculated risk is a carefully considered decision with a degree of risk and a reasonable chance of a positive outcome. For instance, it’s common for entrepreneurs to put some of their personal assets on the line to finance operations. Yes, this is risky, but if you can get past the initial fear of such a risk, many benefits can await you on the other side.

Entrepreneurial Mindset Quotes

Sometimes (especially depending on the day you’re having), motivation doesn’t come from within. Sometimes, motivation comes from hearing someone else’s take on success. Or struggle. Or just trusting the process. My point is this: It helps to hear someone else’s take on how they made things happen when things got tough.

Whether you’re looking for an alternative view on resilience or just need a pick me up, here’s a curated collection of quotes I put together that I hope helps you see the entrepreneurship grind in a slightly different light:

On Perseverance

“Every no gets me closer to a yes.” — Mark Cuban
“Success is the sum of small efforts, repeated day in and day out.” — Robert Collier
“Life keeps throwing me curve balls and I don’t even own a bat. But my dodging skills are improving.” ― Jayleigh Cape
“Success seems to be largely a matter of hanging on after others have let go.” — William Feather
“The difference between a successful person and others is not a lack of strength, not a lack of knowledge, but rather a lack in will.” — Vince Lombardi

On Work Ethic

“Be true to your heart, and if you’re passionate about your dream, work towards it. But don’t allow your idea of how you think it should manifest to prevent what’s actually unfolding from happening.” — Keke Palmer
“Success isn’t owned. It’s leased, and rent is due every day.” – J. J. Watt
“So often people are working hard at the wrong thing. Working on the right thing is more important than working hard.” — Caterina Fake
“I hated every minute of training, but I said, ‘Don’t quit. Suffer now and live the rest of your life as a champion.’” — Muhammad Ali
“I never dreamed of success. I worked for it.” — Estee Lauder

On Taking Risks

“Go out on a limb. That’s where the fruit is.” — Jimmy Carter
“Don’t be afraid of the answers. Be afraid of not asking the questions.” — Jennifer Hudson
“Progress always involves risks. You can’t steal second base and keep your foot on first.” — Frederick Wilcox
“Everything is a risk. Not doing anything is a risk. It’s up to you.” — Nicola Yoon
“Rarely are opportunities presented to you in a perfect way. In a nice little box with a yellow bow on top. Opportunities – the good ones – are messy, confusing and hard to recognize. They’re risky. They challenge you.” — Susan Wojcicki

On Handling Failure

“I don’t like to lose — at anything — yet I’ve grown most not from victories, but setbacks.” — Serena Williams
“Never confuse a single defeat with a final defeat.” — F. Scott Fitzgerald
“It’s fine to celebrate success but it is more important to heed the lessons of failure.” — Bill Gates
“Failure is only the opportunity to begin again, this time more intelligently.” — Henry Ford
“You may encounter many defeats, but you must not be defeated. In fact, it may be necessary to encounter the defeats, so you can know who you are, what you can rise from, how you can still come out of it.”― Maya Angelou

On Motivation and Drive

“Successful people keep moving. They make mistakes, but they don’t quit.” — Conrad Hilton
“The question isn‘t who’s going to let me; it’s who is going to stop me.” — Ayn Rand
“Challenges are gifts that force us to search for a new center of gravity. Don’t fight them. Just find a new way to stand.” — Oprah Winfrey
“Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.” — Steve Jobs
“No matter how many goals you have achieved, you must set your sights on a higher one.” — Jessica Savitch

On Leadership

“To become truly great, one has to stand with people, not above them.” — Montesquieu
“Leaders think and talk about the solutions. Followers think and talk about the problems.” — Brian Tracy
“The ability to learn is the most important quality a leader can have.” — Padmasree Warrior
“Leadership is a series of behaviors rather than a role for heroes.” — Margaret Wheatley
“Do it from the heart or not at all.” ― Jeanette Winterson

Entrepreneurial Mindset Examples

In my experience of chasing big goals, it’s always been helpful to see people who’ve made their dreams plausible and attainable regardless of the odds they faced. I think it could benefit you, too, my dear reader.

Check out these folks whose entrepreneurial mindset took them pretty far:

1. Alicia Scott — Range Beauty

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Believe it or not, Alicia Scott — Founder and CEO of Range Beauty — started her ance-safe and eczema-friendly makeup business with only $150. After appearing on Shark Tank and securing a deal with Lori Greiner, Scott’s makeup brand became the first-ever Black woman-owned beauty brand to receive funding from the show. Since then, Range Beauty has relaunched, received a Glossier Alumni Award, and is now being sold nationwide at Sephora. Still, none of its success happened overnight; as a matter of fact, her company is still growing.

Alicia’s commitment to trusting her process, taking as much time as needed to do fundamental research, and refining her business truly reflects her entrepreneurial mindset. In an episode of The Foundr Podcast, Alicia admitted that it took three years to fully ideate and build Range Beauty into what it is today; she even mentioned that she bootstrapped her first product batch. “I moved to Atlanta, Georgia, worked a 9 to 5, made sure all of my expenses and personal bills were taken care of, but whatever residual income I had after my paychecks, that’s what went toward building Range Beauty,” Scott shared.

Range Beauty’s climb to success is still in progress, so there’s much to learn from Scott’s entrepreneurial mindset. Here are the takeaways I’ve extracted that I think could apply to you:

Be prepared to go back to the drawing board. Scott shifted Range Beauty’s brand identity and vision several times before landing on something that felt authentic to the business and product she was developing.
Expect setbacks and handle them with grace. Alicia received a cease-and-desist letter regarding a former tagline for Range Beauty; she revealed she was happy about it, too. Although the cease-and-desist may have delayed Scott’s business expansion, she reframed the situation as an opportunity to spend more time ironing out her brand’s niche.
Do it all by yourself until you can’t anymore. When Alicia began fulfilling orders for Range Beauty, she boldly confessed to utilizing every room in her apartment to create products and get them out to customers. As an entrepreneur, you’ll likely want everything you need to start your business right away, but the reality might be that it could take a while to get there. Don’t feel ashamed about getting DIY if it means getting started.

2. Creator Tea Talk/Em Dash Co. – Jayde Powell

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According to CNBC Make It, Jayde Powell — who only recently began her career as a full-time creatorpreneur and founder of two content and creative development-focused ventures — made $27,000 by leveraging her voice through LinkedIn and social media content creation.

I spoke to Jayde a few months back to pick her brain about what encouraged her to quit her 9 to 5 and pursue her solopreneurship as a round-the-clock gig; here are my takeaways about Jayde’s entrepreneurial mindset that I think are worth sharing:

Invest in continuous learning as much as you can. Jayde shared that entrepreneurs should “level up their skills” whenever possible. As an entrepreneur, you should always be thinking about ways to elevate your offerings and how to appeal to new clients.
Accept that entrepreneurship is fluid. Your goal may be to scale your business to a multi-billion dollar company; you could also not have this goal, which could completely change how you view milestones and success. Regardless of how you want to grow, know that your perception of “making it” may not look like what you’ve seen from other big-name business owners or companies.
Don’t let optics rule decision-making around your business. Jayde’s biggest piece of advice? Craft an entrepreneurship experience that is specifically tailored to you and your dreams. Entrepreneurship can be whatever it needs to be to suit the needs of your life and the timeline you’ve set for yourself.

Anyone Can Have An Entrepreneurial Mindset

You don’t necessarily have to self-identify as an entrepreneur to exhibit “the entrepreneur mindset.” Heck, most entrepreneurs don’t until they’ve been in the game for a decent amount of time. However, no matter where you stand in your business growth process, know that embracing the entrepreneurial mindset is a tool for preparing for future successes.

Lastly, I’ll leave you with this:

All unexpected twists and turns aren’t bad; they often indicate progress.
Take risks. Risks invite opportunities, and opportunities open doors to advancement.
Starting your “side hustle” plants a seed for bigger things to come. And — in the words of the incredibly awesome Victoria Monet — when you want something, the only thing between you and your goals is time.

Editor’s note: This post was originally published in March 2021 and has been updated for comprehensiveness.