How to Challenge Yourself as an Entrepreneur: 12 Fail-Proof Tips


They say that life is about the journey, not the destination—and many seasoned entrepreneurs will tell you the same goes for starting a business. As a business owner, you might recall the (quite literal) blood, sweat, and tears that went into turning your great idea into a booming business. 

While there may have been long nights where you questioned your sanity for letting yourself start a business in the first place, hopefully you’ve been able to look back on the experience and appreciate just how much you’ve grown from the challenges you’ve faced. 

Now that you’ve hit your business goals and targets, you may have found yourself thinking about what’s next. If you’re ready to take yourself and business to the next level, begin by challenging yourself to go outside your comfort zone. Challenging yourself and your business could open the door for long-term and continued success, improved health, and potential new revenue streams. 

Read on for more tips on how to challenge yourself as an entrepreneur, or skip to our infographic for tips on how to challenge yourself and keep growing both professionally and personally as an entrepreneur. 

1. Become an Expert


If you’re looking for a new goal to work towards, consider pushing yourself to be an expert in your space. Having the expertise and knowledge to make pivots or quick calls for your business is a key component in being a successful business owner long-term. 

That being said, becoming an expert in any field will take some time and a diverse portfolio of experience. So, start with achievable micro-goals, such as making your knowledge and business expertise available to your network, or applying to speak at a business conference. 

You could also read entrepreneurial books, take a class, or work towards a certification that will help you become more knowledgeable in the world of business.

Pro Tip: Reach out to an industry expert you admire and ask them how they became a thought leader in the space over coffee or during a quick phone call. 

2. Teach Others

Do you ever wish you knew what you know now when you were first starting out? There are plenty of small business owners who are beginning their entrepreneurial careers who need guidance. Take on the role of a mentor or business consultant for small business owners seeking credible advice from someone who’s been there. 

Meeting with young entrepreneurs face to face, starting a business podcast or blog, or even writing a book are great ways to disseminate your valuable learnings—and could all generate new  streams of revenue down the line. 

Pro Tip: Take to social media to fill business knowledge gaps with your own expertise, in an easily digestible way for your followers. 

3. Create an “Impossible” Goal 

We’ve all heard of stretch goals, or goals that are achievable if you put in the extra work, but maybe it’s time to think bigger. If you’ve been feeling unmotivated, try making an “impossible” goal. This could be a goal, either personal or professional, that seems impossible to achieve in the foreseeable future. However, if you continue to stay on track and take steps forward in your business, you could achieve this in the next few years. 

Without an impossible goal, you might not push yourself as hard as you would if you only had a stretch goal or a more realistic short-term goal.

Pro Tip: Double your yearly revenue target to create your impossible goal! 

4. Surround Yourself With Smart People


Don’t be afraid to be in a room with people who know more than you do. A great business starts with even better people, so hire people who know more than you do about a certain area of your business, and who are able to provide feedback as needed. They could push you to make decisions and take risks that you may not have considered before. 

You could also consider joining a business association, where you can connect with like-minded entrepreneurs who will give you access to their knowledge and business learnings. This is a great way to stay knowledgeable about the business community. It also gives you an opportunity to build relationships, brainstorm and troubleshoot with like-minded peers. 

Pro Tip: Improve your access to knowledgeable entrepreneurs and influential business professionals all over the world by joining an online business community.

5. Ask for Feedback

When it comes to your business, don’t forget about customer, client, and employee feedback. Don’t know where to start? There are several effective ways to get feedback from your customers. You could implement a live chat, run a survey or poll on social media, monitor reviews and comments, and more.[1] 

Feedback from customers, other business owners, or employees can be one of your most valuable tools, so don’t be afraid to ask for it. Then establish trust by pushing your business forward to accommodate those needs. 

Pro Tip: Follow up with your customers or clients with a quick and easy email or text survey to see how they felt about their experience, product, or service. 

 6. Learn to Become a Better Leader

Is there an area of leadership that you might need to improve upon? Maybe you find it difficult to have tough conversations with employees or business partners, or you’d like to have more confidence to make real-time business decisions. 

Whatever it is, as a leader in your business, you should always set an example and push yourself to be better, and inspire your employees to do the same. Consider studying up on leadership resources or familiarize yourself with different tools that can help you be a great leader and manage others effectively. 

Pro Tip: Make a list of the top three leadership skills you want to learn this year. Then create a game plan with actionable steps you can take to achieve these over the next few months. 

7. Improve Your Physical and Mental Health

A recent report done by the Canadian Mental Health Association (CMHA) and Business Development Bank of Canada (BDC) surveyed close to 500 entrepreneurs and revealed that 62% of business owners feel depressed at least once a week.[2] 

Potential reasons for entrepreneurs experiencing dark moods could range from having a preexisting mental health condition, having feelings of anxiety or uncertainty about business decisions, or fears of potential failure or inadequacy. 

A great new challenge or goal to consider could be one that improves your mental or physical health—which tend to go hand in hand. For instance, maybe you’d like to focus on exercising each day, which will in turn help you deal with stress or any triggers that could affect your mental health the following day. 

We know your business is a big part of your life, but make sure you’re making yourself your biggest priority. Create a fitness goal for yourself or make a commitment to practice meditation, mindfulness, or your version of self care each morning or night.

Pro Tip: Start your morning doing something for yourself, rather than your business. This could be journaling, a quick workout class, or enjoying your favorite cup of coffee in silence.

8. Learn a New Language


Entrepreneurs should always think about the next opportunity—and maybe it’s bringing your business to a new target audience or region. In addition to improving your networking and simplifying international business relations, learning a new language has proven to have several great benefits when managing your business. 

People who learn a new language tend to develop better memory, creativity, self confidence and improved decision making skills—all of which could greatly benefit your business.[3] Additionally, a study found that 89% of clients find it valuable to work with bilingual people.[3] There are several different online courses available for you to learn a new language from the comfort of your desk, home, or car. 

Pro Tip: While you’re broadening your knowledge of language, consider increasing your understanding of business and finance terms in your native tongue, as well. 

 9. Break a Bad Habit

When it comes to challenges, breaking old habits and improving oneself could be the most challenging of them all. Is there something that you do regularly that in the back of your mind you know you need to change? It may not be directly related to your career or business—and that’s okay, because becoming the best version of yourself will ultimately improve your business. 

Habits are tough to break because they fall under our comfort zone. You will have to literally train your mind to do something different and create a new routine. Start with small steps each day. 

Pro Tip: Instead of breaking a habit and leaving behind a void, start with replacing your bad habit with a better, more beneficial one.

10. Give Back

Make time to give back to your community, or an organization that you’re passionate about. Once you’ve found the cause, commit yourself, and maybe your employees, to a certain amount of hours of volunteer time each quarter. 

Volunteering is a great way to grow as a community and as a team, and there are many benefits that can directly affect your business from giving back as well. More and more businesses are incorporating philanthropy into their quarterly goals because it can improve the community, increase employee morale, improve marketing for an organization, and make a business qualify for tax deductions. 

Pro tip: Get inspiration from top corporations who are doing it right, to see how they incorporate philanthropy into their company’s core values.

11. Improve Your Sleep Routine


Do you find yourself tossing and turning or lying awake in the middle of the night, worrying about your to-do list for the next day? As an entrepreneur you may be like the one in three adults who suffer from sleeplessness.[5] 

Improving your sleep will improve your ability to learn new things, handle stress, and be more productive with your everyday tasks. In fact, lost productivity related to poor sleep is estimated to cost the United States $411 billion a year.[6]

Pro Tip: Create a nightly sleep routine. This can include going to bed at the same time each night, unplugging from electronics before bed, or taking a warm bath before jumping in the sheets

12. Try Something New

If none of the above pique your interest, try something new—like starting or buying a new business, expanding on your current business, entering a different market, or even beginning a new hobby. Remember the same drive you had to start your business and use that to build on what you’ve made or start another passion project. 

Some of the qualities that make entrepreneurs so successful are fearlessness and the ability to take risks and try new things. If you’re lacking the motivation that gives you your entrepreneurial spirit, we recommend you take some time to brainstorm a project that you’re excited about and are willing to push your limits for. 

Pro Tip: If you’re not ready to start a brand new business endeavor, make it a priority to try one new outdoor adventure, recipe, or hobby each month! 

What Does It Mean to Challenge Yourself?

Every time you challenge yourself, you’re making the choice to push yourself mentally or physically outside of your comfort zone and enter uncharted territory in order to achieve a difficult, but realistic goal—which can be pretty intimidating. So why do it? 

People should continually push their limits and challenge themselves. That’s what motivates successful individuals to do amazing things that they never expected to do—like run marathons, make new scientific discoveries, or even start their own business


Infographic Sources:

National Center for Biotechnology Information | Nielsen | Inc.

Article Sources:

  1. “8 Effective Ways to Get Customer Feedback
  2. “Going it Alone: The Mental Health and Well-Being of Canada’s Entrepreneurs
  3. “Top 10 Benefits of Learning a New Language
  4. “Do All Your Employees Speak the Same Language?
  5. “1 in 3 Adults Don’t Get Enough Sleep
  6. “Why Sleep Matters – The Economic Costs of Insufficient Sleep
Founding Editor and VP at Fundera at Fundera

Meredith Wood

Meredith Wood is the founding editor of the Fundera Ledger and a vice president at Fundera. 

Meredith launched the Fundera Ledger in 2014. She has specialized in financial advice for small business owners for almost a decade. Meredith is frequently sought out for her expertise in small business lending and financial management.

Read Full Author Bio