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4 Small-Business Challenges Every Leader Faces (and How to Overcome Them)

Ever heard of a successful business owner operating with the attitude, “Maybe I’ll succeed or maybe I won’t”?

No way! Successful business owners are in it to win it every day. They’re hustling to overcome the next challenge and keep moving forward. So what do you do when you want to keep growing your business but you’re worn out, discouraged and stuck no matter how hard you try to find a clear path forward?

Start by taking a quick a breather. Small-business challenges are normal. Every successful business leader hits walls. But to grow your business, you’ve got to bust through them. Which leads to what comes next. You’ve got to understand the four biggest challenges you’re up against and make a plan to overcome them. Let’s walk through those challenges and solutions now.

Small-Business Challenge #1: Not Knowing What to Do Next in Your Business

In the early stages of business, you get a pass if you’re flying by the seat of your pants. After all, you’re working hard and learning so you can make your business vision a reality. But if you’re just working to stay afloat year after year with no idea what’s working and what’s not, you’ve got a problem. Nothing kills a business like a leader without a plan.

Being tapped out on the strategy and skills to grow your business is what leadership expert John Maxwell calls the Law of the Lid. The Law of the Lid says you can only grow to the point of your highest skill level or leadership ability. So if you’re doing everything you know to do to get ahead and aren’t moving forward, it could be time to follow a new system that will stretch you and help you grow.

Small-Business Solution #1: Follow a proven system that gives you clear direction.

To understand what it means to push past your lid, think about an area of life where you or someone you know took a big leap forward—maybe getting out of debt, running a 5K, or dropping a pant size. Did a genie pop out of a bottle and grant a wish? Heck no! You followed a plan that worked. People rave about systems like Ramsey’s 7 Baby Steps, Couch to 5K and WeightWatchers because they’re built on making consistent, small wins that become big wins over time. Getting a plan for your business is much the same. Here’s what this boils down to for you:

  • Tap into your passion for your mission.
  • Be determined to achieve it.
  • Find a proven system to reach your goals and work it.

James Clear, author of Atomic Habits, writes, “Goals can provide direction and even push you forward in the short-term, but eventually a well-designed system will always win. Having a system is what matters.”1

Spoiler alert: The EntreLeadership System is the road map that’s guided thousands of small-business owners through the 5 Stages of Business, using the 6 Drivers of Business to reach their goals.

Small-Business Challenge #2: Leading People

Chances are, one reason you got into business is to be your own boss—but not necessarily to be somebody else’s boss. Then you realized you could only get so far by yourself. Now you’ve either got a team to help you grow or know you need one.

The thing is, people are your biggest blessing in business, but they’re also your biggest challenge. Team members present personnel issues, drama issues, company culture issues . . . you get the picture. So how do you bring out the blessings and reduce the challenges?

Small-Business Solution #2: Learn to be a leader, not a boss.

Before your business can grow, you have to grow as a leader. Notice we didn’t say you have to grow as a boss. Bosses push their employees. They use orders and fear to get things done. Nobody thrives under commands and threats. But leaders pull. They raise team members to a higher level and inspire them to achieve goals and do work that matters.

So challenge yourself to develop as a leader constantly. Here’s how:

  • Always be learning. Give yourself permission to learn from others. Take a class, listen to podcasts, and work through a list of top business and leadership books.
  • Be around other leaders and business owners who inspire you. Ask yourself who you want to connect with, and be intentional about who gives you advice, encouragement and accountability.
  • Invest in being coached. A good business or leadership coach will help you see what’s holding you back and help you get unstuck.
  • Develop your team. That’s right, as you help your team members grow, you’ll become better and stronger too.

Wondering how all this personal development leads to a stronger business? As you become a better leader, you’ll communicate more effectively, handle conflict better, and set the tone for a healthier company culture.

Stop winging it and start winning.

The EntreLeadership System is the small-business road map that takes the guesswork out of growing your business. To get the most out the system, download the easy-to-follow Getting Started Guide. 

Get the Free Guide

Small-Business Challenge #3: Time Limitations

If you’re always exhausted when your head finally hits the pillow at night, but you’re not sure what you even accomplished that day, you probably have a time problem. Nobody wants to feel buried day after day in urgent tasks that don’t have a huge business impact. And burning the candle at both ends doing work you don’t even like (and maybe aren’t good at) just because you don’t trust others to do it is also a drag. Time problems—especially when they’re caused by delegation issues—rob you of opportunities to build momentum.

The good news is, time doesn’t have to be your enemy. When you manage it well, it’s a friend that allows you to dream big dreams and do big things. And when you take control of your time, you’ll have margin to build a life you love beyond work.

Small-Business Solution #3: Integrate the right systems into your day.

When you’re already scrambling to stay on top of your workload, it can be overwhelming to hear, “Add something else to your day.” But stick with us. These tips will save you time in the long run and prevent the headaches of fixing bad habits, poor communication and crappy time management later.

  • Focus on your top three priorities each day. When you keep a short list of must-do items, it’s easier to keep them front and center in between emergencies. Sometimes your top priorities will include urgent and important tasks, like getting payroll set for payday. But usually, it’s the not urgent but important tasks that move the business needle. An example of this is building in time to carefully define your mission, vision and values.
  • Delegate work. As you get to know your team members’ strengths, you’ll see who’s ready to take on new opportunities. The more you coach and train rising leaders so you can delegate work to them, the more you make room for your company to grow.
  • Schedule weekly staff meetings. Your goal here is to have a regular, set time to clearly communicate updates, celebrate team member wins, and highlight your mission, vision and values.
  • Establish Key Results Areas (KRAs). When every team member is clear on their role, they know what winning looks like. That empowers them to go for it and help the whole business win.
  • Incorporate team member weekly reports. These are one-page updates from every team member on their morale, stress level, workload, and weekly high and low. Weekly reports help your team feel seen and heard and allow you to show you care about your people.
  • Have regular one-on-one meetings. Every team member should report to a leader and meet with them every week or two. This helps build rapport and creates a safe place for the team member to share their highs and lows and get clarity on their work. You can also use the time to help your team members grow.
  • Prioritize strategic planning. Once a quarter, schedule at least half a day for you and your key leaders to plan your desired future. This is your time to reflect on your wins and losses and define what you want to tackle next together.

Small-Business Challenge #4: Isolation

You’ve probably heard the phrase, “It’s lonely at the top.” And that’s especially true for business owners. A whopping 6 in 10 say they’re lonely.2 Why so many? For one thing, being the top dog comes with a lot of pressure to keep all the plates spinning and morale high. It’s also hard for business owners to know who they can trust with vulnerable issues. Then finding time to connect with those people is even harder.

No wonder only 37% of small-business owners regularly connect with other small-business owners for accountability, advice and encouragement.3 So how do they solve most of their problems and make decisions? On their own.

But here’s the thing—no one’s meant to carry the weight of their business alone. That’s a recipe for tunnel vision, limited productivity and unhealthy work-life balance. You don’t have to do business alone.

Small-Business Solution #4: Build relationships.

When you build relationships with other business leaders, you open the door for fresh ideas, new ways of thinking and good ol’ friendship. Those are wins worth chasing! Strong professional relationships also provide a huge bank of business wisdom you can call on whenever you need it. Here are some of the easiest ways to make connections:

Your Trusted Small-Business Solution

You’d call us crazy if we told you to keep doing the same things over and over and expect different results. And you’d be right! That’s a recipe for frustration—and eventually failure—in business. So don’t do that. Instead, confront the challenges we’ve presented to finally break bad cycles. And lean on EntreLeadership Elite as your ultimate business-growth ally.

This digital platform provides the tools and support you need to tackle strategic planning, team-member development, and long-term growth with confidence. We’ve worked with thousands of business owners over a few decades to help them overcome their small-business challenges. Here’s what Elite will help you do too.

Work the EntreLeadership System faster.

Just like you can work Ramsey’s 7 Baby Steps on your own to get out of debt, you can work the EntreLeadership System solo to grow your business. But Elite gives you all the resources to move faster so you’re free to focus on other things you care about too. Elite gives you three main resources.

  • Team-empowering tools and templates to help you save time, communicate better, and support your team
  • Leadership training and coaching through on-demand courses and live sessions
  • Like-minded community with other small-business owners who’ll encourage you and keep you accountable

Become a leader others want to follow.

To help you fit learning into your busy day, Elite includes bite-size lessons on leadership skills like hiring, delegation and communication. Plus, you’ll have access to a huge library of leadership and business keynotes and trainings delivered by top-notch speakers.

When you sign up for the Executive Coaching level of Elite, you’ll work one-on-one with a coach trained to help you supercharge your leadership skills.

Get your time back.

Doesn’t that sound freaking amazing? Elite saves you time by helping you integrate the systems and practices you need most right into your daily routine. You’ll have what you need to create new rhythms, improve role clarity, create the company culture you want, and so much more.

Connect with like-minded business owners.

When you join Elite, you’ll instantly become part of a community of hundreds of other values-driven business owners and leaders on a mission to build great teams and businesses. Best of all, you’ll have friends and mentors who cheer you on and celebrate your wins with you. For extra accountability and deeper relationships, you can choose the Advisory Group option of Elite.

Finally, instead of banging your head against the same old wall, you’ve got real solutions to find a new path forward. It’s time to unlock your full potential and the vision of success that got you started in the first place.


Next Steps: Get stronger. Move faster.

Stop trying to overcome your small-business challenges on your own. Build a stronger business and level up faster with Elite. 

Want to learn more about the EntreLeadership System? See how it works and download your free Getting Started Guide.  

Join EntreLeadership Elite

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Ramsey Solutions

About the author


Ramsey Solutions has been committed to helping people regain control of their money, build wealth, grow their leadership skills, and enhance their lives through personal development since 1992. Millions of people have used our financial advice through 22 books (including 12 national bestsellers) published by Ramsey Press, as well as two syndicated radio shows and 10 podcasts, which have over 17 million weekly listeners. Learn More.

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