Overcoming Obstacles to Achieving Your Goals

Jump To: Recognize What's Standing in Your Way | Quick Scan Guide |Common Obstacles | Quick Reflection | Fear: The Main Obstacle | Simple Process to Overcome Fear | Time & Focus Obstacles | Success Lesson |Download eBook

Overcoming Obstacles to Achieving Your Goals – Recognize What’s in the Way

When you’re deeply committed to personal goal setting, it’s tempting to focus only on vision, strategy, and tools. Those matter. But leaders who consistently reach their goals do something more: they learn to see and remove obstacles to success.

What Are Obstacles to Achieving Your Goals?

Obstacles to achieving your goals are the fears, habits, beliefs, and practical constraints that block you from taking consistent action on what matters most.

They can be external - things like limited resources, a demanding schedule, or lack of support. But just as often, the biggest barriers to your goals are internal:

• Fear of failure or criticism
• Procrastination and avoidance
• “Never enough time” and constant distractions
• Lack of clarity about what you really want
• Doubting your ability to follow through

Obstacles are the things you see when you take your eyes off your goals. When you don’t have clear, compelling goals, all you can see are obstacles like fear, procrastination, and lack of time. That’s exactly why you must have big goals for your life.

The stronger and clearer your goals, the more willing you are to overcome barriers to your goals and do the work required to achieve them.

Quick-Scan Guide: If You’re Facing This Obstacle, Do This

Obstacle

Remedy

“I’m afraid of failing or being judged.”

Name one specific fear in writing, then take a tiny 24-hour action anyway (send the email, schedule the meeting, or share the goal with one trusted person). Use the “Simple Process for Overcoming Fear of Failure” below to shrink the risk.

“I keep procrastinating and avoiding the hard work.”

Choose one 15–30 minute task that moves your goal forward and do it first thing tomorrow. Turn off notifications, set a timer, and don’t check email or social media until that one action is complete.

“There’s never enough time for my goals.”

Block a non-negotiable 30-minute appointment on your calendar each weekday labeled “Move My #1 Goal Forward.” Treat this time like a meeting with your most important client – because it is.

“I’m not clear about what I really want.”

Take 20 minutes to write a clear, one-paragraph description of your goal. Include what you want to achieve, by when, and why it matters to you as a leader. Vague goals become clear when you put them into specific words.

“I doubt my ability to follow through.”

Pick one small commitment you can keep for the next 7 days (for example, 10 minutes of planning each morning). Track your progress on paper. Each day you follow through, you build the identity of a leader who keeps promises to yourself.

Use this guide whenever you feel stuck. A few focused minutes choosing the right remedy can save you weeks or months of spinning your wheels and will help you keep overcoming obstacles to achieving your goals one practical step at a time.

Common Obstacles to Achieving Your Goals (and How Leaders Respond)

The more you understand what is standing in the way of your goals, the more power you have to respond like a leader. Here are some of the most common obstacles leaders and solopreneurs face:

1. Fear of Failure and Criticism

You imagine what might go wrong, how bad you’ll feel if you fail, or what others will think if you try and don’t succeed. When you are convinced that you run a high risk of feeling pain, it’s easy to become paralyzed.

Practical Example: A Solopreneur Who Launched in Spite of Fear

One solopreneur we worked with had a clear goal: launch a new service for small business owners within 90 days. On paper, she had everything she needed – experience, a loyal audience, and a solid offer. But fear of failure kept her stuck. She worried, “What if nobody buys? What if I look foolish?”

Instead of waiting to feel fearless, she took one small, leader-like step: she shared her goal and rough idea with five trusted clients and asked for honest feedback. Their responses helped her refine the offer, and their encouragement gave her the confidence to set a launch date.

By focusing on one small, courageous action instead of the entire project, she began overcoming obstacles to achieving her goals. When launch day arrived, she didn’t feel perfect, but she felt prepared – and the offer sold out its first round.

2. Procrastination and Avoidance

You delay starting. You wait for the “perfect time.” You stay busy with lower‑priority tasks instead of facing the few actions that would truly move your goals forward. Eventually, the delay becomes its own obstacle.

3. “Never Enough Time”

Your day is full of meetings, emails, and urgent requests. By the end of the day, you’re exhausted, and your most important goals didn’t move at all. Time feels like an enemy instead of a tool.

4. Lack of Clarity

If you’re not clear about what you really want, it’s hard to make decisions, set priorities, or say “no” to distractions. Vague goals invite vague effort and vague results.

5. Self‑Doubt and Limiting Beliefs

Deep down, you may wonder if you truly deserve success, or whether you’re capable of leading at a higher level. These silent beliefs quietly sabotage your progress long before any external obstacle shows up.

Every goal you set will require you to face at least one of these obstacles. That’s not a sign you’re on the wrong path - it’s a sign you’re pursuing something that matters.

Quick Reflection: What’s in the Way of Your Goals Right Now?

Before you move on, pause and do a brief exercise. This simple reflection will help you identify the obstacles to achieving your goals that you need to address first.

Reflection Exercise: “What Is In The Way?”

1. Pick one important goal

Choose a goal that truly matters to you - something related to your leadership, business, health, or finances.

2. List the top 3 obstacles in your way

Include both external and internal obstacles. For example:

• “Fear of failing in front of my team”
• “Too many meetings and interruptions”
• “I keep doubting my ability to lead this project”

3. For each obstacle, write one small action

Next to each obstacle, write one action you could take in the next 7 days to reduce its power. Keep it small and specific.

4. Circle the one action you will do first.

Leaders don’t wait for perfect conditions. They choose one meaningful step and take it.

This simple exercise helps you move from feeling blocked to taking practical, action‑oriented steps toward overcoming obstacles to achieving your goals.

Overcome Your #1 Obstacle to Achieving Your Goals Checklist

You’ve identified what’s in the way of your goals. Now let’s get practical. Use this simple checklist to pinpoint your top obstacle and create a 7 to 14-day plan for overcoming obstacles to achieving your goals. You can complete this right on the page in your journal or notebook.

Step 1: Identify Your Top Obstacle

Answer these questions in writing:

Question 1:  What is the one goal that would make the biggest positive difference in your life or business over the next 6–12 months? 

Question 2:  When you think about this goal, what is the first obstacle that comes to mind? 

• Is it fear (of failure, criticism, or success)? 
• Procrastination or lack of follow-through? 
• “Never enough time” or constant interruptions? 
• Lack of clarity about the goal or the next step? 
• Self-doubt or negative beliefs about yourself? 

Question 3:  How does this obstacle usually show up in your day-to-day actions?

Question 4:  On a scale of 1–10, how strongly does this obstacle block your progress right now?

Question 5:  What would be possible if you reduced the power of this obstacle by just 20–30% over the next month?

Step 2: Choose the Right Strategy for Your Obstacle

Based on your answers above, follow the path that matches your main obstacle:

If your top obstacle is FEAR:

• Revisit the “A Simple Process for Overcoming Fear of Failure” below.
• Today, complete steps 1–3: name the fear, challenge the story, and shrink the risk.
• Commit to one tiny 24-hour action that proves you can move forward in spite of fear.

If your top obstacle is PROCRASTINATION:

• Choose one goal-related task that you’ve been putting off.
• Break it into a 15–30 minute first action (for example, outlining a proposal instead of writing the full document).
• Schedule this action for the very start of your day tomorrow, before email, meetings, or social media.

If your top obstacle is “NEVER ENOUGH TIME”:

• Review the “Time and Focus” section below.
• Track where your time actually goes for 2–3 days (no judgment, just data).
• Block one recurring 30-minute appointment each weekday labeled “Move My #1 Goal Forward” and protect it like you would an important client meeting.

If your top obstacle is LACK OF CLARITY:

• Write a one-paragraph description of your goal: what you want, why it matters, and when you will achieve it.
• Then list 3–5 possible first steps. Choose the easiest, most obvious step and schedule it within the next 48 hours.

If your top obstacle is SELF-DOUBT:

• Write down the specific belief that is holding you back (for example, “I’m not ready to lead at this level”).
• Ask: “Is this always true? What evidence do I have that I can grow into this goal?”
• Choose one small action that demonstrates belief in your future (such as registering for a course, asking for mentorship, or sharing your goal with a supportive person).

Step 3: Create a 7–14 Day Action Plan

Now turn your insight into a short, focused action plan:

1. For the next 7–14 days, what is the ONE daily action you will take to reduce the power of this obstacle?
2. When exactly will you do this action each day? (time and place)
3. How will you track your progress? (checklist, journal, calendar, app)
4. Who will you share your commitment with for accountability?
5. What small reward will you give yourself when you complete the full 7–14 days?

Keep this checklist where you can see it – on your desk, in your journal, or on your phone. Each time you follow through, you’re not just completing a task; you’re building the identity of a leader who is committed to overcoming obstacles to achieving your goals.

If you’d like extra support as you work your plan, be sure to download the free Goal Setting for Success eBook below and subscribe to our free Leadership Tools newsletter. You’ll receive tools, reminders, and encouragement to help you stay on track.

Fear: The Main Obstacle That Stops Most Goals

For many leaders, fear is the number one obstacle to achieving goals. Fear of failure. Fear of looking foolish. Fear of success and the expectations that come with it.

Fear may feel overwhelming, but once you shine a light on it, you can start overcoming obstacles to achieving your goals one small step at a time.

Sometimes you aren’t even aware of the fear. You just notice that you “never seem to get around” to that important project, or that you always choose something safer and more familiar.

When you allow fear to lead, you protect your comfort zone at the expense of your future. When you lead yourself well, you acknowledge your fear - and then you choose to move anyway.

Your success in overcoming obstacles to achieving your goals will have everything to do with your ability to face fear, feel it honestly, and still act in line with your values and priorities.

A Simple Process for Overcoming Fear of Failure

Use this simple process whenever you notice fear standing in the way of your goals:

1. Name the fear

Write down exactly what you’re afraid will happen if you pursue this goal. Be specific.

2. Challenge the story

Ask yourself: “How likely is this really? What evidence do I have?” Often, the fear story in your mind is much bigger than the reality.

3. Shrink the risk

Break your goal into one tiny action you could take in the next 24 hours. The smaller the step, the easier it is to act in spite of fear.

4. Ask for support

Share your small step with a trusted friend, mentor, or partner. Let someone else know what you intend to do and when.

5. Review what actually happened

After you take action, notice how the reality compared to what you feared. Most of the time, you’ll discover the obstacle was much smaller than you imagined.

In the next chapters of this Goal Setting for Success course, we go deeper into facing fear of failure and how to respond when things don’t go as planned. For now, remember: fear is real, but it doesn’t have to be the boss of your goals.

Time and Focus: Hidden Obstacles to Goal Achievement

Not all obstacles are dramatic. Some of the most dangerous barriers to your goals are quiet: a scattered mind and a calendar that’s full of everything except what matters most.

Lack of focus and poor time use may not feel as intense as fear, but they quietly block more goals than any single crisis ever will.

Remove Time and Focus Obstacles to Your Success

As a leader, you can begin to remove these obstacles to success by asking a few key questions:

• “Where is my time actually going each day?”
• “How much of my week is invested in my top 3 goals?”
• “What could I stop doing, delegate, or delay to create space for what matters most?”

Real-World Example: Protecting Time for a High-Impact Goal

Consider a frontline manager who wanted to improve team performance by creating a simple weekly coaching system. The goal was important, but every day was filled with urgent emails, meetings, and “fire drills.” Months passed, and nothing changed.

Finally, he treated the goal like any major commitment: he blocked 45 minutes every Tuesday and Thursday morning as “Team Coaching Planning” on his calendar. He informed his assistant and his team that this time was not available for routine meetings.

By defending just 90 minutes a week, he created space to design a simple coaching agenda, schedule regular 1:1s, and track progress. Within a quarter, team performance improved – not because he found more hours in the week, but because he removed quiet time and focus obstacles that had been standing in the way of his goals.

When you consistently protect even a small block of time, you turn “never enough time” from an excuse into an opportunity for real progress.

You’ll explore “never enough time” in more detail in a later chapter of this course. For now, commit to one small change that protects focused time for your most important goals - even if it’s just 30 minutes a day.

"The ability to concentrate and to use your time well is everything if you want to succeed in business - or almost anywhere else for that matter."

- Lee Iacocca

Success Lesson #10 – You Can, But Will You Move What’s in the Way?

Every meaningful goal demands a price: your time, attention, discipline, and willingness to change. Many people can achieve their goals in theory - they have the talent, intelligence, and resources — but they never quite decide that they will.

A Story of Turning Obstacles into Opportunity

Imagine a leader who, from an early age, faced what seemed like impossible obstacles - physical limitations, limited resources, and constant reminders of what he “would never be able to do.”

Instead of accepting these obstacles as final, he chose to believe that his future was bigger than his present limitations. He worked, studied, and persisted. Over time, he not only overcame many of the barriers that held him back, he also used his story to inspire and help others do the same.

The details of your story will be different, but the principle is the same:

• You can have goals.
• You can see what is standing in the way of your goals.
• You can decide to move, one step at a time, through and around those obstacles.

Case Study: From “Stuck” to Steady Progress in a One-Person Business

A one-person consulting business had a clear revenue goal for the year, but after six months, progress was slow. The owner felt discouraged and overwhelmed. When she finally took time to reflect, she realized that three obstacles were in her way:

• Fear of reaching out to past clients
• A cluttered offer that confused prospects
• No consistent time blocked for marketing

Instead of trying to fix everything at once, she chose one new response for each obstacle:

• She made a list of ten former clients and reached out to just two each week.
• She simplified her offer into one clear “starter package.”
• She blocked 30 minutes a day for focused marketing tasks.

Within 60 days, she landed three new projects and felt back in control of her business. She didn’t eliminate every obstacle overnight, but she consistently chose new responses.

This is the heart of overcoming obstacles to achieving your goals as a leader or solopreneur: see what’s in the way, choose your next response, and keep moving.

The question is not “Can you?” The question is “Will you?”

Apply the Lesson – From Obstacle to Action

Try this simple exercise in your journal or notebook:

1. Draw two columns and label them “Obstacle” and “New Response.”
2. In the first column, list the obstacles that are blocking one of your key goals.
3. In the second column, write the new response you choose as a leader.

Examples:

Obstacle: “Fear of failing in front of my team.”
New Response: “I will share the goal with my team, ask for their input, and be honest about the learning curve.”

Obstacle: “Never enough time to work on my business.”
New Response: “I will block 30 minutes each morning for strategic work - non‑negotiable.”

The moment you choose a new response, you begin overcoming obstacles to achieving your goals and leading yourself more effectively.