
There are so many things that stop us from living the life of our dreams, but are you expecting challenges on your journey? When we expect obstacles, foreseeing them – we do a better job of ensuring success and completion!
I’m not talking about the obstacles of waiting for the right time or needing to feel ready. I invite you to consider actual obstacles that you encounter once you allow yourself to dream and plan. Things like not making your goal a priority and failing to schedule enough time to work on it. Or failing to commit and have accountability for the duration of the project.
Most of us plan out the dream, without actually considering the problems and obstacles that we will encounter. I’m not talking about over-thinking and catastrophizing! But rather, rational and logical planning and visioning. Taking a long view which includes possible hurdles.
Finagle’s Law suggests:
Anything that can go wrong, will go wrong, at the worst possible time.
There is no reason to be blindsided, failing to anticipate hard times.
Expect obstacles and foresee the challenges
If you have ever done any canoeing, kayaking or white water rafting, you have experienced the expectation of getting from the calm water into white water. Depending on how adventurous you are, you expect that there will be drops, rocks and even potential to get dumped into the water!
But the truth is that, before you even hop into the river, you already have mapped out a course. Where will you get into the river? At what point, will you find the white water and have to navigate through it? And finally, where will you pull your kayak or canoe out of the river again?
When you go white-water rafting or kayaking, you expect obstacles, you foresee the challenges that lie ahead, and you plan for them. Depending on your level of expertise and your adventurous heart, you might even train for it.
When you are planning your life goals and dreams, expecting obstacles and challenges along the way should be part of your preparation.
Obstacles you can foresee & plan for:
There are many obstacles that you can foresee and plan for, including:
- scheduling – What time obstacles will you need to take into account? Where will you be challenged to make time? Which steps of the process require more time and commitment?
- underestimating the difficulty – Be realistic about how hard some of the stages will be so that you can plan and adapt accordingly. What skills might you need to learn before you reach higher levels of difficulty? What knowledge do you lack when you start that should be acquired along the way?
- lack of creativity – When you run out ideas, how will you get back into flow? Be aware that this happens, particularly at stressful times – who will you ask for help? Where will you find a source of creativity to spark ideas?
- you need to put in more effort – Let’s be realistic, there will be moments along the journey that what is required is simply more hard work. Know this. Plan for it. And recognise when that moment has arrived.
- vague aspirations, plans or goals – From the very outset, understand that if your plan, dream or goal is too vague, this will create challenges for you in the future. Clarify your vision and mission. Get clear on your purpose.
Before you even embark on your journey, take time to brainstorm all the possible obstacles that will arise. Make a timeline and identify when different obstacles may show up – and make notes for yourself about how you will face them.
Imagined obstacles and self-sabotage:
Perhaps the biggest enemy in your endeavour is your ability to self-sabotage.
Expect this.
Understand the ways that you sabotage yourself so that you can identify when you are doing it. If you feel you aren’t very good at identifying this for yourself, then consider having a coach, a mentor or simply an accountability partner.
Possible forms of self-sabotage include:
- seeing your mistakes as failures, rather than as results and learning opportunities;
- distractions or lack of focus;
- disorganisation or procrastination;
- overthinking, which may cause you to freeze or be paralysed;
- giving up before you’ve started to see results;
- fear of success;
- negative thoughts, which you dwell on regularly;
- lagging confidence, as you don’t see the results as quickly as you hope.
Consider the ways that you feel self-sabotage protects or safeguards you. There’s a deep, underlying reason anyone practises self-sabotage. Unless you identify the root causes, you will struggle to uproot it! These reasons might include – self-worth, undeserving or even the need to control everything.
Provide yourself with time and space for self-reflection – because with awareness comes the ability to change those habits. You can rewrite those neural pathways, simply by repeating new habits.
The reality of unforeseen challenges:
Sometimes, the hurdles are unanticipated. But you know better! Expect obstacles, prepare accordingly.
We’ve already had a look at the internal obstacles, but now let’s examine the following –
- social: people in our lives may react and respond in unexpected ways to our plans and goals. While they may care for you, they can be threatened by any change in the dynamic of your relationship. Perhaps they are unsupportive when you expected their support. Pay attention to those supporting you and notice who is holding you back. How can you change the dynamic?
- circumstances: consider whether the circumstances which have arisen are truly independent obstacles or whether they are results and feedback of your planning and efforts so far. What can these results tell you about your implementation?
Of course, some external obstacles are truly unexpected and beyond your control. For example, there could be an economic change, a natural disaster, or some type of physical limitation. But, before you simply jump in, consider what your game plan might be for facing this new challenge.
Your game plan for handling obstacles:
As you prepare and plan, also include a game plan for how you choose to handle the unexpected. Have an idea of ways to approach obstacles, even though you don’t know what those obstacles are.
For example, consider questions such as:
- Who will I call when I am stuck?
- What resources have I identified that might help me find an answer?
- What type of response do I want to have when I encounter a problem?
- How will I make time for handling unexpected obstacles?
- When will I revisit my plan and goals, to notice when I have gotten off track because of obstacles?
- How will I approach difficult conversations when my relationships change?
Overcoming & Leveraging your Challenges
There will be obstacles, there will be doubters, there will be mistakes.
-Michael Phelps-
When you understand that obstacles are great for your learning and growth, you’ll find your strengths! Use the challenge of new obstacles to clarify your goals, plans and the next steps to take.
This will often mean using your schedule wisely, prioritise what is truly important, not simply what is urgent. Know that you will learn new skills, and it will often be hard and stretch you beyond what you thought you could handle. But if you put in the work, you will reap the rewards!
The first step, no matter what the challenge or obstacle, is to approach your self-reflection with compassion – for yourself and for others. You already know to expect obstacles. So, in spite of the situation, allow yourself to return to the desire that fuels the dream. What is your end game? How do you want to express compassion – for yourself or for others – in spite of the internal or external challenges you are facing?
When you consider all that is available to you through the experience, give yourself the opportunity to not only use your head but be guided by your heart and gut! Trust that you have all the inner wisdom that you need.

Life is about overcoming challenges. If not for understanding them and challenging yourself to overcome them life wouldn’t be worth living
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