Three Ways to Turn Obstacles into Gifts

Part 3 of the groundbreaking series on The Storytelling Matrix: a subtle field of energy at the heart of all business matters. You may also enjoy the first post in the series, Problem and Paradox, or the second, The Power of Personal Disclosure.

Obstacles suck. They are what you try to avoid or work around. Obstacles are where the flow of things gets bottled up; where things break down, or where you feel most out of alignment. Yet they play an important role in the progression of any story.

What are you trying to create in the world? Are you are a change agent, the leader of an organization, an entrepreneur? In nearly every organization or business, the language and experience of obstacles is playing out, no matter how carefully you plan, who you hire, or what you’re selling.

Obstacles are Critical to the Hero’s Journey

Your first response to obstacles is often to demonize them.

The language we use is often militaristic (e.g. attack that problem, conquer the challenge). It’s easy to have negative emotion toward what’s going wrong. So much so that it makes you want to avoid dealing with it. Often times, people know the bottleneck, constraint, or problem is there but no one wants to deal with it. Obstacles then turn into gremlins who’ve been fed after midnight.

Despite the furry devils, obstacles can be a tremendous gift on your path. You can’t discover, reveal, or embrace the full nature of your character without them. In fact, obstacles are the places where character is forged and revealed; they offer the perfect opportunities for you and your business to grow and become better aligned and more smoothly flowing. When you can embrace your obstacles, you invite the process of growth and transformation.

Sometimes the sheer number of obstacles you face can seem overwhelming, to the point of obscuring the path forward. Which ones really matter? How do you choose which obstacles to face and which ones to ignore? These are difficult choices.

Here are three strategies to consider. The sooner you begin to see your obstacles as a gift that will help you move forward, the sooner you’ll graduate the next level of your game.

1. Embrace the Discomfort

Transformation in any story comes from stepping out of your comfort zone. Imagine if Frodo never left the Shire. Or if King George of Britain never confronted his stutter. In hero’s journey terms, the protagonist at first often ignores the call to adventure. Yet eventually you reach a point where you must leave the place of comfort and step out into the wilderness.

Rarely do we opt into a place of discomfort. We have to be nudged there by either yearning or frustration. Typically we wince away from something that hurts, but the first step in seeing obstacles as a gift is to lean into the discomfort. In storytelling terms, you want heat. Look for the heat. The best stories emerge out of the smoking cauldron of creative tension.

The key to look for is “emotional overhead.” What are issues, subjects, or topics that are hard for you to discuss? What’s considered taboo or off-limits within your organization? What are the biggest areas of frustration or bottleneck? Those are the smoke signals for you to pay attention to.

You can’t be afraid to get close to this fire. Accept the fact that you will likely get burned. Pain is in fact a powerful motivator for change. You need to feel a little burn. In fact, when you reach the point of burning desire, there’s no fire that can stand in your way.

When you can say “This is important,” you’re actually saying yes to the obstacle. Everything starts to self-organize once you start to elevate something in importance. Just remember, it’s a gift calling you to step forward in a bigger way. Without it, you’d have no puzzle to solve.

You have to want it. Or least surrender to the reality that it must be faced. You must walk through the fire. Gold is often waiting for you on the other side. Your greatest source of untapped power is in the parts of your story that remain unreconciled.

2. Create Bounded Containment

It’s natural to want more freedom, options and choices. In particular, creatives and entrepreneurs love the feeling of open possibility. We live for it! Most of our decisions are biased towards freedom and flow and away from constraints and protocols. Which is why it’s so easy to avoid the difficult stuff.

Even if you’re on a path of freedom, your transformational story needs structure. Just as every canvas has an edge and every map needs a border. You want a boundary to work within and push against. Without a border you can’t focus or harness your full energy. You need a container.

That’s why it’s always easier for people to respond when you present them with a straw-model plan or a beta product. Not vague ruminations or vaporware. You’ve taken the world of abstract possibilities, and you’ve reduced it to something specific. You made choices about what matters most and it’s reflected in how you organize your story. This choice-making is key to the storytelling process.

Obstacles force you to delineate new boundaries and behaviors. They introduce a natural constraint that you must face or ignore at your peril. This demands that you to create structure! Obstacles are the alchemical fire that will help you make the difficult choices. In the best of circumstances, you feel you have no choice but to respond. It’s the ultimate motivational kick in the pants.

3. Find Mentors and Allies

It’s impossible to solve most major obstacles all by yourself. That’s why you need mentors and allies to help you walk through the fire. The very notion of an obstacle implies something out of your sight and awareness. You can’t see it clearly. You didn’t see it coming. You don’t know what to do about it.

By definition, an obstacle lives outside your sphere of understanding. That’s why you want to find your Yoda, your Dumbledore, or even just a gym partner. They’ll introduce a fresh perspective and added support, often without the emotional attachments that you bring to the conversation. Remember that your emotions are often what are blurring your vision and ability to confront the obstacle.

As you begin to tackle your problems you may discover an entire constellation of mentors and allies who can help you down the path. Commit to studying the subject you need to solve. Then you’ll start to see who you want to model yourself after, who you resonate with, and the mentors will begin to show themselves to you. The old wisdom is true: When the student is ready, the teacher will appear.

Finding your mentors or teachers doesn’t mean you won’t be working hard and making your own decisions. In fact, the most important thing you cultivate on the hero’s journey is self-knowledge. That’s the difference between a mentor and a false prophet — one strengthens your self-confidence, the other reinforces their own status and power. A false prophet will dictate to you what the answer should be. A mentor will help you see your options more clearly and empower you to make a more considered and conscious decision.

Seeing the Obstacle as a Gift from the Universe

Obstacles can be our greatest opportunities for character development and business transformation. Often it seems the universe conspires to create a challenging environment, a set of constraints that call on our core essence, our higher purpose, our innate strengths to propel us and our organizations towards a greater destiny.

From a personal health crisis, financial turmoil, losing relevance with your customer base, or questions about who you are as a brand, you’re facing your shadow. The obstacles you confront are just antagonistic characters playing their part in the story. They’re there working in service to you, advancing the plot, and supporting your transformation. It’s all in how you look at it.

How Do You Confront Your Obstacles? Share Your Voice.

Learning to see your obstacles as a gift is a path forward through even the most challenging of situations. Tell us how you confront the obstacles in your story.

  • What are the biggest obstacles that you’re facing?
  • What carries the greatest emotional overhead for you?
  • How do you turn adversity into an ally?

Please add a comment or a question below.

15 thoughts on “Three Ways to Turn Obstacles into Gifts”

  1. This is beautiful Michael – thanks for sharing. As I read this I related it to my own experiences in practicing yoga for many years. I met a lot of big obstacles from Day One, but something within me compelled me to keep facing the pain, discomfort and seemingly-thwarted hopes. Seven years into my practice, my experiences are very similar to the narrative you tell here (e.g. facing my shadows/unconscious areas, the need for a “container”, the arrival of mentors, and the powerful benefits that flow from transformation – i.e. going beyond what’s been learned before to realise latent gifts and strengths). 

    In Indian mythology, Ganesha (the mischievous elephant with a sweet tooth who rides around on a mouse) is a deity associated with yoga. He’s also the “Lord of obstacles”. The story of Ganesha is that he removes obstacles but also places them in our path to test our commitment and to develop our character. The storytellers who brought Ganesha into being knew what they were talking about. 

    Now I’m also experiencing this in my work—and the beauty is that once we’ve experienced a deep transformation through one part of our life/work, future changes happen much more gracefully. Perhaps that’s because we’ve learned to know ourself better, trust ourself in the face of our fears and to stop standing in our own way.   

  2. Once again Michael you have hit it out of the park with this post. Absolutely spot on. Thanks for your insight. Yes obstacles are a challenge but when we can embrace them knowing that they are there for a reason then we can see them as opportunities. I am a firm believer that things happen for a reason and even the most insane obstacle or crisis has had to happen at that moment for some powerful reason. As someone who lives in Japan, I love the Japanese (and Chinese) meaning for ‘crisis’ which includes two characters – one for “danger” and the other for “opportunity”. If we look at a crisis or obstacle as opportunity then we are in the frame of mind to embrace it and learn from it. Easier said than done, but true nonetheless. 

    Hey, look forward to seeing you next week for the workshop in NYC.  I am in town visiting and signed up.  See you then.


    1. Thanks Peter! I’d love to hear how you see the evolving identity of Japanese culture in light of the struggles their economy has faced over the past decade plus. Excited to finally meet in person. 

  3. Smart, Michael.
    I keep telling myself that the recession is a crucible that is forcing us -collectively- to take a close look at our priorities. I have high hopes for some enduring societal change; primarily, re-prioritizing relationships and quality time over material possessions. From what I know, the Great Depression seemed to leave that mark on a generation.

    Personally and as an entrepreneur, I see the daily obstacles of self-employment as a constant crucible. The longer I stay in the game, the stronger I become for the rest of my working life. It’s hard, I hope I never forget that, but it’s easier reading posts like yours.

    Thank you.

  4. Beverley Glick

    Profound thanks, Michael, because your post landed in my inbox at exactly the right moment. I had been facing what seemed like a boulder on my path until I reframed it as a gift and started telling a different story. And then my intuition led me to the Zen proverb: “The obstacle is the path”. Now I have a completely different relationship with the boulder. It’s still there, but it has transformed from a problem to a pot of gold. You continue to inspire me. I hope you will visit London some time soon as I’d love to experience your energy in person.

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  7. Donald W Duncombe

    I have several obstacles. This is my second attempt at a vision that came to me to develop a Bahamian cultural center. The first failed because taxis and Road Traffic Officials conspired to ensure that the business failed. The cruise vessel companies’ representatives gave emails that didn’t go any where. On contacting one she said it was not what the company wanted nor were their guests interested in Bahamian culture when they came to Grand Bahama. I lost about $250K which was my life savings and investment support from family. This left me with no opportunity to be reengaged in the former industry I was in, $200K mortgage, $15K car loan and others. My sister help financed a smaller version but I was prevented from collecting my own guests in my car because I needed a private franchise license which the government has under a moratorium that only Cabinet can grant. I have yet to receive an answer from anyone in the Cabinet. The local schools have not supported either even after flyers were distributed to all using meager funds. Grum Ma’s House Cultural Center is on Facebook and and at a site I am developing. Without funding it is difficult to walk through this fire to the other side but As you say , I must embrace these challenges and by God’s grace walk through. I must say thank you because I am here trying to figure a way through and finding your post was as a result of one of the goggles that you do when you don’t know what else to do after you have done all you can. I pray. I struggle. I think. I pray some more. The I just don’t know sometimes. Thanks for allowing me to find a means just to embrace and let this all out.

    1. Donald, thank you for sharing your story with us. I love your passion and vision, and deeply empathize for your heartache and frustrations you’ve faced along the path. Hope that our content and resources can continue to help you find the “path of lease permission” in turning your vision into reality. Think Junkanoo, and the lessons there for reinvention, imagination, and just owning your bad ass story. 😉

  8. It is a good read. I enjoyed it. Obstacles. Wanted to live on ocean for years. Tried everything under the sun. So many lessons. Then 15 months ago I said thats enough I’m not leaving this apartment unless I walk directly to it.

    A lot of transformations in me. Was supposed to get settlement and it has been delayed by months! When it was supposed to be a week. Brother.

    Cant leave unless it comes and obstacle gone. Yes I am still looking other ways. Lost my mind a few times in these obstacles.

    Just got to trust god will bring the message at the right time. I dont know but it seems every great person had the obstacle for years. Maybe God does it to develop character?

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