⛰️ Overcoming Fear, Processing Failure, and Why Having a Plan B Holds You Back

published6 months ago
10 min read

When I started All The Hacks two years ago, I had a dream that it would be my full-time job, but it wasn’t until recently that I committed to it. If you have an ambitious idea but are hesitant to commit, this post is for you. I recently interviewed Matt Higgins (🎧Ep 105) about his amazing book Burn The Boats, a framework to stop hedging and unlock your full potential. The conversation was so good that I knew I had to turn it into an actionable guide.

By the end of this post, you will have learned how to:

  • Uncover fear to build self-awareness
  • Unlock your motivations to discover your potential
  • Stress-test your ideas to avoid cognitive bias
  • Assess risk to solidify your plan A
  • Address failures to make sure you don’t quit

These frameworks will help you go all-in on your Plan A and finally burn the boats.

If you like this post, please consider sharing it with a friend, colleague, or family member that might learn from it. 🙏🏼 Thank you!

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📢 Quick Announcement

I'm also excited to announce that during my recording with Matt, I was convinced to finally launch the All The Hacks membership I’d been considering for a few months. I’ll share more at the end of this email, but I’m really looking forward to building it into a world-class program for all of you.

🚢 What does “burn the boats” mean?

Burning the boats originates from military strategy (and referenced in Sun Tzu’s The Art of War). The boat serves as a means of escape during battle. Therefore, burning the boats means cutting off the escape route, leaving only one path forward.

In modern times, this phrase refers to eliminating the obstacles that hold us back from starting something new or great. It’s a framework to ditch plan B and go all in on plan A.

For most people, the boats represent internal forces. To burn them, you must do the self-work.

The process of self-work is designed to reach deep, so this post will help make it easy for you to stay focused and clear.

Each section follows an order, beginning with the foundational questions. Some of you may have thought through certain questions, so you may start further down the framework.

To go even deeper, I recommend you check out Matt’s book, Burn the Boats.

◀️ Look Backward to Change Behavior

Uncover Fear and Build Self-Awareness

The first step towards unlocking your full potential is to look backward.

While self-awareness is a term used frequently, many resist the practice of reflection and assessment since it requires a level of vulnerability we are not used to. If you resist, start by thinking about the fear question:

“What am I afraid to [find out about myself]?”

We might fear truly understanding the deepest parts of ourselves for various reasons. Typically this resistance stems from fear of judgment from an authority figure, spouse, relatives, or friends or the stigma it creates. You weren’t born with this resistance; it develops from social and personal pressures.

Only once you understand the fear question and lean into the vulnerability can you ask:

“What’s holding me back?”

The purpose is to understand the obstacles and your relationships with them.

  • Are they physical or emotional?
  • Are they based on present or historical experiences?

Use Self-Awareness to Change Behavior

Once you’ve identified fears and isolated obstacles, you can change the behaviors preventing you from where you need to go. It’s easy to overlook the true nature of your behaviors in our day-to-day routines. This is why it’s important to observe and deconstruct our behaviors.

To do so, audit your thought patterns, motives, and behaviors by assessing the following:

  • “Why am I doing this?”
  • “Why am I acting like this?”
  • “Why did I do X?”

Your past behavior can only be resolved by looking at it with humility and facing it. If you do this, you’ll often realize you fooled yourself into believing these behaviors were helpful. Moreover, you have the mental strength to correct the behaviors.

Look Backward TL;DR

Tackle three obstacles to establishing self-awareness.

  1. Determine fear —> “What am I afraid to [find out about myself]?”
  2. Assess obstacles —> “What’s holding me back?”
  3. Audit behaviors —> “Why am I doing this?”

▶️ Look Forward to Discover Motivations

Look at Who, Not What

The second step towards unlocking your full potential is to look forward.

Some people might find themselves here right at the beginning. They already know what’s holding them back but don’t know what to do with it. And it stems from asking the wrong question.

Don’t ask, “what do I want to do?” (e.g., be a lawyer, doctor, etc.), instead ask:

  • “Who do I want to be?”
  • “How do I want to spend my time?”
  • “What environment do I thrive in?”

Reframe the questions to focus on context, environment, and the cues that tell you more about yourself than what you want to do. This process is about helping you identify who you are as a person.

Don’t Accept Your Idea; Stress Test It

According to Matt (🎧Ep 105), most people fail at the idea stage because they do not ask themselves the right questions at the outset. Typically, when an idea surfaces, people are too quick to call it valuable and find a way to implement it. This puts you at risk.

Simply having an idea doesn’t make it a good idea. You must scrutinize it and focus on opportunity cost to determine if this idea will sustain you long-term.

When you develop an idea project yourself three years and ask yourself the following questions:

  • Is this idea big enough?
  • Is it interesting enough?
  • Is it valuable enough?

This exercise eliminates a cognitive bias we all suffer from when making decisions. We default to comparing our current situation vs. our idea because we are so desperately trying to escape our current situation.

Instead, we should assess that idea vs. our imagined situation three years from now. We can use it to determine whether we are “running to or away from something.” And you want to be running towards something.

The process of pressure testing our ideas aid in more sustainable decisions.

Look Forward TL;DR

Tackle two hurdles to identify motivations.

  1. Determine who, not what → “Who do I want to be?”
  2. Stress test ideas → “Is this idea big, interesting, and valuable enough to sustain me?

🅰️ Go All-in on Your Plan A

We’ve looked backward and forward and stress-tested our idea, so now we want to turn that idea into action.

What happens next is you get stuck.

Why? Risk and fear.

Getting unstuck and building a plan A requires synthesizing that risk and fear. Those who can fully commit have done the work at the forefront.

We will face external and internal doubts whenever we undertake a challenging endeavor that takes a long time. If you have gone through the synthesis process, you can draw on the memory and the clarity to overcome these doubts. If you haven’t done so, your doubts will prevent you from committing.

You can use this risk exercise to solidify your plan A:

  1. What’s the worst possible thing (that could happen) if this does not work out?
  2. What would I do if the worst thing happened (and how would I mitigate it)?
  3. What’s the probability of the worst-case scenario materializing?
  4. What would I be willing to endure for a Plan A workout?

You decide when it becomes a plan A.

🅱️ Plan B

When people think about Plan B, it’s in the context of “if Plan A doesn’t work out, what other options do I have?”

That’s a risk mitigation question.

But it should be clear by now that if you went through the Plan A risk exercise (above), you’ve already incorporated risk mitigation. That means Plan B is not about de-risking but achieving Plan A’s subordinate goals.

Wharton Business School found that mere consideration of a Plan B is enough to prevent you from achieving Plan A.

I’ll illustrate plan B using the same example from the podcast:

I want to be a musician.

Bob’s Record Store is the subordinate goal. Getting a job in music is very different from being a musician. Plan B is a way to relieve the pain and discomfort that comes with pursuing your true goal.

🤔 Having a Plan B vs. Knowing a Plan B Exists?

Some people are inherently thinking about all the possible scenarios and options to put themselves in the best position (…raises hand slowly 🙋‍♂️).

But there is a difference between knowing a plan B exists vs. planning for one.

Let’s look at some of the nuances with our musician friend again:

  • Pre-planning your escape route to Bob’s Record Store differs from knowing you could find a job somewhere “even if everything went wrong.”

The former is a plan B; the latter is not.

  • Suppose you have a conversation with a friend about wanting to be a musician. And during that conversation, they plant in your mind “even if everything went wrong,” you could work at Bob’s Record Store.

Just because you heard the concept of a plan B doesn’t make it a plan B. The key is in the sequencing. If you had gone to a friend before doing your risk synthesis exercise, then yes, you’ve likely opened yourself up to internalizing a plan B (and the doubt that comes with it).

But if you’ve gone through the framework and exercises, committed to your Plan A, then talked to a friend, it’s more likely their doubts will go in one ear and out the other.

You can’t have a plan B until you’ve established a plan A.

🤕 When Things Don’t Go Right…

Along the way, things will go wrong.

  • You wanted to be a musician.
  • You decided to go all in.
  • You do your first gig; no one shows up.

Processing failures are one of the main reasons Matt wrote Burn The Boats. His assessment of the most successful people shows that persistence is the most powerful predictor of success. As long as you keep going, you will succeed.

When things don’t go right, they expand their definition of success to accommodate setbacks. As a result, they redefine success differently. This is why processing failure correctly will help maintain persistence.

Here’s Matt’s framework addressing failures and missteps:

  1. Accept that the goal is to continue (to survive)
  2. Acknowledge the failure
  3. Don’t let that failure penetrate your identity
  4. Extract the value from that failure, iterate, and implement the change
  5. Never look at that failure again

Think of it this way: when the musician fails to be the lead guitarist, they find a way to be in the band.

Plan A is not the delusional belief that you will get what you are entitled to; instead, it’s the utter commitment to the goal and decision frameworks you have installed. You should always course correct when necessary (with plan A in mind).

🥪 The Best Ideas are Gut Sandwiches

Many of you will find your Plan A to be emerging ideas. When you are at the forefront of innovation, it can be lonely. There is an inverse relationship between the potential upside of an opportunity and the amount of supporting data. And don’t expect your friends or family to be able to see it the way you do.

The lack of supporting data is an indicator to keep going.

Matt’s advice: opportunity arrives before the tipping point of evidence. So look for pragmatic optimists who can help you cradle and shepherd your idea without needing the data to prove it true. It’s important to trust your instincts and intuition.

With that in mind, I told you I committed to my Plan A this year with All The Hacks, so I have something new to unfold.

📒 Workbook Exercise

I got an amazing email from Ligaya at Malaya Publishing who specializes in turning content like these newsletters into short workbook activities for readers to apply the lessons to their own lives. I wanted to share the one she made for this post, so please check it out and let me know what you think.

🙋 Join the All the Hacks Membership

During my interview with Matt, I was convinced to burn my own boat by launching an All the Hacks membership before everything was finalized. While it’s still early, my vision is to create a valuable membership with perks/benefits that more than makeup for any membership fee. Think AARP for a younger demographic that loves deals, travel, and experiences.

That said, I don’t have any of that built yet, so here’s what I’m going to commit to offering those who sign up now:

  • Monthly members-only video calls
  • Ability to share ideas for upcoming interviews and podcasts
  • My eternal gratitude for your support of me and All the Hacks
  • All the future perks and benefits I'm working on 😊

So if you want to sign up and support me, you do that here:

That said, I know it can be annoying to feel pressured by so many creators to sign up for another membership, so please do not feel pressured to join. I truly hope I can deliver more value to you than it costs, but I never want anyone to feel pressured to join.

💭 Final Thoughts

If you have gone all in on your Plan A (or strongly considering it), please tell me about it. Since doing this myself, I know exactly what you’re going through!

I hope this post was helpful, but if not, please reply and let me know what you’d like to see more of in the future.



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