How To Fail Smart: Your 3-Step Guide to Prudent Failure

Discover the power of "Prudent Failure", intelligent experiments and after-action reviews for rapid personal and professional growth, and how to turn failure into your secret weapon.

Today, I am going to show you how to transform failure from something to be feared into a valuable source of insight, creativity, and growth.

Most people dread failure, which keeps them from taking action altogether. However, inaction leads to stagnation and, ultimately, failure.

This is a paradox. People are afraid to take action to avoid failure, and eventually, they will fail. This is a fundamentally flawed mindset.

I am going to guide you through a process for clearly understanding and acknowledging failure so you can leverage it to drive personal and professional growth.

Just as the fire purifies gold, failure refines your character and ideas, making you stronger and more resilient.

But what kind of failure? Is every failure the same? Failure is multi-dimensional and context-dependent. One person's perception of failure may differ entirely from another's. Context plays a crucial role, as does the root cause of failure. Why people fail indicates the lessons to be learned and the next steps to be made.

Most people try to avoid failure entirely to avoid the discomfort it's usually associated with. That's fundamentally wrong because failure shapes your ability to learn and grow.

Instead of dreading it, you must create an environment (internal -inside your head- and external) where failure is acknowledged, categorised and processed appropriately, and mined for its learning potential.

Let's start with the 3 main questions you need to ask yourself whenever you experience a failure (or what you believe is a failure).

3 critical questions

To correctly identify the root cause of failure, ask yourself these questions and try to go deeper by expanding on your answers with a few more "Whys".

  1. Why did I fail? Was it because of something I did or something I didn't do?

  2. Did I fail because of unforeseen circumstances or other external factors I could not have predicted or prevented?

  3. Did I fail because I ran an experiment that didn't work out?

Your responses matter.

If you fail because of your wrongdoings or inaction, you can learn from that failure and do better next time. It's a matter of skills or execution.

If failure occurs due to unforeseen circumstances, you cannot do much about it, but you can use your observation skills to identify hidden patterns or gain insights that may prevent the same failure from happening again.

If you fail because you want to test something, bingo! That's the best kind of failure that can happen to you. It's the result of intelligent experiments.

In the first case, failure could have been prevented or avoided. In the second case, not. In the last case of intelligent experiments, failure is expected or anticipated because that's when learning takes place.

Most people see failure as something that happens or does not happen. The reality is far from it.

Take another look at the cases I mentioned above. Did failure just happen? Randomly? Or was there a cause-and-effect relationship?

If we look deeper, we can see that failure is random. Therefore, it can be managed.

If you build on your skills, learn new ones, learn from past wrongdoings, and take proper action, you minimise the chances of failure.

If you zoom out and observe your external environment, looking for trends or hidden patterns, you can anticipate and better prepare for circumstances that are not ideal. You can't eliminate the risk of failure (because you can't control everything), but you can decrease it and be more ready to mitigate its consequences.

If you plan thoughtful experiments to test new assumptions, ideas, concepts, and systems, you will only win because you either improve your life or work or learn from the insights in case of failure.

Failure is about agency. It will happen more frequently and more intensely if you have low agency. If you have high agency, you can predict, anticipate, find solutions, take proactive action, and shape your future. No one can do that 100%, but 75%, even 50%, is much better than 1% or 0% (no agency).

From a haphazard to a prudent approach to failure - A significant mindset shift

Most people take a haphazard approach to failure, ensuring it occurs repeatedly, with greater intensity and more difficult-to-mitigate consequences.

This approach is random, disorganised, and unplanned, without careful thought or strategy.

Their actions and behaviours lack direction, consistency, or preparation.

They often make choices and decisions without considering the long-term consequences.

And they certainly don't have clear goals or a concrete plan to achieve them.

Here are a few examples of approaching failure haphazardly.

If someone spends money impulsively without budgeting or considering future financial needs, they find themselves struggling financially when unexpected circumstances arise. They call it bad luck or blame the economy or the market.

If a person neglects their personal relationships (with family or friends) and interacts sporadically without much effort or thought, they weaken over time due to a lack of trust and connection. They say, "We just drifted apart" or "I was too busy". No wonder those broken relationships struggle to repair, and people fail to receive much-needed support from those they essentially cut ties with.

If someone completes tasks or projects at work without prioritisation or adhering to deadlines, their performance appears erratic, leading to missed deliverables and strained relationships. Solopreneurs struggling with their productivity often experience this kind of haphazard failure, wondering what went wrong each time and getting disappointed (some to the extent of quitting their projects or business altogether).

I have also observed otherwise talented professionals face career stagnation and dissatisfaction because they jump between jobs without having clear goals and building the right skillset.

This haphazard approach to failure leads to constant setbacks (and more failure).

A lack of proper action, mindless action (without much thought and effort), and reactive behaviour (instead of proactive) create a heavy mental and psychological burden: overwhelm, negative emotions, stress, anxiety, and burnout.

Furthermore, opportunities are constantly missed, and the overall trajectory of life and work takes a downturn, limiting personal and professional growth.

The answer to haphazardness when approaching and managing failure is prudence.

Opting for Prudent Failure

Where haphazardness leads to unnecessary risks and unpreparedness, prudence fosters control, forethought, and adaptability.

Taking a prudent approach to failure means being careful (but not risk-averse), wise, and practical in making decisions or taking actions, especially when considering the potential risk of failure and negative outcomes.

It's about exercising foresight, good judgment, and caution to minimise risks, learn from setbacks, make informed choices and decisions, and even plan for controlled failure.

Planning for failure as the outcome of a test or experiment is the best approach because that's where learning and growth happen.

Being prudent means thinking ahead, weighing your options carefully, and planning for potential challenges or opportunities. It doesn't mean avoiding risk entirely. It's about a healthy, thoughtful approach to risk.

Here are a few examples of a mindset shift from haphazardness to prudence.

Instead of spending all your earnings, you create a financial buffer for emergencies, invest another portion wisely, and avoid unnecessary debt. This way, you are always prepared for unexpected circumstances and avoid the trap of blame games.

A prudent approach to health involves taking care of it before medical emergencies occur. This includes eating a balanced diet, exercising regularly, taking care of your mental health, and scheduling medical check-ups to avoid preventable diseases.

When it comes to relationships, a prudent person communicates clearly and sets healthy boundaries to build trust and reduce the chance of misunderstandings or conflicts. It's not about them, it's always about you.

When working on an important project, prudence means considering possible risks, evaluating any opportunities coming your way, and creating contingency plans (for example, allocating more time for the project's critical tasks or preparing backup solutions).

When making career moves, you must evaluate the pros and cons of job opportunities and avoid acting impulsively (and then regretting your decisions). A career not synced with your wants and aspirations and not aligned with your values and priorities requires much time and energy to change (and it's a source of intense regret).

Adopting a prudent approach to failure does not mean eliminating failure entirely, but it equips you to handle failure constructively and plan for controlled failure for learning and growth purposes (See further below for more on Intelligent Experiments).

Mastering the Art of Prudent Failure in 3 steps

Prudence is a balanced approach to failure. It's not about risk aversion, overthinking, or (worse) inaction.

It's about taking deliberate action that ensures the best possible outcomes:

  • avoiding failure

  • making failure and its consequences less intense

  • gaining insights and learning

Here is how to master the Art of Prudent Failure. Note that the 3 steps below can be taken simultaneously. It's not a 3-step consequential process but a framework to help you build your prudence.

1. Conduct After-Action Reviews and build a Failure Portfolio

The first and most crucial step is to reflect on your failures and understand why they happened in the first place. Instead of dreading even the thought of failure or analysing it, sit with it. Take quiet time and reflect on what went wrong, without pressure but with self-compassion.

The goal is to create your personal Failure Portfolio. Just as an artist or a model makes a portfolio to showcase their best work, you create a portfolio with all your failures, whether small or big.

It serves as a tool for learning from mistakes and ensuring you improve your future decision-making and actions. It can show you what you can improve or change.

To start the process, ask yourself the following 4 questions first:

  • What did I expect? It's essential to define your goal or hypothesis clearly. What did you aim to achieve? What hypothesis did you want to test?

  • What happened? Describe the actual outcome in detail and identify the gap between expectation (goal or hypothesis) and reality. Be as honest and as objective as you can.

  • Why? Analyse the reasons behind the outcome to discover the root cause. This is the question to help you categorise your failure as planned (because of an experiment) or unplanned (avoidable or preventable, or not). This will help you identify skill gaps, external complexities, or flaws in the experiment itself.

  • What are the next steps? Based on the insights you gained, adjust your actions and behaviours accordingly. What skills should you build or improve? How can you better predict and anticipate external circumstances? Is there a way to improve the experiment's design?

After completing this reflection process, write everything down in your Failure Portfolio: the main ideas for each of the four questions above, plus the type of failure (planned or unplanned; if unplanned, avoidable, preventable or not).

Here are three examples (for each type of failure) to visualise it better.

  • Goal: deliver the project to the client before the deadline

    • Actual outcome: missed the deadline without asking for more time beforehand

    • Root cause: poor planning and procrastination

    • Type of failure: unplanned and preventable

    • Next steps: plan the workload, stick to the schedule, allow for an extra time buffer to accommodate any emergencies, and ask for more time if needed (it's essential to be clear on what you need and why)

  • Goal: launch a new service as a coach solopreneur

    • Actual outcome: the launch was derailed due to unexpected illness

    • Root cause: no buffer or contingency plan

    • Type of failure: unplanned and not preventable, BUT mitigable

    • Next steps: when planning for important projects or launches, allocate more time and build buffer zones to avoid derailment (launch cancelled or postponed), and create backup plans (for example, have someone available to step in and help, if needed)

  • Goal: test a new productivity plan for your work

    • Actual outcome: the new system failed to save you time and help you get more work done

    • Root cause: it was too tight and rigid, and led to stress and mild burnout

    • Type of failure: planned experiment

    • Next steps: repeat the experiment after refining it to be less rigid and allow for more rest between time- and energy-consuming tasks.

Creating your Failure Portfolio and regularly reviewing it can ensure you don't repeat the same mistakes that led to failure, and improve your decision-making and actions.

The goal is to achieve a balanced approach: not overly cautious (and risk-averse), not recklessly experimental (which may negatively impact you or your work).

One last thing. After creating the Portfolio and reviewing it periodically, you can level up your awareness by introducing the concept of predictability as well.

Prediction Calibration is a critical skill that helps you align your confidence in predictions with the actual outcomes. We often fail because we mispredict outcomes. For example, you want to launch a new online course and be 90% confident it will be a success (=achieving at least 1000 purchases) when, in reality, the launch was disappointing and only scored 100 purchases. Why was your original confidence not aligned with reality?

People sometimes get overly confident about the outcomes of their actions or plans. Analysing the discrepancies between prediction and reality can help you refine your predictions, learn from mistakes, improve future decision-making, and manage risk and uncertainty.

2. Prevent failure with the FMEA

To prevent future failure and mitigate its consequences, you must break down the task or project into its components and analyse each one thoroughly to identify potential failures and their impact on the task or project as a whole.

This technique is primarily used for technically complex situations and was heavily leveraged to anticipate problems in military systems. However, I have found that the Failure Mode and Effect Analysis (FMEA) can tremendously help with life, work, and business issues.

It's a proactive approach that examines:

  • Potential failure modes for each component

  • The effect of each potential failure on the rest of the system (or task or project)

  • The criticality of different failures

As a solopreneur (but not necessarily as such), you can adapt the FMEA method to prevent or avoid personal and professional failures.

Here are the steps to do it effectively:

  1. Define your focus. Identify an area in your life, work, or business, where failure could occur. For example. delivering projects on time, managing your finances or cash flow, meeting your clients' expectations, or maintaining a healthy work-life balance. You may also pick a specific project or task.

  2. List the potential failures. What can go wrong? Spend a few minutes brainstorming failure modes for each area, task or project. For example, late delivery of work due to poor time management and procrastination, or financial hiccups due to unexpected expenses or a dry period.

  3. Analyse the effects. Ask yourself "What would or could the impact of those failures be?". Be realistic and pragmatic. Don't overestimate and dramatise the consequences, but don't underestimate them either. For example, consistently poor delivery of work to clients could lead to customer dissatisfaction and lost deals. Or the financial roller-coaster could result in debt, missed opportunities, or even force you to close the business.

  4. Identify the root causes. Which factors could lead to those failures? Ask yourself "Why?" at least three times to dig deeper and discover the root causes. In our examples, procrastination due to perfectionism could be one of the reasons of late delivery of work. Or your lack of marketing and business development could slow down lead generation and new client acquisition, causing cash flow problems.

  5. Rank the risks. How severe each potential failure could be? How likely is each one to happen? Can you detect them early? These are three factors you should use to rank the risks. Then, prioritise those failures that can be severe, very likely to happen, and difficult to detect early. Focus on the most critical risks first.

  6. Get creative and find solutions. Plan and implement actions to address each high-priority risk. How can you prevent them from happening? Are there proactive ways to avoid them? For example, to prevent late delivery of work in the future, you can set realistic goals and deadlines, allocate enough time to complete them, create buffers to be used in case of unexpected circumstances, and communicate proactively. To prevent financial issues, focus on lead generation, upsell to existing clients, and create an emergency fund just in case.

  7. Monitor and review. Revisit your processes regularly and assess if they need to be further improved. Incorporate new learnings from recent failures to improve your solutions.

This is a continuous process, not an one-off one. This is why it's crucial to use feedback loops, where you can learn from mistakes and failures, feed the process with new learnings and insights, see how they work (or not), and make appropriate changes.

Neither the inputs or the outputs of the FMEA process are static and set in stone. They change as you or your life and business change, evolve and grow.

3. Anticipate and plan for Prudent Failure

Prudence allows for deliberate actions that are informed by foresight and practicality, ensuring the best possible outcomes while managing risks sensibly.

Now, let's see how you can implement those Prudent Failures. Others call them Intelligent Experiments. Whatever the name, the goal is the same: to foster a mindset of curiosity, innovation, and continuous learning, regardless of the outcome of the experiments.

It sounds cliche but you either succeed or learn. Failure is just a label we put on outcomes. This labelling carries a lot of emotional and psychological weight and this sometimes crash people.

Let's reverse that. Structured experiments are a relatively safe yet curious way to push your boundaries and level up, whether in life, work, or with your business.

You don't have to be a scientist to conduct such experiments. However, you must keep in mind that there are three conditions to be met for an experiment to be prudent:

  1. Hypothesis. You must state the hypothesis cleary before starting the experiment. This sets a specific standard against which you will measure the experiment's success at the end. For example, you may want to test a new productivity system by waking up at 5 a.m. and doing deep-focus work until 8 when the world wakes up. Or you may test a new sales approach to prospective clients.

  2. Frontier-pushing. For the experiment to yield new learning and register wins, it must be about something that lies beyond your comfort zone or business-as-usual. The hypothesis - task must push your boundaries so you can make leaps of growth if the test is successful. For example, you may want to start with public speaking, something you dreaded until now. Or if you are an introvert (like me), you may wan to test how selective networking at an event might go. You may spend a lot of energy and time (before, during and after) but there's a purpose.

  3. Contained impact. The last condition to be met is that the experiment's impact (in case of failure) is contained. Prudent failures are about experiments with calculated risks and a minimal to medium impact on you, or your work and business. There's no "intelligence" to be found if you conduct an experiment that ruins your business or destroy a relationship with a long-standing client. You can't experiment just for the sake of it. For example, you may want to focus on a new masterclass to build new skills and safeproof your business. That may require a lot of time and energy, and you may struggle with serving your customers. But overall it has a specific, limited impact. The same goes for when you want to invest money in what sounds like a luring opportunity. Instead of investing 50% of your savings, you may start with 10% and see how it goes.

These conditions also sync with the steps of the process.

When you decide to set a Prudent Failure in motion and conduct an Intelligent Experiment, you must first define your hypothesis, set the right boundaries (what it includes and how long you will run the experiment), carry it out, track progress closely, and evaluate the outcome at the end.

Ask yourself these questions:

  • Is the hypothesis verified or not?

  • Did your goals and expectations sync with reality or not?

  • If the experiment was successful, what new did you learn and how can you incorporate it into your way of doing things or business?

  • If the experiment failed, why did it fail? Was it the hypothesis or the design and execution?

Here are a few life, work, and business examples of Prudent Failures.

Life Example: Diving into a Plant-Based Diet

Imagine you're about to shake up your entire food game by going plant-based for 30 days. Your hypothesis? This radical shift will supercharge your energy levels and sort out your digestion without leaving you feeling isolated or nutrient-deprived.

Frontier-pushing: For a meat-lover, this is a bold move. You'll need to get creative with new recipes, keep an eye on your macros, and navigate those tricky social gatherings where everyone's asking, "Where's the beef?"

Contained impact: By limiting the experiment to just 30 days and pre-planning your meals and supplements, you're keeping the risks in check. If things don't go as planned, you can always revert to a modified diet that still gives you some of the benefits. Weekly check-ins will help you track how your body's responding. If it all falls apart, you'll still have some valuable insights to take away.

Work Example: Revolutionizing Your Workday with Deep Focus

Here's a challenge: what if you blocked off your calendar from 9 AM to 12 PM every day for some serious deep work? Your hypothesis? This will boost your productivity by a whopping 40% without alienating your team.

Frontier-pushing: This is a big ask if you're used to being reactive and meeting-driven. You'll need to assertively guard your time—a skill that's outside many people's comfort zones.

Contained impact: Run this experiment for two weeks, and make sure your team knows what's up. Track your progress closely—how many tasks are you knocking out, how many meetings are you rescheduling, and what's the feedback from your colleagues? If things don't quite work out, you can always adjust your approach without risking your career.

Business Example: Letting Go with Outsourced Content

As a solopreneur, it's tough to let go of the reins, but what if hiring a freelance writer could save you 10 hours a week while keeping your content top-notch? Your hypothesis? This move will free you up to focus on what really matters—growing your client base.

Frontier-pushing: For someone who's used to micromanaging, this is a leap of faith. You'll need to find a freelancer whose tone and research skills align with your brand.

Contained impact: Start small. Try it out for four weeks with just one blog post per week, and keep your budget in check. Track how much time you're saving, how your client growth is looking, and what your readers are saying. If it doesn't quite hit the mark, you can always adjust your strategy—maybe keep the freelancer for editing or research instead. That way, even if it doesn't work out as planned, you'll still come away with some valuable lessons.

Wrapping up

In conclusion, it's time to ditch the haphazard approach to failure that leaves you vulnerable to repeated setbacks and embrace a more prudent, strategic mindset that transforms failures into powerful catalysts for growth.

By actively embracing failure as a crucible for learning, rigorously conducting after-action reviews to dissect why things went wrong, meticulously building a failure portfolio to codify lessons learned, and proactively employing tools like FMEA to anticipate and mitigate future risks, you are not just minimizing negative impacts—you are forging a path to resilience, adaptability, and proactive mastery.

This isn't about cautiously avoiding risk; it's about intelligently engaging with it, turning potential pitfalls into stepping stones towards more informed decisions, innovative solutions, and ultimately, undeniable success.

This isn't just theory; it's a proven methodology for taking control of your trajectory and engineering your own triumph.

What’s next?

It’s all about mindset and strategy. As ancient Greek and Roman philosophers taught, we can only control our minds, thoughts, and actions. Focusing on this can help you avoid unnecessary struggle, get unstuck, and move forward faster.

If you need guidance getting unstuck and making crucial mindset shifts, I can help, especially if

  • you are a currently struggling introverted solopreneur (stuck in failure, regret and a flawed mindset that doesn’t serve you)

  • you want to quit your 9-5 job and create your one-person business, but you struggle to pivot (and then regret not making the leap)

DM me on LinkedIn, and let’s explore how Mindset Coaching can help you move forward and claim what you desire and deserve for a life with purpose, meaning and enjoyment.

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