Failure Is Inevitable: How to Fail Forward and Cheaply

Failure Is Inevitable: How to Fail Forward and Cheaply

"The credit belongs to the man who is actually in the arena, who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming." Theodore Roosevelt

Roosevelt must have been talking about successful small businesses. Failure is inevitable when operating a business day in, day out—but it’s also your secret weapon. Small businesses can turn setbacks and stumbles into sprints and advantages without breaking the bank.

Failing forward? Failing forward and cheaply? That's the fine art of minimizing costs while maximizing lessons. Think micro-experiments, not major gambles. Functional prototypes over polished perfection. Customer feedback loops that don't drain your resources.

Why Failure is Inevitable in Small Business

If you're running a small business, you're navigating a minefield. Failure isn't just a possibility—it's practically baked into the recipe. Here's why:

  • Market volatility: trends and demand shifts
  • Economic curveballs: recessions, inflation, supply chain chaos, etc.
  • Tech disruptions: what's cutting-edge today may be obsolete tomorrow
  • Ruthless competition: new players coming onto the scene with deeper pockets

Add in your limited resources and the steep learning curve of entrepreneurship, and you've got a perfect storm for setbacks.


What Is Failing Forward?

The art of turning every failure into fuel for your next success, learning and adapting with each setback to propel your business further. This isn't your average failure. It's strategic and intentional. For small business owners, it's your unique crack in the code for all things marketing and operations.

Failing forward means:

  1. Testing ad campaigns on a shoestring budget
  2. Pivoting your product based on real customer feedback
  3. Iterating your operations until they run like a well-oiled machine

Strategies for Failing Cheaply

Small businesses usually have big dreams but a more limited wallet. For some this might cause more problems, but not for you. Let's talk about failing so cheaply it feels like you're stealing lessons from the universe. As a small business owner, you should become very familiar with Minimum Viable Products (MVP). They are the ticket you need to test the waters of your operating dreams without drowning yourself in actual debt.

Examples of MVPs in small business include:


  • A bare-bones version of your product/service (bells and whistles to come later, post-refinement and proven success)
  • Just enough features to be usable (again, bells and whistles can wait)
  • Designed or executed to get maximum customer feedback with minimum effort



A/B Testing

Think of A/B testing as a low-cost casino where the house (you) always wins.

This requires split testing everything in your operation to find exactly what works and converts:

  • Email subject lines
  • Affordable microsite/landing page design
  • Product descriptions
  • Pricing structures

A Lean Startup Methodology

Acting like a lean startup is not just a strategy for tech bros.

Adapt it to your small business:

  1. Build (quickly and cheaply)
  2. Measure (remember, data, data, data is your new best friend)
  3. Learn (pivot or persevere based on cold, hard facts)

Every dollar you save on failing is a dollar you can invest in succeeding.

Keep iterating, keep learning, and keep pushing forward because (a little-known secret) the path to success is paved with cheap failures.

Mindset Shift: Embracing Failure as a Learning Tool

A common misconception is that failure is the enemy. Failure isn't your enemy; it's your most brutally honest mentor. Every “failure” in business is just a personalized masterclass in what doesn't work. Put another way, it’s priceless intel for what will work. Creating a culture of experimentation in your small business is how you survive the cutthroat pace and game.

Here's how:

  1. Celebrate each and every attempt, not just the wins. Reward bold moves, even when they flop.
  2. Make "I don't know, let's find out" a team mantra, especially amongst leadership.
  3. Set aside resources—time and money—specifically for experiments.
  4. Share failures openly. Make them badges of honor, not marks of shame.

Shift of mindset

Learning From Missteps

Once a mindset shift has taken place, you need to actually put your change of mind and attitude to action.

There are several ways to go about this:

Conduct effective project or trial run post-mortems:

  • Schedule these post-mortems immediately. No time for wounds to fester.
  • Focus on the processes, not the people or uncontrollable factors. It's about what went wrong, not who screwed up or how it was a good run of bad luck.
  • Ask "why" five times and get to the root cause of what exactly failed.

Identify actionable insights:

  • Look for patterns across failures. That's where the gold is.
  • Quantify the impact. What did this failure cost in time, money, opportunities?
  • Identify the early warning signs you missed.
  • Ask: "What would make this idea/product/service work better next time?"

Implement changes based on lessons learned:

  • Create a failure log. If this is done with utmost honesty and respect for the process, it can become your playbook for future success.
  • Build feedback loops to check if implemented changes are working.
  • Revisit old failures regularly. New perspectives and time away can unlock hidden lessons.

Your mindset is your most powerful tool. Sharpen it with every failure.

A Real World Example

There are people running businesses who are failing forward around you all of the time, even if it doesn’t seem like it. For example, there’s a small vehicle towing company in Colorado that has been operating since the late 90s. Business was booming and they were cruising right along until BAM! A big competitor rolled into town, threatening to steal their customer base. Terrified, it felt like their businesses’ success was up and they were ready to throw in the keys. So much so, they considered the thought of shuttering because they felt like there was simply no way to compete. But after many days of contemplation, they decided to “fail” forward.

failing forward business


The Cheap Fail-Forward Move

Instead of over-reacting to the situation by throwing money at traditional advertising or slashing their prices, the small towing company got smart. They decided to redirect all their marketing efforts and instead, go all in on SEO by hiring a super affordable Montrose SEO company. As a result, that SEO agency had a deep focus on dominating local search results for "Montrose tow truck driver near me".

The Results

It turns out that the competition coming to town was a blessing in disguise. Instead of the new competition eating the existing towing company’s lunch, they:

  1. Saw higher rankings in local Google searches
  2. Increased visibility to potential customers in crisis
  3. Got more calls and more business, all without breaking the bank or going belly up

A Towing Company’s Key Takeaways

  1. Think Digital First - Old school isn't always best. The towing company could've wasted cash on expensive marketing material or town event sponsorship to stay in the local’s favor. Instead, they invested right where their customers were searching.
  2. Niche Down - They didn't try to out-market the big guys across the board. They laser-focused on local SEO to carve out their territory.
  3. Leverage Expertise - By hiring an SEO specialist, they multiplied their impact without multiplying their costs.
  4. Play to Your Strengths - As a local company, they emphasized their Montrose roots in their SEO strategy, connecting with the community in a way big chain competition couldn't.

The Fail-Forward Lesson

Sometimes, the best way to compete isn't to match your opponents blow for blow. It's finding the gap in their armor and striking precisely. This towing company didn't just survive; they thrived by failing forward into a smarter, more targeted marketing approach. They turned their small size into an advantage, becoming the go-to local option for the local residents in need.

The Arena Awaits: Your Failure Playbook

To fail forward cheaply, remember:

  1. Failure's Inevitable: Embrace it as part of the plan, not a dangerous enemy.
  2. Fail Forward: Transform setbacks into motivation and cause for change and improvement.
  3. Budget-Friendly Flops: MVPs, A/B tests, lean methods—your low-cost, high-impact tools.
  4. Mindset: Allowing fear to overcome you is the real failure.
  5. Lose or Learn: Post-mortems, insights, rapid changes, plenty of reflection—your competitive edge.

Man in arena

Now, as you step back into the arena of small business, remember this: you're not just running a business; you're conducting experiments in success.

So go forward.

Fail spectacularly, fail often, fail cheaply.

Because in the end, the credit belongs not to the critic on the sidelines, but to you—the one in the arena, daring greatly, failing boldly, and rising again and again.

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