Strategy is the “what”, planning is the “how”, and monitoring is the “Are we still on track?”—and most small businesses only ever do the second part. This episode of the Meaning Business Podcast challenges owners to flip that, and deliberately design both business and personal strategies so the future doesn’t blindside them.
Why small business owners must stop “just doing the doing” and start leading with strategy, backed by practical stories from fuel stations, Uber and adventure racing.
Most business owners are drowning in activity but light on direction. They have annual budgets, project plans and to-do lists, yet no clear strategy that tells them what game they’re playing or how they intend to win. The episode frames this simply: strategy sets direction; planning organises effort; monitoring keeps you honest when reality changes.
In practice, this means deciding upfront whether you are competing for fun, survival or the podium in your “race”—and letting that choice shape everything from your pricing to hiring to hours of operation. Without that strategic choice, every new opportunity looks tempting, and you end up chasing “butterflies” instead of building momentum.
Strategy vs planning vs monitoring
What is strategy?
Strategy answers the big “what” and “why” questions:
- What kind of business are you building and why?
- Who are you serving and how will you be different?
- What trade-offs are you willing to make?
The hosts describe strategy as the anchor that dictates every other decision, from what markets you play in to what you deliberately ignore. It is not a 40-page document full of buzzwords; it is a clear, conscious set of choices that can be changed when new information emerges.
What is a plan?
Planning is about execution detail—the “how”, “when”, and “who”. Once the race strategy is set—compete hard, go mid-pack, or just finish—the plan covers routes, checkpoints, nutrition, team roles and contingencies. In business, that translates to:
- Marketing calendars and campaigns
- Hiring plans and org charts
- Operating procedures, budgets and project timelines
Plans are only useful to the extent they support a deliberate strategy. A beautiful plan with no strategic backbone is just organised floundering.
Why monitoring is the missing third piece
The episode adds a third essential element: monitoring. Monitoring turns strategy and planning into a living system by forcing you to:
- Measure what matters (daily, weekly, monthly)
- Listen to customers and the market
- Decide when to adapt the plan or rethink the strategy
Without monitoring, you make changes ad hoc—driven by emotion or panic—rather than by evidence. With monitoring, you gain the confidence to stick to a good strategy when it’s working, and the courage to change direction when it is not.
Adventure racing: the perfect metaphor
Choosing the race you’re in
The adventure racing story in the episode is more than entertainment; it’s a mirror for how many owners run their businesses. The first race the host entered was chaotic: last-minute team changes, no real prep, and a route full of poor decisions that left easy points on the table. The team finished, but nowhere near competitive.
The lesson was simple: before you design the course (plan), you must choose your race strategy:
- Race for fun
- Aim for a respectable mid-pack result
- Go all-in for the podium
Each strategy leads to different decisions about training, teammates, equipment and which checkpoints are worth the effort. Businesses that skip this step end up chasing every enticing “checkpoint”—new product, new market, shiny opportunity—and burning energy without progress.
Avoiding the “pretty butterfly” detours
On the course, someone always spots an attractive checkpoint “just up the hill”. Without a clear strategy, the team gets seduced into detours that cost time, energy and morale. With a clear strategy, the decision becomes objective: does this side quest help us achieve what we said we were here to do?
In business, this is the difference between:
- Saying yes to every new idea because it’s nearby
- Saying yes only when it aligns with the strategic goal (e.g., high-margin, niche positioning rather than raw volume)
This disciplined “no” is where strategy protects you from your own optimism.
The fuel station: high volume vs high margin
A conscious strategic pivot
One of the strongest stories in the episode is a service station that could not pay its rent, despite selling around 600,000 litres of fuel a month at a tiny margin. The owners made a deliberate strategic choice: sell less fuel at a higher margin and turn the shop into a true profit engine.
The new strategy: accept lower fuel volume but raise price and focus on improving gross profit per litre and per customer. With that set, the plan became concrete—adjust prices, reposition the store as a destination, refine product mix and service, and rethink operating hours.
How monitoring kept them honest
Critically, they monitored everything: sales patterns, customer reactions, shop turnover and profitability. This allowed them to:
- Confirm that higher margins were offsetting lower fuel volume
- Protect and then grow shop sales by designing a better in-store experience
- Decide whether staying open 24/7 still made sense financially
Because they had a clear strategy and a measurement rhythm, they could test the new approach without betting the farm—and could have pivoted back if the numbers did not stack up.
Uber, London cabs and strategic innovation
Uber: changing the game, not the paint job
The episode contrasts traditional taxi operators with Uber to show what real strategic innovation looks like. Taxi drivers competed on marginal differences: cleaner cars, friendlier service, better hours—none of which changed the underlying business model, pricing controls or customer experience.
Uber’s strategy was entirely different: leverage existing private vehicles and drivers, build a digital platform, and redefine how riders request, track and pay for trips. Planning then focused on building the app, scaling driver acquisition, and navigating regulatory threats—clear “how” work in service of a bold “what”.
London cabs: design as strategic weapon
The discussion of London’s iconic black cabs highlights a more subtle strategic play. The manufacturer decided to become the benchmark vehicle for urban professional transport—not just “another car”. That strategic stance drove countless design choices:
- Passenger-centric visibility through window height and glass roof
- Door and cabin geometry optimised for easy entry on busy curbs
- Interiors that can be quickly cleaned after late-night crowds
These decisions reflect a deeply thought-through strategy: build a vehicle that outperforms generic cars for both drivers and passengers, and in doing so, compete more effectively with ride-share platforms and alternatives.
Why most small businesses have no real strategy
The “just run harder” mindset
Despite the clear value of strategy, the hosts note that only a tiny fraction of small and mid-sized businesses they see have a genuine strategic business plan. Owners are often too busy “doing the doing” to step back and decide where they are actually going.
When advisors raise topics like vision, mission and strategic direction, many owners switch off, dismissing it as corporate buzzword fluff that does not apply to them. The result is a style of management that resembles ancient warfare: two armies running at each other, hoping the bigger one wins, rather than using intelligent tactics and positioning.
Emotion vs logic
Emotional decision-making is another barrier. Without strategy, emotions—fear, excitement, ego—fill the vacuum. Owners chase revenue for its own sake, react impulsively to competition, and make investment decisions based on mood rather than metrics.
The episode argues that strategy creates a logical frame to contain emotion. When there is a clear direction and planned measures of success, decisions can be tested against “Does this move us closer to our defined outcome?” rather than “How do we feel today?”.
Business strategy and personal strategy must align
Two strategies, two plans
A powerful insight from the episode is that every owner needs both:
- A business strategy and business plan
- A personal strategy and personal plan
Starting with the personal side clarifies why the business exists at all. Do you want time freedom, generational wealth, philanthropy, adventure, or a stepping stone to another project? Money is rarely the end; it is usually the means.
Once that personal strategy is clear, the business strategy can be designed to support it: revenue targets, role design, timeline to exit, and risk appetite all flow from what you want your life to look like.
Value-building vs sale-ready strategies
The hosts distinguish between value-building and sale-ready strategies for business owners.
- Value-building strategy: Focused on increasing profitability, reducing dependency on the owner, and creating robust systems, people and products so the business becomes more valuable over time.
- Sale-ready strategy: Focused on making the business attractive and easy to sell within a defined timeframe—clean numbers, stable leadership, clear processes and reduced owner reliance.
Both approaches require deliberate planning and disciplined monitoring but start from different strategic outcomes: long-term compounding value vs. near-term exit.
Sub-strategies: HR, marketing, finance and beyond
Strategy is not one big sentence
The episode stresses that “business strategy” is really a cluster of aligned sub-strategies. At minimum, you need clarity in areas such as:
- People and culture (HR strategy)
- Finance and cash management
- Marketing and market positioning
- Operations and systems
For example, a people strategy that leans on high trust and autonomy requires hiring self-managing professionals and building lightweight management structures. A more hands-on, accountability-heavy strategy calls for robust processes, tight KPIs and structured oversight.
Every expense tells a story
One of the advisory insights shared is that every line in the profit and loss reflects a story and, behind that, a strategic or non-strategic choice. Rent, wages, advertising, subscriptions—all of them should make sense in the context of your defined strategy.
If your strategy is “high-margin, high-service niche”, your spending should reflect premium positioning, expert staff and experience design. If it is “low-cost, high-volume”, the pattern of expenses should look very different. When the P&L and the stated strategy do not match, the plan and monitoring cycles need to be revisited.
Working on the business, not just in it
Making time for strategy
The familiar advice to “work on the business, not just in it” takes on new weight in this context. Working on the business means:
- Clarifying and refining strategy
- Translating strategy into concrete plans
- Setting up monitoring rhythms and dashboards
Without this, even growth can be deceptive: you might increase turnover while building a brittle, owner-dependent business with limited resale value.
Strategy as energy and protection
The hosts point out that a clear strategy is energising. It gives reason and direction, making daily work feel purposeful rather than chaotic. It also acts as a protective filter, shielding the business from distractions, vanity projects and misaligned opportunities.
In uncertain environments—economic shifts, technological disruption, regulatory changes—strategy and monitoring together become your early warning system and response playbook.
Key takeaways
- Strategy is the “what and why”; planning is the “how, who and when”; monitoring is the disciplined check that keeps both grounded in reality.
- You can (and should) change strategy when evidence shows it is not working—but those changes must be driven by monitoring, not mood.
- Real-world examples—from failing fuel stations to Uber and London cabs—show that strategic shifts in model, margin or design can unlock disproportionate gains.
- Most small businesses lack a true strategic business plan and rely on effort, emotion and habit instead of thoughtful direction.
- Every owner needs both a business strategy and a personal strategy; the business should be designed to serve the life, not the other way around.
- Sub-strategies in HR, marketing, finance and operations ensure that day-to-day decisions line up with the overarching direction.
- Working on the business—strategy, planning, monitoring—is what separates the small minority who run by numbers from the majority who simply react.
Callout:
A plan without strategy is motion without meaning. A strategy without monitoring is confidence without proof.
Real-world applications for your business
Step 1: Define your race
Decide what “winning” looks like for your business over the next 3–5 years:
- Dominate a niche at high margins
- Build a lifestyle business that funds your life with minimal stress
- Grow and exit at a specific valuation
Write this down in plain language. This is the seed of your strategy.
Step 2: Design your sub-strategies
For each core area, answer: “Given our overall strategy, what does this function need to achieve?”
- People: what kind of team and culture?
- Marketing: which market, message and channels?
- Finance: what margins, cash buffers and investment pace?
These become your sub-strategies and will directly shape your plans and budgets.
Step 3: Build simple, living plans
Translate each sub-strategy into 90-day plans:
- 3–5 key projects per quarter
- Clear owners and milestones
- Specific metrics to monitor (daily/weekly/monthly)
Make review and adjustment a normal part of your leadership rhythm, not a yearly event.
Conclusion and suggested call to action
Future-proofing your business is less about predicting the future and more about building a strategy–plan–monitor cycle that lets you adapt faster than everyone else. The stories in this Meaning Business episode show that when you make conscious strategic choices and back them with practical plans and disciplined monitoring, you stop floundering and start leading your market.
A practical next step: set aside two uninterrupted hours this week to draft your personal and business strategies on a single page, then identify three metrics you will monitor monthly to check if you are truly on track. If you have an advisory partner or mentor, share that draft with them and commit to reviewing it together every quarter.
How can we assist you?
At Benchmark Business Advisory, we work with business owners who are great at what they do but often caught in the day-to-day of keeping things running. Our job is to help them step back, see where their business has slowed, and find the spark to move forward again. Whether they want to prepare for their next phase of growth or get their business ready for sale, we help owners renew energy, sharpen focus, and build momentum — so their business doesn’t just keep operating, it thrives with vitality.
Video Podcast Episode Link: CLICK HERE