Backwards Forward
Here’s the paradox:
Life pushes forward, unstoppable.
To run projects and businesses we need ideas, budgets, goals, and forecasts. This would make perfect sense if we were in control, if “uncertainty” was simply a distant fog in the sea, a blur effect on our glimpse of the future.
But we’re not looking ahead. We have the perspective of a rower. We can only guess where we’re heading, while the past is right there, in front of us. Like the Maori’s “ka mua, ka muri”, we walk backwards into the future.
Our work as entrepreneurs is not to sell a compelling vision. Not even to craft a perfect plan.
Our job is to row harder than most. To figure out where we are through understanding where we’ve been. And to adjust the course as we go until we hit solid ground, only to set out again to claim a new ambition.
How can we plan for a future we turn our backs to?
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1º / 99%
Bear with me as we navigate today’s metaphors. The 1º rule, or “1 in 60”, is a principle that states that a small deviation in direction can quickly compound into big mistakes in the course. A terrifying reminder that small missteps can lead to massive mishaps.
The point(s)?
- It’s a fact that running a business comes with an obligation to keep rowing: innovating, seeking differentiation, competing harder, expanding our customer base.
- We must do all of that and win more than we lose, all while dealing with uncertainty and with what we don’t know we don’t know.
- And we must be bold with some of our bets, knowing that a 1º left unchecked can run amok.
The scenario is set. I’m dropping the anchor on my nautical references.
Let’s talk about managing flexible digital projects so we can do more, better, faster, and more creatively, with proper checkpoints to make sure we can correct the course when needed.
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Expiring decisions
Research shows that roughly half of the projects in B2B will be killed before they begin due to indecision, fear, uncertainty or incomplete information (Dixon/McKenna, Jolt Effect).
This affects everything horizontally: the way I sell services to companies like you, and the way you sell your products to your customers. For every penny you make, you’re missing out on another. There’s a 50% chance that your clients are afraid of making decisions, and another 50% chance that you haven’t invested enough into your selling processes.
And this is most noticeable in digital transformation, ecommerce and online marketing.
I believe there’s a better way to tackle those problems.
Do more: Adopt a culture of experimentation.
Paraphrasing Edison, improving performance is more about perspiration than inspiration. About chasing hunches with a plan and working hard to prove yourself wrong. Instead of gigantic plans and wishful goals, write down brave objectives and create short lived projects.
Do better: Assume things might fail.
Have a more lighthearted view on technology. Projects can tank. Hypotheses can be proven wrong. If you take innovation too seriously, you’ll foster a culture where there’s no room for messing up. And creating new, unexplored shit is messy.
Faster: Nothing lasts in digital.
If you’re looking for permanence, you’re in the wrong newsletter. Today’s Shopify is tomorrow’s Yahoo! Stores (yes, that was briefly a thing). This isn’t failure; it’s shelf life. The secret isn’t to aim for “forever” but for adaptability. Treat every success as a stepping stone—a temporary win that needs to evolve before it expires. Digital is a game of constant iteration: test, learn, adapt, repeat. The sooner you embrace that nothing lasts, the faster you’ll be ready for the next wave of change.
More creatively: A project-first approach.
Our practical advice is to change the paradigm of technology and marketing entirely.
Rather than tasks hierarchies, have projects. Instead of endless meetings and reports up the corporate ladder, have small, nimble teams. Instead of endless or uber-ambitious plans, have focused, easier to measure scopes. Give your teams the bare minimum directions and let them manage their own ideas, decisions and priorities.
With proper checkpoints: Set expiration dates.
Maize’s Tomas Barazza coined the term “Yogurt Organization” to describe a way of working with expiration dates on every initiative. Constraints rock. This self-created one forces you and your team to be pragmatic, fast, and have very concrete checkpoints and KPIs along the way. And it has one particularly magical effect: It helps everyone detach effort from result immediately. It turns the challenge into an exciting race — let’s make shit happen before this expires — while giving you clear rules about what will happen when the buzzer rings. If a project expires, we review it, jot down conclusions, and move on to the next chapter.
Measure, and then measure some more.
Being pragmatic and embracing risk doesn’t mean you neglect responsibilities. Understanding there’s a chance our initiatives will crash means we need clear goals, a shared understanding of what success looks like, transparent scorecards to track all relevant performance metrics, and a plan of what to do when things go south.
By transforming your digital strategies into a project-oriented mindset, you gain multiple advantages. And embrace this idea of ongoing evolution through iteration, instead of the wrong fixed idea of having a website “you only need to revamp every four or five years”. This creates different levels of accountability for your internal team and professional development dynamics. It helps you understand when you need to lean on a third-party friend like my agency vs. when you can handle everything in-house. And because everything comes with an expiration date, it’s much easier (emotionally and rationally) to pull the plug when we see we’re on the wrong path.
A real world example.
The wrong way
In the past few years, I’ve seen literally dozens of companies spend huge portions of their budget on intolerable Salesforce adoptions, followed by a typical case of what you might call “Salesforce regret”. Instead of having small, time-bound projects, the team adopts a massive challenge. A few years and several hundred grands later, they find themselves still struggling to justify the price, and not using enough features.
The right way
If you want to transform anything in your digital stack, limit the project as much as possible and give it an expiration date. Work through this minimum viable idea as hard as possible. At the end, look for what didn’t work. Find the root, and fix the problem. If the team isn’t adopting the tool properly, training and accountability can fix this. If the team is working properly, but you just bought an expensive, overkill mammoth, then count your losses and reshuffle.
In short: The 1º is there all the time. Expiration-led projects limit risk, and checkpoints turn threats into opportunities.
There’s a plan. There’s a culture that helps us cope with fear, because we know things can fail and we’re okay with that. We have ways to tame those small deviations that can turn into big issues. We can conclude that nothing is irreversible, and we can make the right calls, and avoid getting crushed by novelty.
A smooth sea never made a skilled sailor.
If a project is successful, you restart it and sail to new shores. And if not, just say “Oops” and try again, rowing harder.
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Rule of thumb
You should be able to convincingly prove a project within twelve weeks.
That’s enough time to:
- Decide a scope, and the metrics to conclude if it’s successful or not
- Turn the scope into a project, assemble a team and assign leadership
- Prototype, develop, ship, measure and iterate
- Go through the checkpoints (figures, timeframes) to correct the course as needed
Being nimble and accountable is key. When it comes to planning, precision needs to give way to flexibility. The most successful teams I know don’t waste time trying to craft the “perfect” plan—they create a plan to get started. Then, there's no mystery: you just row. The magic is in the checkpoints; when you pause, look at the progress, and make the necessary adjustments when the wind shifts. Because you know it will.
