Oliver Gilan

Thinking Short and Long

I often hear founders and investors talking about the need to think short and long—to zoom in on the daily details and to zoom out on the big picture strategy—as key skills for a founder. I think it’s great advice if not a little obvious but the way these skills come into play changes over the lifetime of a company in a way I didn’t fully appreciate before.

In the beginning of a new company you will have a guiding vision but by far the most amount of your time will be spent laying the bricks of your foundation every single day. It may seem on the outside that you are immersed in the big picture vision because that is what you will discuss whenever you talk to investors, customers, or family but the majority of your time will be focused on the daily grind. At such an early stage there is little need to zoom out and analyze the big picture compared to how often you need to be zoomed in and executing relentlessly. Navigating a ship doesn’t matter much if you don’t have a ship!

On the other side as you are approaching an exit it becomes far more important to spend time zoomed out, analyzing the bigger picture, and strategizing effectively. Solving day-to-day problems will be less of your concern and you will need to be capable of seeing the bigger dangers and opportunities. Hedging risks against economic black swan events, capitalizing on new opportunities, and managing the growth of your business all require a clear vision of the future beyond the daily work that needs to be done. You will need to think long to navigate your ship through uncharted waters.

These skillsets and their value seemed obvious to me for the longest time but recently I’ve come to realize there is a third distinct skill that you don’t get for free just by being good at the other two. That is not just thinking short and thinking long but to do both at the same time. This is so difficult that it separates itself as a skillset from the other two individually and is one of the defining hardships in the Trough of Sorrow.

After you’ve attained product-market-fit but before you are on the path to an exit you will spend the majority of your startup’s lifetime in the trough of sorrow facing a seemingly endless road of hardships and struggles. As you scale the tricks and shortcuts that got you here—and you will have tricks and shortcuts otherwise you wouldn’t be here—will begin to slow you down. Your abstractions and data models will show their limitations, your bugs and ops load will increase, your morale will decrease, and your velocity will slow. Your ship will begin to spring leaks. You will have to dedicate a significant amount of your focus day-to-day fixing those leaks while at the same time the challenges of scale will require more deliberate long-term thinking.

On paper the margin for error may be bigger than in the past but the opportunity cost of a wrong move will be higher than ever before. Incumbents will begin to treat you as a real threat and deploy resources—sometimes more than you have—to destroying you while new competitors that are still young and agile will pop up around you. Big ships turn slowly and in such an environment you are only afforded so many wrong turns before you’re left in the dust. A month or two pursuing the wrong approach early on may not be a problem because you can pivot in a day but that agility will rapidly disappear as you scale. A random walk approach to solving your problems will not be a sufficient strategy for this phase because your growth turns your local maximas into tech debt, your tech debt amplifies the leakiness of your foundational model, and the weaker the foundational model the slower you become, the more firefighting needs to be done, and the worse your position becomes relative to competitors.

This is the time to escape your local maximas. Plans will need to be made on the scale of months but executed on the scale of days. The nature of escaping local maximas means your plans might not show meaningful returns on investment for longer than ever before making it hard to guage the effectiveness of new strategies. You will need confidence to stick to new initiatives for long enough while also having the humility to understand that any given course of action could be wrong. Full rewrites of your codebase will become attractive options just to get back to the feeling of high velocity but this is a trap in all but a few instances.

The hardest part about engineering isn’t building the initial system it’s changing it in motion. Part of thinking short and long is recognizing what you have here and now and where you need to be long term and then executing on a plan to reduce the delta. This is difficult in a way that academic program design and brute-force programming usually fails to capture. Refactoring often leads to bugs and you’ll be suffering with enough of those. Sometimes it’s not clear that refactoring in a specific way will help and sometimes it feels very clear but there aren’t definable metrics. It’s very tough to convince people that things should be done a different way if you cannot point to immediate quantifiable ROI on the work required to change the system. If you’re the founder or in a position of leadership you may think that you don’t have to convince anyone but there’s always stakeholders beyond yourself and at this stage of your company’s life you may find yourself with more stakeholders than you realize.

Working at a company during this period can be brutal for non-founders as well. Foundational employees are likely to leave at this stage and take with them critical institutional knowledge while increased ops loads and longer timelines for progress will lead to burnout amongst the employees that remain. You are most likely to burn out at this stage too. The headcount of the company will grow and change leading to internal politics that need to be managed for the first time in the company’s history. Lines of ownership will be drawn, formal processes will be implemented, and accountability will be quantified. In many ways the fun part of an early startup will rapidly vanish but the abundance of a large established corporation will not exist yet leading to the combination of boring cog-in-the-machine work environment without the margin of safety to go along with it.

You may become increasingly frustrated with your own ability to get things done. Your time context switching between daily tasks and big picture planning will prevent you from doing either one as well as you’d like. To properly strategize long term you need uninterrupted time to understand and map out the landscape ahead. To properly move the needle on high impact daily tasks you need uninterrupted moments of flow. But your time will be interrupted. Your calendar will fill up and your responsibilities will multiply and you will find yourself without the time to work on the high impact daily work you’re used to doing and you will be frustrated at your own lack of focus at seeing the bigger picture. This feeling of deteriorating excellence due to having one foot in both worlds will seemingly come at a time when the issues your product and company face become more apparent than ever and the solutions needed more obvious. This decreased effectiveness combined with a growing list of problems leads to the sensation of slog and it will stretch out before you like a road that disappears across the horizon.

The worst part about this stage is you might do everything right and still lose but that’s just the nature of things. There’s no way to know until you try. If you’re an employee at a company in this stage more will be asked of you than perhaps you signed up for but there will also be incredible room to grow. Simply showing up every day and executing relentlessly can be the difference between success and failure. If people feel they can rely on you to do what you say you will do that eases the load off everyone that you work with. Dependency means

I have no advice to give about how to get through this period of time not because I don’t have ideas on what would help but because I don’t have the experience to know if they’re right. It would be disengenuous. All I can do at this point in my career is observe and learn and hopefully in 10 years I can definitively write about the strategies that make this period of a company’s life easier to get through. What I do know is that the skillset required to get through this period is distinctly different than what is required before and after it. You will need to think short and you will need to think long and you will need to do both every day all the time. I do know a good team that you trust is critical—I don’t see how you can possibly survive without that—and you will need to pace yourself. Now more than ever the game becomes a marathon not a sprint. The only way out is through.