Time management for early-stage founders
If you’ve ever run a startup, you probably know the sinking, dreaded feeling of time slipping through your hand like a pile of sand. No matter how much grasping, sprinting and prioritizing we do, there never seems to be enough time in the day to accomplish what’s needed.
Is this just an illusion? Are days really so short?
The ubiquitous answer is: “Yes, this is just an illusion! Time is actually abundant! The secret is to work smarter, not harder.” But the popularity of this advice is likely in large part due to its high “advice virality”.
Unfortunately, this advice is not so different than the “one weird trick” that promises to help you lose weight without diet or exercise.
I’m here to blow the whistle: scarcity of time is the stark reality of an early-stage founder, and a founder needs to face this head-on in order to get anywhere.
If it weren’t so taboo to point this out, I think we’d have a lot more successful companies, and fewer founders wondering why they’re so stressed and not making progress.
Pushing the Boulder
Success in building anything, especially a startup, requires pushing a heavy boulder up a hill. Depending on your role, pushing the boulder can mean different things, but it always involves completing tasks that only you can do. You can’t push the boulder by reading, meeting, brainstorming, sitting at your desk, getting groceries, sleeping, exercising or going keto.
The only way to move the boulder is to consistently apply force directly to the boulder — to do the real work.
And if you don’t keep your hands on the boulder, it will roll back to crush you. Lack of progress becomes team demotivation, and eventually exhausts available time, energy and money.
Someday, the boulder will get to the peak of the hill and it can begin rolling down with its own momentum, but that’s a later stage!
Founder Time Budget
Below is a sample time budget showing how much time an early stage technical co-founder might have to actually push the boulder forward in a day:
This leaves a startling 2 hours a day to actively push the boulder. The rest of the time is spent on company maintenance or life.
The good news is this: if you can find 2 hours per day to work deeply on hard problems in your business, you will be doing better than most, and excel. The bad news is: this slim margin causes many to allow themselves to slip into runaway time debt.
Sinking into Time Debt
Let’s examine what happens if the founder experiences a single sick day, using the budget above: The founder will end up with a ~6 hour debt of maintenance work — this is missed work that is required, but that does not move the boulder forward. They also miss their 2 hours of boulder pushing during the sick day.
Paying off the 6 hour maintenance debt requires sacrificing three more days of boulder pushing sessions.
Four boulder pushing sessions total — almost an entire week’s worth of progress — has been decimated by a single sick day!
And what if something else comes up while paying off the time debt? An unnecessary meeting, a flat tire, a technical fire or a trade show? The debt continues to pile up!
To make matters worse, this debt bears a significant interest rate. An overwhelming list of things to do, combined with a lack of visible progress in boulder pushing, leaves founders and teams discouraged. Their ability to pay off their debt decreases by the day until one day they are time and motivation bankrupt.
If you hang around startups, you’ve seen the same unfortunate pattern again and again: people working really hard just to maintain their company, while seemingly getting nowhere. I believe runaway time debt is often the root cause of this.
This also highlights the importance of being able to say “no” to unimportant obligations and opportunities. A day at an unnecessary conference, an unnecessary day of meetings or a bad night of sleep have the potential to set off a disastrous chain reaction.
Mitigation
So — every early-stage founder is teetering on the edge of irrecoverable time bankruptcy. Isn’t that exciting?
Fortunately, those who perceive the utter seriousness of this risk, will usually find ways to mitigate it. Here are a few of the steps I’ve employed to maintain constant boulder-pushing force:
Reserve one entire day each week for recuperation and deep work
Say no to unimportant events and obligations. (Even use this post to make your case on why you need to protect your time, that’s partly why I wrote it)
Ensure you know what your real boulder pushing tasks actually are (often difficult things that only you are able to do)
Delegate anything that you don’t do best
Keep the amount of maintenance work in your personal life to an absolute minimum. Use good procrastination on errands that can be pushed off. Many tasks such as cleaning, cooking, grocery shopping and filling the gas tank, are more efficient to do in larger batches less frequently.
Be scrappy (strategically cut corners where possible)
The next comments go counter to popular self-help wisdom, but for me, they are the most important learnings, because they go unspoken. This advice may be perceived as taboo:
Put in extra evening/weekend time to pay off time debt when you sense it’s starting to pile up
Don’t work when totally burned out. Figure out what you need to get into a productive mindset (sleep, exercise, food, mental rest). But note that you can ultimately never relax or vacation your way out of time debt — and trying to do so can be quite stressful as you feel your debt accumulate exponentially. Relaxation comes naturally when your debt is manageable or paid off.
Caveat
I asked my friend Joe Teo to review a draft of this post, and he pointed out a really important caveat: pushing the boulder means very different things at different stages of a startup, and a failure to recognize that shift can also be devastating.
On day zero of a startup for a technical founder, pushing the boulder may strictly mean programming, but if that founder continues to believe that’s their job with a team of 20+, they’ll be in for major trouble. More and more, the job becomes about enabling a team to consistently push the boulder — the founder’s boulder then consists of management and directing the vision.
But while the mistake above is made frequently, it is has typically been discussed more openly. This article was aimed at illuminating a more taboo truth from the earliest stages: there really is no time.
Note: I wrote the first draft of this during the earliest stages of Rally, where it was just 3 co-founders hacking away with no VC backing. That is the context where this advice is most relevant. I’ll be reflecting back on this, and updating it, as Rally grows.
Scott is the co-founder and CEO of Rally, a legaltech software company which seeks to save significant lawyer and founder time.