A Red Flag Worth Listening To in the Trough of Sorrow
By now I’m used to hearing all kinds of different expressions of pain from founders as they struggle through the Trough of Sorrow. For the most part, these feelings are simply artifacts of the journey. They don’t usually reveal any deeper meaning about the founder’s motivation and they don’t communicate anything significant about a founder’s underlying psychology.
The helplessness, disappointment, anxiety, and stress that founders feel as they seek out PMF simply reflects the difficulty of the founder’s circumstances, challenges, and stage. The only actions these (very normal!) emotions require is for the founders to recognize them in the moment, to allow them without constraint, to investigate and understand them if necessary, and then to nurture them as-needed as they work their way through the body.
However, there is one thought founders can have in the struggle that reveals something deeper is happening within them. This thought is: “My startup is stealing years from my life. And I want them back.”
Every time a founder has said this to me, I’ve felt the sentence penetrate my body as if I’ve been shot by an electric arrow. It signifies a dramatic shift in the founder’s relationship to their startup and that change is worth investigating - immediately. When founders say this, it reveals that they have psychologically repositioned their startup as if it’s an adversary - an entity who is more powerful than the founder, and one who is stealing precious resources away. A power struggle has been initiated between the founder and their creation. And although this psychological stand-off is somewhat rare, in my experience it has always resulted in the survival of only one of the two main characters.
Founders can enter dangerous territory when this thought is unlocked. They are simultaneously at war with, and trapped inside, the majority-focus of their own life. In this situation, it’s natural to begin to resent your startup, to resent its calls on your time and energy, to resent your employees and their needs, and to resent basically everything about your startup because it’s drawing against an energy reserve that you know is empty. Keep in mind - founders reach this point when they’re already months or years into the grind of the Trough of Sorrow. Reaching this state doesn’t happen overnight - it is reached step by step over time.
So, with the understanding that their energy reserves are shot and yet their startup will never stop screaming for their attention, resentment begins to accumulate in the founder’s mind against their startup. These intense negative emotions position the founder in a toxic internal bind. On one hand, they resent and loathe all of the time and energy their startup is taking from them. But on the other hand, the founders also know they are the ones who ultimately decide where their time and energy is going (at least, they know this intellectually, even if they can’t seem to act on that knowledge).
Founders can really punish themselves when they’re in this bind. They are both the tortured and the torturer - at once, simultaneously. They understand they are the only person who can save themselves and yet they’re helpless to ease the suffering of either position. This painful entrapment can last for a long time (years). It is felt even more intensely if the founder rejects the notion that they can be helpless (as many founders do). This is an inherently self-defeating, disempowered position. The longer it goes on, the more toxic sludge is being pumped through every crevice of the founder’s psychology. It gets thicker and more poisonous over time. When founders’ psychologies remain in this state of self-collapse, multiple additional negative feedback loops are created that reflect this position - founders create even more ways that they are stuck. Here’s a common example of this: A founder knows they’re deeply unhappy, but they are afraid to make a change because they don’t know what else to do or fear the consequences of the change, and because they’re uncertain and/or afraid, they keep working on their startup, which perpetuates the deep unhappiness etc etc...
Talk about a stinky cycle on top of an already difficult situation mixed in with an identity crisis.
Of course, this situation has detrimental effects on the founder’s performance and on the team too. A founder may be less available or intermittently responsive to messages and email. They may miss deadlines, maybe consistently. They may show up to meetings as terse, checked-out, or irritated. When setting goals, they feel deflated and upset by them instead of ambitious and optimistic. Their first thought is, “This feels like so much work” instead of “I can’t wait to try this and see how it goes.” If this happens, they have to drum up some positive feelings to hide their authentic feelings which uses up even more of their energy. They can feel barely capable of doing the minimum, which means they’re not providing their cofounder or direct reports with proactive feedback, they’re not doing 1:1s, and they’re not thinking about their team’s professional development goals. There’s simply no space for them to think about empowering or maximizing their people or their product when they cannot currently do this for themselves.
The founder’s personal relationships and physical health often suffer as a consequence as well. How could they not??
The situation I’ve painted for you is the worst-case scenario.
The medium-case scenario is that founders feel little doses of that resentment and loathing. Maybe you can see yourself sprinkled here and there in the world I’ve just painted for you. But overall, you still feel mostly okay - you have these feelings but they don’t pile up too much, and the situations I’ve described happen infrequently instead of regularly. Even so: Pay attention.
Once founders experience the thought, “My startup is stealing years from my life. And I want them back,” it signals that something important has changed in the founder’s mind and heart. Change is coming. In my experience, the irreversible kind. It’s just that the details haven’t been worked out yet. This thought doesn’t necessarily mean that you are going to leave your startup or that your startup is going to die.
The change that this thought communicates, is that the founder has gained a heightened awareness of their time investment.
You are starting to be more aware of your time investment - including all the big and little things that are drawing down your time - because you're starting to value your time in a new way.
It’s probably a healthier way.
Use this awareness for good instead of evil.
Part of you is coming to realize the time and energy you have innate within you. And how valuable it is. And how necessary it is. And how deeply good it is. This part of you can imagine using that energy for things other than your startup. This awareness is signaling that you want to recapture this and use it to take care of YOU. Which you probably haven’t done for a long long time if you’ve gotten to this point. You’ve probably deprioritized yourself, your needs, your health, your values, and your relationships because your startup has needed your attention instead and you haven’t known how to take care of your needs and your startup’s at the same time. Well, the parts of you that you’ve deprioritized are now the ones screaming out for your attention. Tune into them.
Resentment is inherently a backwards-facing emotion. It turns our attention to the choices we’ve made or to actions done to us in the past. You’ll get stuck and continue feeling badly if you use your resentment for its intended purpose. Resentment will turn us backwards in time, but the past doesn’t always contain answers that will help us going forward. Instead, take note of your resentment but maintain your independence from it. Instead of following its thread and shifting into the past - to all the time “lost” and how your startup did that to you - use resentment to signal your new awareness of the value of your time and look ahead. “I’m angry and in pain about what’s been taken from me” becomes, “I’m aware that what I can give has value and I’m going to give more of myself to myself.” Consider how you could use your time and energy to support you as you move into a new phase, where things are different. They have to be.
Regardless of whether you decide to leave your company, sell, or stay the course and keep working on your startup, this entire experience is a giant flag shaking right in your face telling you that something about your day to day needs to change to be more supportive of you. Your role, schedule, and habits should reflect your needs. The relationship you have with your startup should be one of harmony - not abuse. So whether you make a big change or a many little changes (or both!) I encourage you to really think about what taking care of you looks like in a world that reflects how valuable your energy is.
