The Power of Unlearning for Later Stage- and Serial Founders

Olga Skipper
5 min readMar 1, 2021


Photo by Kristopher Roller on Unsplash

When we embark on the founding journey for the first time, we are usually in our twenties. There is a lot of space for everything. And this is the time when our company becomes that “everything.” We sleep in our offices, order lunch every day, and forget how to cook ourselves, we hang out with our cofounders, and really the grinding and building takes up the whole space.

If we are balanced enough, we would include physical activities, maybe vacations (usually short and sometimes with our cofounders;) but that’s really it. It feels like a challenging and fulfilling journey among our new family — our company.

Yet comes a moment when the balance shifts, and this habit of making achievement - our whole life, stands in our way rather than accelerates us.

What changes

At some point, your company grows (up), you move into your thirties, where other aspects of life become more important: like creating family, health. On top of that, the complexity of the tasks you are dealing with increases, your role as a founder changes dramatically for you to become a CEO.

Everyone has their own trigger when they start looking for new role models, those that managed to build bigger lives that include their companies but are not limited by them.

You also might notice it physically. For years and years, you’ve been pushing yourself and lived within a Cortisol+Dopamine loop (sympathetic state), neglecting the oxytocin (parasympathetic state). In plain English, you didn’t have enough time to rest. And it becomes harder and harder to put your laptop away, switch off, and fear and anxiety become familiar to you.

The trap here is to think that you need to choose… either life or company, either energy or success, either joy or work results.

The real expansion here happens when you understand that you need to start unlearning certain habits to create space for a new life of both fulfilment and success.

The Unlearning

If „achieving“ is your Modus operandi, the Unlearning is hard. Your neural pathways are now created in the way that switching off your email at 8 pm doesn’t work. Your hand grabs your phone and wants to know what emails came in automatically; you don’t even need to think of it. The same happens with our leadership styles, the way we make decisions, the way we build relationships. What served you as an early stage or first-time founder, might be damaging later on.

The second reason what makes it hard is that you don’t know it will work and keep you a) successful and b) fulfilled. The risks that you feel are higher than the gain.

Both the structure of your brain and your fear can hold you back from the life you want. Yet there is a way out.

What to do with it

First, you need to rethink what activities you call work.

If before your role as a founder could be described with a single word, for example, “doing” or “achieving,” or even “my baby,” now your work consists out of 3 core activity clusters “Create-Recharge-Reflect.”

Unlearning here really means that you stop treating recharging and reflection as an EXTRA that you do outside of your work.

Secondly, you need to understand that “recharging” is not extra. Recharging is now a part of your work, especially because the complexity of your work increases exponentially. You need to split between recharging and timeframes such as your weekend or vacation (for example, if you have other responsibilities outside of work).

Thirdly, you need a solid reflection routine. Again, as with the “recharging,” it is not an extra anymore. With the increased complexity, your brain (and if you are already further down the path — your cognitive, emotional, physical, and spiritual intellects) requires time to sync and process everything you observe and experience.

To make sure you are creating a sustainable change, you must take a step-by-step approach. Don’t try to change everything at once. You need to gain trust in the new way of living, build new neural pathways and find your own methods that work for you. For the new way of living to be created, you need repetition and trust, so start small and increase intensity over time.

To help you navigate this change, below, you will find a practical how-to. This how-to is deliberately structured as a list of references and links. Choose where you want to start and dig deeper into the theory or approach behind it. And if you have any questions — don’t hesitate to reach out.

“Create-Recharge-Reflect” — the How-to

Here are some practical steps that you can take:

  • Shift your focus from time-management to energy management. Observe how your energy changes during one day, one week, monthly cycle. What recharges you, what drains you, when are you most productive, and when is it better to switch into recharging.
  • Notice when your head gets full, you might be missing some reflection time. More on it later.
  • Work only in your personal Zone of Genius. I know this is scary; first, learn to drop the tasks in the Zone of Incompetence and the Zone of Competence.
  • Make sure you understand what you 1. Control & 2. Influence and what is the difference between the two.
  • Say no to meetings that you shouldn't be a part of. At this point, you have enough experience, power, and a well-developed gut feeling to know how to select those that matter.
  • To the same point – stop working with people that drain your energy. (full stop) If you are not yet ready for that, first say no to those that drain your energy with no additional benefit for you and your company.
  • Become an “adult” in your work relationships. No babysitting, no lifting others. They are adults as well. Let them step into their power.
  • Understand you need strong relationships outside of your company. Because you also need to understand your company is not “your family” anymore.
  • Learn what gives you joy (aka oxytocin and puts you into your parasympathetic state). And continue discovering new ways if old ones do not work anymore.
  • Get some sleep. You might be surprised, what version of yourself you will experience after 8–9h of solid sleep. It will save you much more time during the day and keep your head clean.
  • Reconnect to your feelings and the body intellect that you neglected. In the early stages, you need to push through and “suck it up”. Now you need the wisdom and the data of your feelings and your body. It can be as simple as yoga, running, embodiment coaching, body therapy, etc.
  • Pick up a mindfulness routine. It doesn’t need to be meditation; start with observing whether you breathe enough. I see a lot of startup founders forgetting how important that is. It can also be a walk in the woods, cycling alone, playing ping-pong even (very good for ADHD treatment btw), find your own way to reconnect with yourself.
  • Blocking time during the workweek, journaling, peer-coaching, executive coaching, etc., can be a great start to reflection. Track progress and changes. To gain trust in the new way of living, you need to start seeing its benefits.

And definitely many more.



Olga Skipper

Executive coach and Advisor for Tech Founders and Entrepreneurs. Asking uncomfortable questions.