The mental game

Of all the great challenges that pave a founder’s journey, perhaps the toughest of all is learning to play - and win - the constant mental game that comes with the job.

Mental games come in many forms, and each day in the life of a founder brings with it new antagonists, with their unique flavours of ruses and tactics. Below, I list the main culprits I’ve noticed in my own life and offer a few strategies that help me defeat them.

Procrastination

Writer’s block, “ideation” sessions, endlessly re-cleaning your house, cooking healthy meals, consuming “educational” content, or working out to feel productive - this is your mind pulling you away from the work.

• How to defeat itWork in blocks, stick to a schedule, use your calendar as a to-do list. If working from home, get out of the house - to your local coffeeshop or library. I've also found that I procrastinate substantially more when the task on my to-do list is broad / blurry - making it unclear where to start (e.g. "write a blog post", "build a feature"). A great way to overcome this is to set some time aside every day to break down your tasks into smaller, more tactical chunks ("write section X including anecdote A", "implement the login flow"). And by all means - keep exercising, eating healthy, and cleaning your house - just not as escape mechanisms from the real work.

Comparison

This is a big one; a friend gets a new job or a promotion, LinkedIn announcements left and right, a fellow founder celebrates a key milestone and your competitor announces their latest fundraise - all while you’re struggling to get traction / fundraise / hire and anxious about runway.

• How to defeat itYou need to realise that (1) your employed friends have other problems (bullshit jobs even if they look good on paper, building someone else’s vision, less agency/freedom, capped earnings), and (2) the struggle of your founding journey is precisely the reason why most people stay in their comfort zones and never dare to start a company. The struggle is the price you pay to get a shot at building something great. Focus on your next step.

Rejection

Rejection can come from anywhere: customers, investors, potential hires, but also friends, family, and people you meet at networking events or coffee chats, all of whom can be ruthlessly effective at explaining to you in 25 different (and surprisingly creative) ways why your startup is bound to fail. The risk with rejection is how easy it is to start believing all the feedback you receive and give up on your idea (or course-correct too much, which leads to inconsistency and lack of focus).

• How to defeat itBuild an unshakeable inner compass, and reinforce it frequently. You need to know why you’re doing what you’re doing, and have deep conviction that it needs to be done. Keep a log of every piece of pushback and criticism you receive, and make time once a week / fortnight to review new entries and explain why they’re wrong / what they’re missing. If you can’t come up with a satisfactory explanation, chances are that piece of feedback is valuable and should not be ignored. Crucially - work on your story! Steve Jobs spent 2 years refining the iPhone story before it launched; over time, your pitch will get better and people will get on board with your vision.

Shiny object syndrome

Linked to comparison, shiny object syndrome is the FOMO you feel when you see someone else working on a problem that seems more promising, interesting, or important than the one you’re working on. It is particularly prevalent in a hot market like the current AI cycle, where mind-boggling fundraise figures and growth rates can make it look like the great ideas are all around you.

• How to defeat itSimilar to the rejection strategy above - build an unshakeable inner compass and deep conviction for what you’re doing. Crucially, cultivate your conviction with a daily practice of “remembering” (I recommend looking into hypomnēmata - a combination of meditation, writing, and visualisation techniques to help keep the important things in your life front of mind). Besides - if your company only exists because it looked cool when someone else talked about it, you’re likely working on the wrong thing.

Negative self-talk

In the same way an athlete can be thrown off when they lose a game, all of the above mechanisms can trigger harmful self-talk and throw you into negative spirals, sometimes leading to anxiety, isolation, or depression.

• How to defeat itInternalise the fact that the mental game is the journey. It is also infinite, and losing it today says nothing about how you’ll play it tomorrow. Remember that throughout his career, Federer only won 54% of the individual points he played - yet he won 80% of his matches. The key is to be kind to yourself, and to view each failure as a datapoint to be fed into your next play - giving you a better understanding of your triggers, thought patterns, and the habits that will help you win the mental game more consistently.

The mental game never ends. The trick is to accept it as an inherent part of the founder’s journey - and to get comfortable playing it. In Josh Waitzkin’s words - settle in.