The Part that Nodody Sees
I’ve thought about writing a post about founder mental health for a long time (like two years to be precise.) I’m not sure what compelled me to finally do it this month. Maybe it was the cosmos or I was just feeling extra introspective in the new year. Either way - here we are.
The thoughts that I’ll share here are the culmination of much scattered journaling and writing from the last several years while building indiFIT and Maloka. Writing all of this down has been therapeutic because it helped some common themes to emerge. Those themes have a way of bringing order to what can otherwise feel like a tangled web of thoughts and emotions. Giving those thoughts and feelings names can help to more mindfully notice them, process them, and pattern match to them when you they pop up again.
My hope is that if you’re a founder reading this, it helps you feel seen. Building a startup is really $%&!ing hard. You’re not alone, and your feelings are valid. Without further ado, here are 8 (completely valid) things that I struggled with as founder - as well as a few tools that helped along the way.
Imposter syndrome - If there is one thing that stands out to me amongst founder friends, especially those who are women, it’s that everyone seems to struggle with imposter syndrome. Something about becoming a founder can send even the most confident individual into a tailspin of self doubt and shame. An important realization for me was to consider why imposter syndrome happens, and help myself to see that the “why” was usually responsible for my feelings of doubt, not my own personal shortcomings. Some common reasons “why” include:
Making “apples to oranges” comparisons:
Startups force you to be a generalist, which can trick you into thinking you have to be an expert at everything. This makes it easy to compare your ability to do any given task to that of someone who is a specialist at that thing.
Comparing yourself to founders / companies who are further along than you.
Comparing your experience to only what you see in the external highlight reel of another founder / company.
Internalizing rejection: Investing is a numbers game and the reality, unfortunately, is that investors will pass on the vast majority of deals they see. It’s usually nothing personal and reflective of preferences and factors that are external to the company, but it doesn’t usually feel that way.
Lack of external validation - the funny thing about being a startup founder is that it is a title you give yourself - nobody promotes you to CEO, gives you permission to be a leader, or writes you a performance review. Lacking the sources of external validation that come with more “traditional” jobs can make it really easy to feel like a fraud.
Rejection fatigue - I can honestly say that I experienced more rejection in three years of buildings companies than the rest of my entire life combined. Unfortunately, it comes with the territory. The average funding round requires 50-100 pitches, most of which result in rejection (or silence.). Many businesses also require founder-led direct sales to get off the ground, which doubles your opportunity for rejection. There are plenty of people out there who claim to be immune to the pain of rejection - to have a “thick skin,” but news flash: fear of rejection isn’t psychological, it’s biological. It’s quite literally hard-wired into our DNA as social animals who need the acceptance of our tribes to survive. Rejection can have compound effects as well. It doesn’t feel good, which results in a desire to avoid the bad feeling, which can result in procrastination and avoidance, which results in shame and a perceived lack of productivity and effectiveness. It’s a vicious cycle.
Physical isolation and loneliness - The days of two buddies starting a company in their garage have been replaced by like-minded people connecting through online forums, fellowships, etc. and teaming up to build something that they are both passionate about from a distance. Resourcing a startup also looks very different than it once did. Traditional full-time hires are being replaced by fractional experts sourced on Upwork and offshore resources that come at a startup-friendly budget. These changes are contributing to Founder loneliness via compounding factors - (1) you usually work alone and from home (2) the job is demanding so you allocate more hours of your day to work than usual (3) capital is scarce, both for you personally and for your business, which results in an inability to self-soothe with an office, $8 lattes, or a vibrant social life.
Burnout - Building a startup requires you to operate in an extremely high-pressure environment for long periods of time. It feels like you’re in a pressure cooker where everyone is counting on you and everything is your problem. When you have so many outside obligations, it’s easy to stop caring for yourself. You work long hours. You reach burnout, and you often don’t believe that you have the option of solving that by resting because of the aforementioned obligations. The feeling that you “can’t stop” can lead Founders to operate while burnt out for long periods of time. Operating in this mode only magnifies other challenges present on this list and can become a difficult cycle to break. The more burnt out you become, the more you shame yourself for not being at your best, and the further you sink.
Cynicism - the large volume of rejection and disappointment that typically comes with building a startup alone can easily bias you towards negativity, but the other culprit of cynicism for me was less obvious - advice fatigue. When you are building a company, everyone wants to give you advice. Pitching an investor is an open invitation for them to critique and provide their two cents on your business. When you pitch 100 investors, you’ll hear 100 different takes on its viability and how you should operate it. The majority of that advice will conflict. Layer in mentors and peers, and heaven forbid you do an accelerator which puts advice on steroids. Too many conflicting inputs make you cynical - you start to believe that nobody knows anything and the system is rigged.
Loss of identity - at best, it can be a struggle to de-couple the identity of your business with your identity as a person (and similarly separating business outcomes from personal outcomes) At worst, you can feel like your identity has been erased and replaced by your business.
Entrapment - The troughs of despair that naturally come with building a business are amplified by the fact that as a Founder, you may feel trapped in the situation. If you hit rock bottom at a traditional job, you know you have the option to leave. Quitting might feel scary or risky, but on some level your brain knows that exiting the situation is possible. Founders generally don’t get the luxury of operating that way - you’ve made a commitment to your investors, employees, co-founders, etc. that is not easily broken. For that reason, the hard things often feel even harder because they are paired with a feeling of entrapment.
Bottling it all up - As a Founder, there were times that I broke down in tears over lunch, but knew I had an investor pitch 30 min later that I had no choice but to get my shit together for. It’s hard to properly acknowledge and process the feelings that naturally emerge throughout a startup journey when you’re moving with the speed and demands of a startup. It’s easy to suppress, bury, and deny the hard things while putting on a strong and confident public image. Putting that kind of pressure on yourself to disguise how you’re really feeling can make you feel completely alone and frankly, like a liar. Showing up in the world as a performed version of yourself instead of the real version disconnects you from yourself. Carrying the weight of the hard things is going to suck either way, but you can at least make it slightly easier by treating the feelings as valid, allowing them to be felt, and being honest about them with others.
Phew, okay - so that section was heavy, albeit honest. Let’s give this post a happy ending by transitioning to solutions. I certainly don’t have all the answers, but have found a few tools throughout the years that had positive impact on my Founder mental health:
Get a mentor - especially if you’re someone who has historically craved the approval and validation of a manager or leadership figure, having a mentor along your journey can be hugely valuable. A mentor can provide a supportive ear to listen, advice on how to navigate the hard parts of building a company, and some of the external validation and cheerleading that you so rarely receive as a founder.
Externalize things with KPIs - you have to find a way to externalize the things that can become very painful if internalized. The hack that I used to do this was to adopt a data-driven approach to sales & fundraising by writing KPIs for myself that I could celebrate. For example, if you assume that you’ll need to pitch 100 investors to raise a round that you want to close in 5 weeks, a good KPI is to pitch (and probably be rejected by) 20 investors per week, bringing you closer to “the one” and generating learning along the way. Re-framed in this way, receiving 20 rejections is a win worth celebrating. Human nature wants to minimize rejection, but a data-driven sales framework seeks to maximize it. This also works because it breaks big things that can feel overwhelming into smaller pieces that provide milestones to celebrate along the way.
Be transparent with your team - at a minimum you have to tell your co-founder or other trusted members of your leadership team how you’re feeling and commit to look our for one another’s wellbeing. Beyond that, however, I found that being transparent and vulnerable with my team usually did more good for the company than harm. Sometimes this looks like saying things like “This is a major decision for the company, and I just don’t feel like I have the clarity of thought to make it right now. Let’s be patient and come back to this when my mindset is right.” Your team will usually respect you all the more for being honest and you get to breathe a sigh of relief because your feelings are out in the open.
Take time off - just do it. You feel like you can’t in the moment, but I can report that startup outcomes are pretty binary. Either they “work” and produce some sort of exit or sustainable outcome for you, or they fail. The chances of the latter are higher (sorry, tough love.) When you get to the end of that journey, you will regret the parts of your life that you put on hold for the startup. The chances that occasional vacation change the binary outcome of your company are extremely slim. You have to find a way to make sure life still happens while building your company - and that includes taking time off.
Say no to anything you want to for any damn reason you want to - Founder intuition is an unexplainable, but unstoppable force. A symbiosis naturally develops between you and your business that you should always pay attention to and honor. You know when it’s healthy and when it’s not, what it needs from you, and what it needs from others better than anyone else. You also know what you need as a person in order to remain the sane and effective leader that your business needs you to be. That means setting whatever boundaries you want shamelessly. When that intuition tells you to say no to something, even if everyone around you thinks you should do it, just say no. Acting against your Founder intuition or spending time on things you don’t believe in will drain your energy at a much faster pace than things you have conviction in. Save your energy and bandwidth for only those things.
Context switch when you need it - give yourself relief from specific tasks when you are at your breaking point with them. It’s not just about the big picture of avoiding burnout and keeping you energy up in the macro sense, there are also smaller ways to optimize what you focus on at various points of time in order to conserve your energy and mental health. Sometimes that means slowing down on one thing and switching your focus to something else temporarily. For me, this meant stopping a fundraising process for a few weeks or a month on multiple occasions and throwing myself back into the joy of operating the business. Doing the “fun part” always helped me get the second wind of energy that I needed to the do the hard part, with the added benefit that the pause often brought strategic clarity on how my pitch needed to evolve.
Build friendships with other founders and tell them the truth - A lot of people only do the first part of this - they have lots of founder friends, but they give each other surface-level updates instead of the whole truth. Even if it’s only a handful of people, you must find the ones that you can really let in - total honesty with someone who authentically understands what you’re going through is the ultimate therapy. While I was temporary living in Orlando to participate in leAD, I went on a walk with two fellow founders and admitted out loud for the very first time that it might be time to shut indiFIT down. I let it all out and vocalized the toll that the business (and its lack of traction) was taking on me. I look back on that conversation, which was met with so much validation and support, as an important moment of clarity in my journey.
Journal / write - speaking as someone who is doing it this very moment, I can assure you that it helps.
