🫠 How I’m navigating energy dips and tough times as a repeat entrepreneur

What I wish someone told me years ago

Let’s start by imagining the following

• You have everything you’ve ever needed to live comfortably — enough savings, a support system, a loving partner, a family, a safe home

• You’re also working on stuff you’re actively choosing to work on — 100% aligned with your goals/motivations and areas of growth — you’re not working for money. You can even easily stop working for a while if you would choose to

• Yet you’re constantly finding yourself overwhelmed in the pursuit of lost energy because of responsibilities overload and the sheer amount of things you’re expecting from yourself

Welcome to being an entrepreneur:

This is obviously not a secret to anyone reading this (most of you are or have been entrepreneurs at some point — startup founders, investors, etc).

💡 Things aren’t that different for repeat (2nd/3rd/4th+ time) founders btw — if anything, this swing sometimes makes it even worse because of the added amount of social pressure you feel from others/put on yourself.

In the last month or so, I’ve found myself getting down on energy — and that’s not a coincidence as it corresponded with me starting a new work project (Socap.ai — which we socially launched about a month ago) while having a bunch of other things I wanted to do.

I started digging into that, resuming the regular therapy sessions I’ve stopped for a while, and have made interesting discoveries, sharing my observations in this post and hoping that it would be useful for some of you. This isn’t one of these “I’m so fucking cool” posts — because in reality life isn’t and I have made the decision to start embracing vulnerability more vs mindless grind.

What’s weighing you down?

The first step to changing anything is being aware of what you want to change. I’m the guy who has always felt these things with a bit of a delay.

In fact, I know the following things about myself:

• I’m very likely to get A LOT MORE on my plate than I can actually effectively handle in the long term. I can do a very good job on these in the short term, but whenever this catches up, it’s a tough time

• Following the last point, once my energy level/ability to execute decreases, I start accumulating more and more to-dos I’m not able to deal with at the moment. When there aren’t many of these, it’s fine, but…

• …whenever the accumulation reaches a solid amount, I find it very hard to deal with it in parts/chunks, instead trying to “do everything at once” — constantly procrastinating these things because they’re almost always related to some negative feelings/fears and of course, I don’t want to deal with all of that multiple times — how on earth my gentle ego will be handling that?!

• A good example of the above is “comms” tasks — e.g. before today my LinkedIn, Twitter, and Facebook were completely wrecked with a ton of unsorted requests/unanswered DMs and, most importantly, were blocking me from continuing to actively post there (or anywhere else, actually, because I have this stupid ass perfectionism where posting is a whole system across the board)

What do these things tell you about yourself?

Dissecting this context a little bit deeper and reflecting upon it, I’ve decided to summarize it in the following way:

1. I’m very bad at saying no to things/politely refusing — and prefer to “ignore” something instead of “dealing with it at the moment”

2. Once I accumulate a certain amount of things to do (paired with negative feelings) — I spend a lot of energy on forcing myself to deal with that and feeling guilty in the process

3. I love creating “images” of how people see me/react to me in my own head — instead of focusing on facing the reality

4. I have very high expectations of myself (and am comparing myself to others subconsciously) — and absolutely love critiquing myself in the background (not actively, I’m visualizing this poor guy as the Kreacher elf from Harry Potter)

5. How I see myself from the emotional point of view is not always how others see me — mostly projecting the “I have it figured out” image which has both pluses and minuses and it not very flexible

At this point I would make a bold assumption — for a lot of you, the internal bulb inside your brain must already be going crazy, reacting to a lot (or at least some) of this stuff. I know I’m not alone in this and in fact have talked to dozens of entrepreneurs who were/are going through something similar, no matter how senior/successful they are.

All I wanna say now — that’s alright and I empathize with you. I don’t like using the word “normal” because for me it’s about the word “norm” — and I don’t want these things to be the norm! In fact, I want to find a way to have less than 10% of the impact in a few years time.

🚨 Places like LinkedIn/Twitter normalize success and the grinding culture, just like Instagram normalizes the showing-off culture. As an entrepreneur, you feel like you’re always the last of the pack — this guy has 15 meetings a day, this gal has just gone viral with his post, these guys have just raised $10M seed at $100M post or exited their company.

How to turn the tables and start dealing with that

Whenever things start to get challenging, you start doubting yourself — am I as good as these guys I’m constantly seeing/hearing about? How do I deal with that?

The only way out is through — you need to go into these thoughts and look at what’s bringing you the anxiety.

Here’s my current approach:

1. You need to start by making it very clear to yourself that you’re working on the things/towards things you really WANT TO. Stuff breaks when you actually don’t — and if your goals are external/not really true to yourself etc.

Simply sit down and think through this question for at least 30 minutes. Don’t give in to the usual “yeah yeah of course what I’m currently working on is a good fit” — it actually might be not and it’s tough to admit but crucial before you do anything else.

I’ll give you a glimpse into how I think about that for myself:

🙋‍♂️ Why am I working on Socap.ai? Because I love interacting with the tech startup folks (founders/investors) and see a clear gap in terms of a fundraising-oriented community, plus I’m freaking tired of seeing people using their network to only 3% capacity, instead focusing on spammy cold outreach. GenAI capabilities are finally at the point where we can start experimenting with radically changing all of that but it would require years to build an amazing product, so I want to focus on constant experimentation/sustainable growth.

2. Once you’ve reflected on the things that are weighing you down, you gotta adopt the mentality of “cleansing” — just reserving the time (half-a-day/day, more if needed) to go through everything and:

1. Deal with first-priority things

2. Schedule second-priority things

3. Refuse/remove the action items from third-priority things (this is key!)

The key here is to basically default all of the accumulation you did before. And the only way to do this is to acknowledge that this is what you need to do, really feel these fears, and dig through them.

Once you do this, you’ll feel that much lighter. Believe me.

3. What can you change in how you do stuff in order not to allow yourself to accumulate stuff like that? What can you change in what brings you more weight overall?

How can you change the approach to judging yourself?

This is very subjective but for me, it’s all about focus/awareness at any given morning. I’ve already written at length about my productivity practices so feel free to look there if you want to.

4. Normalize feeling down every once in a while.

It’s not only you. As I mentioned before, Twitter/LinkedIn is always about the good stuff — launches, demos, etc. No one posts when they’re down, but they are. The key here is to focus on building a great support system — and not being afraid to show vulnerability to your friends/family/coworkers. What I have learned is that sometimes people are much more eager to help you when you’re asking for help vs when they see that you’re “a rock that is 100% in control of everything”.

I’m a big believer that we always have time. But the truth is — not always have the energy. Sometimes it’s ok to say that you don’t have the energy to do these 5 calls and instead, you need a refresher in the form of a football match/sauna (as it is in my case). It’s healthy to take breaks when needed and focus on your personal stuff — there’s absolutely no need to grind 24/7.

🧘‍♂️ The greatest thing about being an entrepreneur is that you control your own narrative. This is something that resonated with me a lot when chatting with Dan Siroker at one of the private events organized by the Rebel Fund (Socap.ai investors). There was a very costly realization Dan has shared — that has almost cost him his previous company — Optimizely: “Whatever you don’t like — don’t just give in to that — you have all the ability to change it, even if it’s 180 degrees. At least try — it’s always in your hands”.

What’s next?

I know you’ve got it — feel free to reach out to me if you need support. I don’t promise to be quick to respond/help, but I will surely come back and stop accumulating things like that.