Founder Problems

Founders live some of the most stressful and demanding lives, you have to juggle a million things at once, right? Well this widely accepted trope, is actually a slippery slope. Busy is different than busywork, and too often I find myself and others spending their time on things that don’t really matter, at least at that moment, because we want to feel like we’re doing something. It’s also no secret that founders need focus, but finding that balance is tough, especially on your own, especially in our era of social media, AI and global strife. But what if it was as simple (though not necessarily easy) as just having more structure?

“People think focus means saying yes… It means saying no to the hundred other good ideas.”

-Steve Jobs, WWDC ’97

Yes, ‘structure’ sounds an awful lot like a job... but stay with me. While founders should care about what they are working on and have passion for it in some way or another, balance is still the key.  

In the midst of that precious enthusiasm, many founders end up spinning their wheels, getting lost, burnout or worse. I’ve personally woken up months or years later, scratched my head, and asked - what the heck happened?

While a few founders soar to great heights in “Founder Mode,” as Airbnb’s Brian Chesky articulated in a silicon valley presentation, and Paul Graham of Y-Combinator popularized in his essay... most of us mortals struggle with founder problems. These are less complex organizational management strategies, and moreso personal obstacles that hold us back from even getting to the point of optimizing and sustaining a successful business with a big team and budget.

So we’ve come up with some of common “Founder problems”, in the hopes of holding up a mirror, making you feel less alone, or at least get a good chuckle.  

1. The Morning Ritual of Founder Anxiety

Waking up from anxiety, we often scramble to respond to emails, make product decisions and put out “fires”... which wear you down before you’ve even brushed your teeth. It’s scientifically proven that your first ~30 minutes in the morning set the trajectory of your stress levels for the day, often called “morning spike” or CAR. And Harvard Business Review confirms that stress is a top contributor of burn-out for founders, so maintaining stress management is key to sustainable performance.
 
"Last Tuesday at 6:07 AM, I caught myself juggling Slack, Gmail, and a half‑sipped espresso... an hour later I reached inbox zero, but it took 3 hours until I was able to focus on my actual to-do list."  

2. The Dark & Messy Room of a Founder’s Mind

It’s dark, you can’t see much except vague figures and the general layout... when you try to focus on something you can’t tell what’s exactly real and what’s your mind playing tricks on you. The primitive scattered notes, the growing orphanage of rushed diagrams, and the ghost of a master plan that only a founder can see - are all too common and hard to avoid, as creativity and chaos often go hand in hand for those looking to start their own business.

‍"Master plan? Oh yea... we made one of those last year, let me dig it up."

3. Calendar Bloat... Meetings So You Don’t Feel Empty

Meetings with prospects, advisors, your team, potential partners, etc. become a subconscious need, desperately trying to add structure to your day. If your day is fully booked, maybe you’re doing enough? Or maybe you’re just avoiding the ambiguous, hard, lonely work waiting after the calls end. Atlassian reports that in 2024, more than half of a F500 team’s time is spent in unnecessary meetings... should you or your new business really follow that model?

‍"I reduced my availability for non-urgent meetings to 1 per day, and it has been game-changing."  

4. FOMO, Rushing & The Social‑Media Humblebrag Spiral

Another startup just raised. Someone’s “thrilled to announce”. Your feed is a relentless parade of “humble” celebrations, repetitive advice and nonsensical click-bait. You know not to compare—but founder FOMO is insidious. Maybe you log off quickly, but you find yourself off on some tangent instead of getting your to-do list done. Which of course only leads you to rush through your to-do list at the 11^th hour – as more research is showing, social media is horrible for your mental health.

‍"I made the mistake of opening LinkedIn in the middle of my productive block, now I’m mentally infantilized, just sucking my thumb in the corner yearning for a cushy investment and VC-daddy.”  

5. The Sacred, Never-Ending To-Do List

A founder's to-do list is an especially vulnerable place, usually a more emotionally driven than logical, though I’d never admit that. It's where founders find anxiety, guilt, dread, and maybe solace—but often not for an objective reasons they can explain. Things get done, you call it a day, you throw more tasks on pile for later, and yet deep down you know you’re a victim of your limitations, it’s long been proven that to-do lists are often a deceptive way to procrastinate.

‍"Um what? Why do I have to do XYZ right now?! How dare you question me! You just don’t get it."

6. The Imposter Syndrome Ball & Chain

One day you’re on top of the world; the next, you’re waiting for someone to realize you have no idea what you’re doing. Every win feels accidental, and every setback is a sign the universe is watching you, specifically. Welcome to the tag-team wrestling match with your own self-worth. It’s as amusing as it is tragic to see the ways you maybe hold yourself back from what you say you want, but studies show that being prepared is the best source of confidence (of course, easier said than done).

‍"Just fake it till you make it! (...but what happens when you make it?!)"

7. The Awkwardness of Advice

Everyone has advice: investors, mentors, blog posts, and that one friend who just really wants you to pivot. It’s hard to know where people are coming from, do they have enough context or expertise for us to trust their word? What’s their bias? Suggestions are well-intentioned, but too often leaves you with more doubt about what actually matters - what’s noise and what’s signal?

"I asked my circle for advice and got: “Raise now,” “Don’t raise,” “Bootstrap forever.” ...halp!”

8. The Changing Nature of “Flow State”

Urgent msgs, another random question for ChatGPT, oh your AI agent just finished is latest attempt at something you forgot about... Oh yea there’s a shiny new tool for XYZ... Flow state in the AI era is changing to be more like juggling, and we often confuse productivity for busywork. As a founder you don’t have a clear, cookie-cutter checklist to tick off which AI can help with, and flow often requires deep, ambiguous work. That magical, productive flow state that is the stuff of founder legends seems to be getting harder to grasp... but hey, you pumped out 10 AI-generated blog articles today!

"Our engineer hit flow at 11 PM—because everyone else was asleep."  

9. Calendar Fog Isolates You From Humanity

Without a clear, confident plan you’re at the mercy of busy-work, distractions, and guilt that block you from committing—or even enjoying—a trip your friends are planning for next month or a hike this weekend. Days blur, boundaries dissolve, and your sense of self outside “the company” gets harder to reach... infact, time off is one of the biggest struggles for founders, leading to burnout.  

‍"I RSVP’d “maybe” to my own b-day dinner... because you know, something might happen at work."  

10. But Have You Tried XYZ Tool Yet? (Tool Gluttony)

Don’t you want to 11x your workflow? Look at all the reviews! While using modern tools is useful, there is always a learning curve and there is such a thing as too many – especially as its becoming clear that many tools overlap and redundancy becomes more of a problem. App fatigue is rampant, skills are still king, and you shouldn't need 29+ apps just to keep up. Especially in the AI world, where software is consolidating and how you prompt matters more than what tool you use.

‍“We trialed six 'AI Sales Agents'... Net improvement: My password manager grew its goodie bag."  

Siift Your Business, Prepare for the Long Haul.

It’s no secret that a founder’s biggest enemy is often themselves... so if any of these examples felt familiar, you may want to give siift a try. From decades of banging our own heads against the wall, we’ve now developed a modern AI UX, that bakes in a thoughtful series of mechanisms to help you stay focused while avoiding all of the above, and make steady progress on your business while achieving peace of mind. Try it out for yourself, Founder Mode wasn’t built in a day.