6 Ways to Avoid the Mental and Emotional Costs of Being a Startup Founder
Updated: Sep 1
Startups are hard.
Really hard — mentally and emotionally.
Where there is a challenge, there’s prime real estate to learn valuable (and often hard) lessons.
Startup founders face many commonalities: from figuring out how to grow the business while managing day-to-day operations and team members all the way up to deciding if and when to sell.
Can we learn from their shared experiences and avoid those mental and emotional costs?
You can bring immediate awareness of what you’re doing and how that may affect your business in the long run with these six helpful pointers.
1. Things always take longer than you think
Predicting time is the one skill that everyone seems to struggle with.
From underestimating how long a simple task of writing a “quick” email takes, to overestimating your abilities and completing it in a timely manner, or forgetting about all those tasks you wanted to get done this week — we’re terrible with predicting time.
Who’s not guilty of underestimating their timeline for an upcoming project (just look up a couple of early iterations of famous startups’ slides…)?
I bet if someone asks you when they can expect the next update on something, you tell them two days instead of three because “two” sounds so much better than “three.”
How’s that working out?
Testing, branding, content, newsletters, tech, sales, verticals… always on the outstanding list, never changing status on your Gantt chart?
Predicting how long things take is near impossible, but what isn’t impossible is managing the gap in expectations.
You can start being more proactive, think ahead, and account for unexpected things to happen.
Instead of hiring someone “right now”, you need to build a quarterly hiring plan that feeds into the yearly goals. This, of course, is only possible if you’ve done something a few times and you can draw your lessons from it.
If you haven’t, then at least allow for the learning curve.
2. The sure way to crush the business is a mis-hire
It’s catastrophic. Hire the wrong person, especially for a senior role, and it can even kill a startup.
The sooner you realize how important hiring is, or how hard it is to know if the hire works out or not, the more you’ll avoid running in place on the treadmill when you make a bad hire.
Mis-hiring is detrimental.
First, it’s bad for progress.
If you hire someone who doesn’t have the right experience, everything will take them longer because they’re doing it for the first time.
If they’re not in line with your work ethic and commitment, everything will take longer.
To grow as an entrepreneur and stay on timelines, you need to get better at being proactive around when to hire. That in itself assumes you know what you’re doing and all your hires are exceptional, working at the pace and quality you expect.
Make the wrong hire, your timeline breaks down and the business moves forward way slower than you want it to.
Meanwhile, your mis-hire gets more senior and their direction setting and actions guide the actions of others. If they have a relaxed attitude to strategy or hire, they can easily hinder the progress of the entire part of the organization they lead.
The impact on progress is undeniable.
There’s also the impact on culture. If the mis-hire is not a good cultural fit, people in the organization will not enjoy spending time with them several hours a day. If the mis-hire isn’t a good skill-fit, people will question their abilities constantly…
… and yours as a hiring manager for bringing someone like that on board.
You know. People wondering, “What were you even thinking when you brought that person in…?”
By the time you realize they’re a bad hire, others around them who spend way more time under their management would have had their doubts for some time.
A no-win scenario is taxing on your founder’s psyche. It takes time to realize someone isn’t a good fit and you can’t fire them the next day.
Here’s how it’s a slow and painful grind.
First, you wait for them to get up to speed before seeing early glimpses of concern. You brush those concerns aside at first; the person’s new and they’re learning, after all.
In three to four months it’s clear they’re not a good fit, but you can’t fire them. You put them on a performance improvement plan, provide feedback and try to turn a corner.
Sometimes they do. More often, they don’t.
Six months in, it’s still not working and you need to have that conversation and let them go.
Even if you’ve done this a dozen times, it’s taxing. You vacillate between dreading the business moves slowly because they’re not the right fit and dreading the hard conversations.
Take hiring as seriously as you humanly can.
3. Set expectations
It makes or breaks an employee’s experience at your company.
It’s uber important to realize expectation setting happens all the time even without even paying attention to it.
During the interviews, candidates want to know about the culture at your company. You give an answer to that question — you set an expectation.
When you address your employees at a company event or in a monthly newsletter and talk about the next year and where you’re going — you set an expectation.
You hand over a job description to a candidate or talk to your employee about their trajectory and when they’ll be up for a promotion — you set an expectation.
It’s easy to do and there’s no immediate impact, but the long-term ramifications can be brutal. People leave companies all the time because expectations weren’t set properly.
This is an especially common problem for startups and first-time founders. First-timers want to make sure they’re the best managers ever. One way they think they can do this is by making lofty promises about promotions and compensations that aren’t realistic.
“Sure, we can talk about that 10% rise next year. My door’s always open.”
If you’re a first-time manager, or you’ve hired and promoted someone to a first-time manager, just keep an eye on them because they’re most at risk of improperly setting expectations.
4. Very few decisions are right or wrong
Most of your existence as a professional sits in a murky middle. The way to thrive there is not by arguing what is right or wrong.
It’s considering what the trade-off or opportunity cost of every decision that you make is.
Suppose you want to launch a paid offering, such as a course. Like most decisions, arguments can be made for why you should or shouldn’t have built this product.
The “should side” would say your platform already serves as a great place to educate professionals, and a course would further that goal and diversify revenue. It could be an interesting wedge into building out a portfolio of products.
The “shouldn’t side” would say your core business is crushing it, and you should triple down on that. Courses might be a distraction, plus it’s done to death with all that competition out there in the world of online education.
There might be good arguments for both. The way you make this decision, and most decisions in the business, is by understanding the opportunity cost of whichever path you choose.
Turning your default brain to an auditor of trade-offs versus right or wrong is an important change of mindset.
5. Quickly learn what you’re exceptional at and outsource everything else
You’re most likely to be great at one or two things. For other things, the likelihood is that there’ll be someone better who can do those things for you.
Say you’re great at thinking creatively and storytelling. For other stuff, there is someone better. Find ways to take yourself away from the things that aren’t creative thinking and storytelling.
You can focus on content marketing and sales while you let someone else focus on finance, tech, or growth.
Few years down the road that’ll mean you’ll be spending your time on new product development, sales, creating content, or hiring people.
If you’re competitive by nature, you’ll find letting go of things you’re not best at challenging. But know that you can’t be great at everything. It’s not efficient and it’s not what’s best for your business.
Once you let that resistance go, you’ll provide the space needed to hire talented people into positions that aren’t your zone of genius.
6. Curiosity is a founder’s guiding light
What’s common amongst successful people besides perseverance?
It’s not being highly educated.
It’s not even working 24x7.
It keeps their brain working so they don’t get complacent when business is doing well. It allows them to adapt. It leads to serendipity, like getting passionate about a new idea, finding a new business opportunity for their existing business, or meeting someone valuable to add to their network.
It also leads to being a deep generalist, which is a tremendous asset for a builder.
Business studies have long encouraged specialization over generalization. But the more time you spend in entrepreneurship, the more you’ll see that becoming well versed in many things, is more valuable than being an expert in one thing.
Take Patrick Collison, the CEO of Stripe. Patrick, 32, originally from Ireland, runs a $95 billion payments company.
Patrick is a software guy at heart, that’s his first love.
But his range is impressive; he’s exceptional at speaking deeply about many contexts. In his recent interview with Ben Thompson, he went deep into talking about the history of private companies acting neutral and apolitical. He referenced the Progressive Era in the 1900s. In another interview he did, he talked about his excitement for biology and understanding RNA and neurons at a deeper level.
Like all successful founders, he’s extremely successful because he’s curious, he loves going deep in a variety of subjects, and then finds connections between seemingly disconnected topics.
Learn from the founders who’d been there and done that. Look for their playbooks and study them line by line. Sure, good things will come to those who wait… but why do that when you can go and get them yourself at your pace?