There are certain mindsets every founder has to actively work to avoid, like pressuring yourself to personally touch every project, believing you have to be “killing it” at all times when you’re talking about your company to others, and feeling like you can never rest. I’ve personally made all 3 of these mistakes (and every other mistake you’ll see here), and each one can really take its toll.
Looking back, it’s easy to say I shouldn’t have made these mistakes, but when you are in the thick of it all, it’s all too easy to fall into one of these traps.
Here are five of the most dangerous mental traps I’ve fallen into — so learn from them!
1. Saying, “I’ll just do it,” if you see a teammate moving too slowly and you feel like you can do the work faster yourself.
This is the mistake I find myself making most often.
It’s especially prevalent among founders of early-stage startups, in those situations when you’ve hired a new team member to take over some part of your job for you. The truth is, a new hire will need time to ramp up, to learn the job — and of course, during that learning period, they won’t be able to complete the tasks you used to do as fast as you can.
But that doesn’t matter. Taking over their workload is the opposite of what you want to do, because it will prevent them from ever being able to run their domain autonomously. That will, in turn, prevent you from ever being able to scale your company.
And it’ll have other side effects, too. Stepping on your new teammate’s toes damages their morale — especially if they’re already suffering from a bit of Imposter Syndrome. And it wastes money in opportunity cost, mostly in the long run.
Let your new hires struggle so they grow — at least for the first few weeks.
2. Measuring hours, not progress
In the startup world, it’s annoyingly common to overhear people bragging about how often they get to the office early or stay there late.
That literally means nothing.
Unlike in Corporate America, that facetime doesn’t matter here. All that matters is progress.
Here’s what I’ve learned: I would rather have my team sleep later and leave earlier if that means they are sharper and more productive when they’re in the office. What matters are deliverables. To measure someone’s contribution to a growing company or cause, you need only look at things like:
- What they accomplish
- If they hit roadmap goals or deadlines
- If they’re a reliable and respected team member
Of course, founders often behave in ways which prop up this fallacy, too. I try and avoid doing that by creating daily checklists for myself, and measuring my day in accordance with what manageable tasks I’ve accomplished or made progress on during the day.
Ultimately, being goal-oriented — as opposed to hours-oriented — is how you align conceptions of “productivity” with success, for both yourself and your team.
3. Feeling like you can’t take a break
Many founders routinely push themselves to the point of exhaustion in running their company — mentally sprinting 18 straight hours a day, never allowing themselves to stop, sleep, or take a vacation. They feel it’s what they need to do. I’ve even seen founders post about their “work ethic” on Instagram or Twitter as a way to get some social validation that what they are doing is “extra-ordinary”. Nothing gives you motivation these days like that late night “like” or “retweet.”
But in reality, that’s unproductive. Burning yourself out makes you less effective. The startup life is a marathon — not a sprint. And despite some of the very strange and very brilliant people you’ll meet along the way, we aren’t all robots (or cyborgs)…yet.
If you find yourself constantly inundated with tasks or action items that seem to force you to work without ever taking a break, take a step back and reflect. Often, you’ll find that you’re taking longer than you likely need completing certain tasks because you are:
- Distracted (not all emails need to be answered right away)
- Mismanaging your time
- Not giving yourself enough “deep work” time
It’s about being purposeful. The old adage really does ring true: work smarter, not harder.
That also means allowing yourself to take breaks.
4. Trying to be the “cool boss”
There’s a fine line between being the “boss” and being a friend. When you’re running an early-stage startup — beholden to your team, investors, and to yourself — it’s always better to be the former.
That means, essentially, being (painfully) honest in your constructive criticism and coaching.
It’s good to be friendly, but feigning honesty will have drastic consequences, both personally and company-wide. Among other things, it will:
- Promote an overtly political company atmosphere in which your team is competing not to be productive or valuable, but to be a member of some founder “inner circle.”
- Eat away at you personally, since the problems you fail to call out are never being remedied. This will eventually cause you to resent that person to the point of wanting to fire them.
- Cripple your product, since the feedback loop is broken.
- Prevent your company culture from growing into one of honesty, transparency and constant feedback, which is what you need.
- When you need to have hard conversations, just rip the band-aid off. Be direct and say what you need to say. It’s the only way things will improve. And, truly, as long as you remain professional with your feedback, nobody will fault you.
The truth is, your team will — and should — fault you if you’re not doing your job.
5. Thinking you need to tell everybody things are going great all the time
Founders might be more guilty of this mental trap than any of the others. Talk to a friend or colleague who’s starting a company right now, and ask them how it’s going. 99% of the time, you’ll hear: “It’s going great.”
Not only is this often dishonest, but it has other unforeseen consequences, too. It can:
- Piss people off, since most of the time it comes off as disingenuous or as you stroking your own ego.
- Preclude you from receiving what might be very valuable advice or help, since those who could give it to you won’t think you need it.
- Decrease your credibility — especially after people find out things actually aren’t going great, even though you told them the opposite just a short while ago.
- Personally, I push myself — at this stage in my career — to be completely honest when answering this question. “You know what?
- Sh-t’s hard right now.” Saying that to people at the very least is honest, and better yet, might help me form bonds with others who’ve gone through the same struggle.
At the end of the day, everyone involved in the startup grind makes mistakes.
That’s to be expected. What’s important is that you don’t make the mistakes you can avoid.
That starts with avoiding these mental traps.