Imagination and Practicality

jeff gorvette carWatching my two kids play, it’s striking how different they are. My younger son (4) turns everything into a make-believe game. Give him two sticks and suddenly they’re space ships. Give him a handmade car (which we built recently at the Halifax Art Gallery; it’s meant to be Jeff Gorvette from Cars 2) and he’s doing a race through the hallways of the place for an hour. His imagination is incredible.

My older son (7) has a great imagination as well, but he’s also much more practical and analytical. It makes sense because he’s older, but he’s always been that way. Give him two sticks and they’re two sticks; he may want to see how far he can throw them or whack them against a tree to see them break … but they’re still two sticks. If someone suggests to him that they’re lightsabers and we should battle as Luke Skywalker and Darth Vader, he’ll absolutely join in and participate … but he’s not creating fantasy worlds around himself. His practicality and analytical approach to things helps him solve puzzles, ask insightful questions, and stick with things that need resolving.

It seems to me that startup founders need a healthy dose and mixture of both imagination and practicality. One without the other makes you an incomplete founder and leader.

I think it’s possible to work on and train both your imagination and analytical skills. There are hobbies for example, that help with both. Take photography. It’s creative and imaginative, but requires a keen eye, technical know-how (if you get past basic cameras), and good timing. Drawing is another good example. On a personal level, I’m hoping to work on both photography and drawing this year. I’d like to take more pictures and learn how to take better ones. That’s part of the reason I’ve put my Instagram stream at the top of the blog; to remind and inspire me to keep taking pictures.

There are lots of ways that you can push yourself to be more imaginative and more practical at the same time. And that balance will help you be a more successful startup founder and leader.


Sleeping Under Your Desk

sleeping under desk

I’ve slept under my desk before.

A few times in fact. It wasn’t comfortable, but it was more comfortable than sleeping on my chair or on top of my desk (I’ve tried both.) Somehow the existence of the desk made it feel a bit safer…

At one point (at one of my startups many years ago) we bought a couch that converted into a bed. I never used it, but my partner did. Others may have as well. There was an air mattress floating around somewhere too.

Startups aren’t fair. Neither is life. It may be that entrepreneurs are so young these days (particularly in the hotbed of Silicon Valley) that they haven’t had enough life experience to appreciate that fact. They’ve got all the enthusiasm and hustle in the world (both needed in massive quantities to succeed) but not the battle scars to understand what it’ll ultimately take.

But startups don’t own the “work insane hours like mad fools” space entirely unto themselves. Have you ever met a doctor that’s on a 24 or 36-hour shift? Now that’s insane, especially since they’re job is to save people’s lives. I’ve known young lawyers who join a firm as a junior associate and work absurd amounts; consistently more, for longer periods of time, than most people in any startup. And big game companies are known for pushing their people into super intense crunch periods before their games are finished. Life is hard. Work is hard. No shit.

There are plenty of examples of people having to work hard. Perhaps too hard. There’s definitely a startup culture around working tons of hours, although you can’t measure success or output simply in hours. Most of the time there’s some level of compensation: high salaries, big bonuses, etc. Whether the compensation matches the expectations is not always obvious or true, but there’s usually something in place. In a startup, the motivation is the experience – you either want to live the experience of the roller coaster or you don’t. I completely understand if you don’t, and even those addicted to the experience question themselves from time to time when things are really bad. Compensation in startups is tricky because salaries are usually lower (certainly at the beginning) than market value. This is often compensated with equity and the dream of future riches. Most don’t get there, which is why those future riches are a difficult lever for motivation, especially when the equity doled out is so little. The earliest employees deserve a bigger piece of the pie.

There are lots of great reasons to join a startup. But there are cons too. That’s life – pros and cons – and being able to balance those to your own comfort level is important for your survival and success. I don’t see the level of complaining that Michael Arrington makes reference to, but it doesn’t surprise me. The grass is always greener on the other side right?

Whenever this discussion around work/life balance, startup culture, startup “realities”, etc. emerges I always go back to a post I wrote in July, 2007 when I was starting Standout Jobs and my second son had just been born: How to Start a Company and Family at the Same Time. It still makes me nod and smile, and although my kids are a bit older now, it’s still a crazy struggle every day to figure out the right balance between family, startup / job, myself, my wife and life. Who knows if I’ve got it right?

Joining a startup – particularly an early stage one – isn’t a simple career choice, it’s a lifestyle choice. You have to go in eyes open and not only understand what’s coming, or just appreciate what’s coming, but embrace the experience fully, and be in it because of the experience.

And every once in awhile, that’ll mean sleeping under your desk…

Man lying under desk image from Shutterstock.


Startup Founders Need to Constantly and Instantly Jump from Vision to Detail (and back again)

Some people spend all of their time in the clouds, thinking big thoughts, dreaming big dreams. They’ve got a vision for something and they can (often eloquently) speak to that vision and why it should be a reality. They’re “big thinkers.” Some people are completely the opposite – so detailed-oriented that they have to inspect everything, control everything, and make every decision from the most important to the totally mundane. Let’s call them “perfectionists.”

Most people are in the middle.

I think startup founders need the ability to instantly and constantly move between the two extremes. The middle isn’t good enough. Neither is remaining with one of the extremes, because you’ll either be incapable of making things actually happen (as a visionary) or you’ll be too slow to build momentum and remain competitive (as a perfectionist.)

Startup founders need vision. I’ve called it a big, honest vision. It’s audacious and grand, but at the same time not delusional and absurd. Founders need to picture a world where their startup is insanely successful and having an impact. And they need to share that vision in a big way with their team. But without an ability to execute – without an ability to get into the dirt, identify the nitty gritty that requires attention, and fix real, every day problems – nothing gets done. You have to be a master of getting things done, efficiently, decisively and aggressively.

From a 30,000 foot view to a 3 inch view, founders need to swing back and forth at any given moment, and be capable of excelling in both worlds. They have to be able to tie the worlds together — understanding and communicating (to their team, investors, customers, partners, etc.) why making what would appear to be minor changes or decisions is part of a bigger, visionary plan, and how an audacious vision can be achieved through focused attention on details and execution.


About Ben Yoskovitz
I recently joined GoInstant as VP Product. GoInstant changes how we use the web, making it shareable like never before.

I'm also a Founding Partner at Year One Labs, an early stage accelerator in Montreal. Previously I founded Standout Jobs (and sold it). I'm a hands-on startup guy, helping companies grow successfully from the idea forward. You can reach me at byosko at gmail dot com.

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The opinions and commentary on this site are mine and mine alone. They do not necessarily reflect the opinions or positions of my employer, GoInstant.