Are You Right For a Startup?
Several years ago, I joined a startup. I will never forget my first day.
I walked into a building on Market Street in the Financial District of San Francisco. I figured the front desk would know where to direct me, but my name wasn’t on the “list.” I called my new boss, told him I needed access to walk in so he made a call and they let me up. I got to the front desk of my new company and waited in the lobby for about 25 minutes before my new boss rushed by me wearing a soccer jersey, gym shorts, and tennis shoes. Luckily, we made eye contact because he was heading downstairs for a nice morning jog. He grabbed me, took me inside, handed me a laptop and said, “make some calls.”
Welcome to the startup life
As one of the first 50 employees, I’ve been fortunate to see the company grow to well over 1,000 employees. We have a joke internally where we compare startup years to dog years; one year at a startup is seven years at a developed company. It truly feels that way though. Over the years I’ve seen dozens of all-star hires come through our doors, only to stick around for a few months and move on to the next adventure. Make no mistake, working at a startup is a grind and it’s not for everyone.
So how do you know if a startup is right for you?
There are several questions you have to ask yourself before jumping into a startup. After several years, I’ve dwindled these down to 6 questions I ask before hiring someone:
1. Do you need instructions?
Do you read the instructions? If you’re used to being instructed step-by-step, a startup is not for you. Guess what? There are no instructions at a startup. It’s a major culture shock, especially coming from a well-established company. The processes you’re used to, they’re not there. There is no here’s what you do when “X” happens. Most of the “processes” are Band-Aid approaches that work just enough to keep business moving.
On the other hand, if you’re the person who tears through the box and puts things together as you go, a startup is for you. If you enjoy fixing things, chances are you’ll do well at a startup. There’s a lot to fix… to succeed it’s on you to not only figure out steps to take when a new scenario presents itself, but also document these steps. That way your successors know what to do when they encounter it (this is a great way to gain credibility too). Then they can take that process, tweak it, and improve it. That’s how processes are made.
2. Do you seek problems or solutions?
This one is huge — and it’s important to be honest with yourself here. Some of us are great at finding problems, and that is an excellent characteristic to have.. in certain professions. Like in the legal field, working for a publication or as a home inspector (imagine a home inspector who sucked at finding problems).
When it comes to a startup though, that’s not enough. You have to think ahead of the problem and come with a solution. Everyone knows there’s a problem, but they have stopped there. In order to progress at a startup, you have to think of the solution and think outside of the box. That’s the beauty of working for startups — your two cents matter. If you’re okay with problems and taking the extra step to find solutions, you’re bound to do well at a startup.
3. Are you okay with rejection?
This could say, “do you enjoy challenges?” but that sounds a little too easy. One of the toughest parts about working at a startup is the constant rejection. Externally, no one knows who you are. If you’re working with other businesses, they’ve probably never heard of you. Get used to being hung up on, not getting email responses, and plenty of dry spells. Internally, you get rejected daily because your proposals don’t fit within the budget or we’re not at that stage yet. Get used to rejection. Not only will you have to find solutions to the problems your company faces, but you will also have to sell anyone and everyone on why your proposal makes sense (or cents). If you take rejection personally, a startup is not for you.
Side note: this doesn’t say, “do you enjoy rejection.” You don’t have to love rejection to work at a startup. Anyone that tells you they do is lying. I still hate being rejected, and I’ve worked in sales for nearly ten years. The key difference here is that working at a startup has given me thicker skin. It’s taught me that just because it’s a no for now, it’s not no forever. It’s shown me to see rejection in a different light — one step closer to acceptance.
4. Do you handle change well?
This is probably the biggest indicator of how successful you will be at a startup. Can you handle curveballs? Do you get derailed when things don’t go your way? Do you need to plan out your day and stick to a schedule? If so, the startup life is not for you.
Working at a startup makes it nearly impossible to stick to a schedule. I’ll give you a quick example, just today I was training 19 new hires (in a room made for 12 people). Within the first hour, the TV stopped working so I couldn’t project on the screen, two employees tried to kick us out of the conference room we were in because they had it reserved and 6/19 new hires could not log in to their desktops.
What did I do? I grabbed a projector from a different suite, I found the two employees a different conference room, and had the six new hires log in to different desktops so they could get their work done while IT came down to fix their issues.
If you’re someone who would allow these curveballs to derail your day, you’re probably better suited passing on a startup.
5. Do you want to work 40 hours a week?
Are you signing up for a 40-hour workweek? I have news for you, if any startup tells you you’ll be working 40 hours a week, just move on. You’ll be lucky if you leave the office after 50 hours. The first couple of years at a startup are a grind. There is always work to be done, but at a startup, this rings even truer. What’s worse is you look around and this is the norm! This can be exhausting if you’re not bought into the company vision. If you have obligations outside of work, like kids to take care of or side hustles, a startup may not be for you.
On the other hand, if you are someone who gets “lost” in their work, this can be a huge pro. There’s something about charging through those first couples of months/years that really builds team comradery. You’ve been through the struggle together and can bond over the “good old days.” If you don’t mind burning the midnight oil for something bigger than yourself, a startup may be for you.
However, be careful not to accept a 50+ hour work week as the norm. In the beginning, the grind of a long work week is normal because the processes to improve are abundant. During this stage in the startup, it is important to be intentional with work-life balance. Working overtime because you’re passionate about your work is one thing but make sure you don’t burnout. I have a few tips on managing burnout here: How I Survived Burning Out.
Bottom line
It may sound like working for a startup is all pain and no gain. You work long hours, you’re compensated less than you should be, you lack job security and any sense of organization. However, the fulfillment felt watching a company grow because of your blood, sweat, and tears make it all worth it. I can honestly say I wouldn’t be in the position I am in now with the responsibility I have now had I stayed at a well-established company.
