Startup Life – Not What You Think

This is a longer post about working for a startup. For those with the mettle for the job, I highly recommend it; however, if you’re looking for a 9-5, Monday to Friday with ping-pong and bean bag chairs, stick to the cubicle.

Startups are not for everyone.


An example of a typical conversation when I meet someone new:

“What do you do for a living?” asks the person I just met.

“Oh, I work for a startup that focuses on patient engagement in the healthcare field. How about you, what work are you in?” I respond, cordially.

“A startup, wow! That must be exciting! I just work in HR a large company XYZ. But, you, you work for a startup, you must have fun all the time, right?” the new person I don’t really know responds while smiling and digging for their phone so we can swap contact information and they can later ask me to recommend them for a job with a startup.

Inside my being, I die just a little bit each time this scenario plays out. It boils down to the old saying, “Be careful what you wish for”.


Okay, let’s get down to brass tax:

Startups are HARD!

Big surprise, right? Amazingly, due to the romanticism of the Silicon Valley startup scene, people somehow believe that working at a fledgling company is all late night parties, ping-pong, and bean bag chairs. A joyous celebration of collaborative work punctuated only by the exultation of success day after day. Bright sunlight bringing nothing but glory and success to the underdog.

Reality check, television and movies very rarely give you the whole picture – watch them with a grain of salt.

Working for a startup is hard. It takes a certain amount of grit, determination, and masochism to work for a startup. Oddly enough, once you do it once, it gets easier to do it again and again.

When interviewing for my current company (which I love and will continue to full heartedly dedicate myself to until after we achieve “full success”), the CTO (Chief Technology Officer for those unfamiliar with the acronym) asked me, “You’ve worked for one startup, why the hell would you want to go through that again?” My answer was simple, “I enjoy the challenge and don’t mind the workload – every day makes me better even if it comes with a bit of pain” (this is paraphrased, but you get the point).

To work for a startup, you have to be able to endure the pain. Now, pain can come in many different forms, such as:

  • Sleep Deprivation – Weeks, if not months, of 12-18 hour days to deliver work normally performed by 3-4 people before getting a respite of some kind (usually sleeping in for an hour or two).
  • Time away from friends and family – This one has never been too difficult for me (I love you Husband! You know I do!) but can ruin marriages and relationships in short order.
  • Unrealistic expectations – Near impossible deadlines, unrelenting operation’s tempo, and never enough resources to accomplish half of it all.
  • Minimal benefits – Depending on when you start with a start-up, the upstart may not have medical, dental, or vision insurance; definitely no 401k; sometimes a salary is dependent more on the risk you are willing to take than your actual skillset.
  • Never enough time – Speaks for itself.

I think I’ll write a series of separate posts about the myth of work-life balance and what it takes for an average person to be successful at a startup (not merely survive).


ME - ABQ Airport - Oct 2018
Ready to fly out for the 4th week out of the past 5 weeks.

Another old saying goes something like this, “Tomorrow is a better day”.

Guess what? Tomorrow, at a startup, will only be harder than today was and half as hard as the day after tomorrow. It doesn’t get easier until the big VC (Venture Capital) investment or, more likely, acquisition occurs – either can mean the quick end to your tenure with that particular company.

Rare is the day that you walk into the office (open floorpan, of course) or shared workspace or garage and say, “Awesome! I get to take it easy today!” If this is what you’re looking for, seek life elsewhere. Taking an easy day at work is the same as saying, “I feel like putting myself two days behind! Let’s do it!” There is no payoff in taking it easy.


One of the best (and scariest) things about working for a startup is the difficulty of hiding your weaknesses.

In a large corporation, a person can work for 20 years not having done many things. Living as a number in a system; collecting a paycheck every two weeks; always in the right place at the right time to avoid displaying a weakness to his/her coworkers.

Maybe a middle-manager pawns off their presentations on their employees so the employee can take the blame when it is fouled up. Maybe it’s a paperwork shuffle that pins mistakes on an unwitting scapegoat in order to preserve some pension that isn’t likely to survive 10 years. Maybe it’s gross incompetence wrapped up in a sycophant who avoids responsibility through sheer kiss-assery.

In a startup, there aren’t any walls to hide behind. Your coworkers and leadership will see every mistake and every weakness. You can’t hide behind someone else, you have to take responsibility. And in a startup, there is no lengthy HR process to save you – the end is typically abrupt and comes with a handshake.

Now, there is a huge positive in this: you have the opportunity to identify, create a corrective plan, and overcome your weaknesses.

How do you do this? It’s pretty simple: be vulnerable and talk it out with your peers and leadership to develop yourself for the betterment of the company. Of Course, the learning curve is steep and expectations are real so don’t take this opportunity to improve lightly. Dive in and commit to change and you just might make it out the other side.


Would you like to see more posts about startup life in the real-world? Drop a comment below and let me know. Also, feel free to share your startup stories with me on Facebook or Twitter (the links are on the right!).

Expect the worst and hope…you planned enough!

Just about anyone who has met me, worked with me, or is a friend of mine would likely describe me as “negative” or “always pointing out the worst”. To be honest, I won’t deny such claims. I do focus quite a bit on those things that can go wrong and less on the things I hope go right. It’s also accurate to say that I am not quiet about voicing my concerns.

Am I just a pessimist who can’t be happy with any given situation? Do I have this need to shit on other people’s ideas or potential opportunities?

In short, the answer is a resounding “NO” to both those questions. So what’s up with the bad attitude?

I learned a long time ago, before the startup world, before contracting, before the Army, before I moved out of my parent’s house to expect the worst possible outcome and plan to counter any hurdles that can be identified at the start of an idea, change, or action.

The classic saying goes something like this: Hope for the best but expect the worst. Here’s the thing, if you are hoping for the best then you are likely not putting as much effort or thought into the worst. This sets you up for failure before you even start. In the end, you could probably look back and identify multiple issues that arose which could have been headed off from the beginning with better planning.

Tunnel Rat - WEAPONS COMP - oi (4)
Clearing a drainage tunnel with a 9 MM pistol and flashlight – do you think I had a sunny disposition going in?

In the Army, my thought process was reinforced with life and death situations. When you are a leader taking X number of soldiers on a patrol, ambush, or overwatch, you don’t approach the task with a sunny disposition. The default position is along the lines of: “We are going here to do these things and this, that, and everything else is likely to go wrong…this is how we mitigate risk and reduce the threat preemptively”. Sounds pretty grim, right? Well, it is! Real world combat operations aren’t the party Hollywood makes them out to be.

With a few modifications, this mindset is easily translated to the business world. “If we don’t get Update X out by this date then a high probability of losing 50% of our customer base and having to lay off 75% of the workforce exists.” What do you do? Quit? Hang up your hat, have a fancy cold brew, and let it be? HELL NO! You work with the team to make sure the engineers have what they need to produce Update X; you get the team to volunteer additional time in an effort to extend the deadline; you prep your customer base by setting proper expectations; you get to work.

A lot of people accept the concept of quitting. Life was unfair, I quit. My boss was a dick, I quit. The client wasn’t nice, I quit. It’s too hard, I quit. Here’s the problem, you can’t quit life! Life doesn’t care that you are at rock bottom; life isn’t going to stop while you wipe your tears off your face; life isn’t going to apologize for hurting your delicate sensibilities. Life is going to continue kicking your ass until you realize it’s up to you to change it!

Expecting the worst will help set you up for success. Think about it this way: I’m ready for everything up to and including the worst situation possible, anything short of that is easy.

One last thing, try to tackle the worst possibilities with a smile – it always seems to help the people you’ll end up working with throughout your life.

 

How do you handle planning? Do you start with the best possible situation and work your way to the worst? How do you achieve the end goal? Leave your thoughts in the comments below. Don’t forget to like and share on your favorite social media platform. Thanks for reading!