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!).

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