The first 30 days at a startup: What to expect

Disclaimer: I wrote this article about a year ago when I was working at a startup for the first time. I'm not working there anymore. But this was one of the more fun pieces I worked on as part of a "content swap" (even if my boss at the time didn't find it so funny).

What's a content swap, exactly? Well, the folks at Valuer and I essentially guest-blogged for each other in exchange for content (obviously) and the ever-important backlink. I thought I'd share it here for a good Friday laugh!

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You can find tons of hashtags across social media platforms specific to startups and the culture around working for one.

You can even say that startup jobs are all the rage.

But oftentimes it’s hard to figure out what it’s really like working in an organization that’s built from the ground up. The countless articles and lists of pros and cons all over the internet certainly send some mixed messages.

Thus, the startup life has taken on somewhat of a mystical and mythical persona.

Though it’s true that every career path and start to a new job is unique, there are some valid similarities for anyone starting out their first 30 days working for a tech startup.

Be sure to take this week-to-week breakdown with a grain of salt or two. It’s a compilation of experiences across a few tech startups, and all contributors I interviewed shall remain anonymous.

After all, one must balance the humor and reality of it all…

Week One: Honeymoon Phase

Granted, this term “honeymoon phase” is most often applied to matters of love and romance, it’s also applicable to any kind of new relationship including that of you and your new job.

• Day 1 (Monday): It doesn’t get any better than this—the euphoric feeling that you’re working for a cool and super casual startup. You even get a welcome lunch at some fun and trendy place in the neighborhood!
• Day 2: You have yet to receive the iPhone and laptop you were promised, but you really don’t want to bug your co-founders about it. Besides, at least you’ve got a company email address assigned to you so you can sign up for all the apps, platforms, and tools the company uses.
• Day 3: You’re getting up to speed on everything while enjoying the free food and drinks that get magically stocked in the kitchen. Time seems to be flying while you’re at the office!
• Day 4: It turns out that everything you thought you’d be doing once you hit the ground running has been thrown out the window. But it’s fine. You’re up for anything in this startup environment. That's what you said in the interview process, right?
• Day 5: You attempt to knock a few of the smaller things off your to-do list. But your co-founders decide to call it a day at 3 pm and deem it beer time! You truly feel welcomed and could get used to this kind of company culture.
• Day 6: You spend your Saturday basically counting your lucky stars you landed such a fantastic job.
• Day 7: Some of your Sunday is spent researching and prepping for the actual work you’ve got to do the next week.

Week Two: Honeymoon Recovery Phase

We’ve all had that feeling when we need a vacation after our vacation to recover from all the vacationing. Well, it’s the same feeling as you cruise into the second week of your job at a startup.

• Day 8 (Monday): Hopefully you’ve got your phone and computer situation all sorted out. Now you just need to download more apps and tools and make sure you save all 4,284 passwords you created for them.
• Day 9: While you’re on-boarding yourself into all the new software you need to use as a team, you start digging into the more serious projects on your plate. You start to feel very alone with no big team to turn to for brainstorming.
• Day 10: You’ve managed to cross one project off your list. Nobody seems to care but you know it made a difference. The truth is, your co-founders just don’t have the time to pat you on the back for every little thing. Autonomy at work is an actual thing.
• Day 11: You still have a mountain of tasks to complete but at the “team status meeting,” you’re told they all need to wait. Priorities have changed. No problem! You put in extra hours to adjust to the changes.
• Day 12: You discover that priorities have shifted again. Welcome to startup life!
• Day 13: You let yourself sleep in Saturday morning but hate yourself for it because you’ve lost valuable time you could have used to get some work done.
• Day 14: You try to enjoy what’s left of your weekend but your mind is already at work as you think about all the things that piled up on your to-do list during the first week.

Week Three: Reality Starts Setting In

You understand now what it feels like to age in dog years. You’ve been on the job for two weeks yet it feels like it’s been 2 months.

• Day 15 (Monday): Depending on your role, your CEO, CTO, COO, CMO or C—fill-in-the-blank-O will sit you down for your first “check-in.” During this meeting, you’ll be told to forget about your old to-do list because priorities have shifted…again.
• Day 16: You start to wonder if you even deserve the new phone and laptop you’ve received. Your daydreams turn to day-nightmares of getting fired for lack of deliverables.
• Day 17: You’re exhausted from troubled sleep patterns, or lack of sleep altogether because you’ve been burning the midnight oil trying to finish tasks. You desperately want to have something to show for all the hours you’ve spent at your desk.
• Day 18: Your confidence is at an alarming low but then you have a major breakthrough on a project/deal/task and the team cracks a few jokes and throws some backhanded compliments your way. You feel worthy again.
• Day 19: There’s so much stuff to cross of your list but then little fires pop up that need your attention. You spend most of your day doing stuff that isn’t “necessarily” a part of your job.
• Day 20: Your friends don’t take your calls anymore because you’ve declined all their invites to hang out and have a social life like you used to.
• Day 21: You do a chunk of work and feel really productive after knocking a few things off your to-do list. You’re so ready for the new work week.

Week Four: The Honeymoon Is Definitely Over

All good things must come to an end. The honeymoon might be over but you definitely don’t want a divorce.

• Day 22 (Monday): You get called in for another check-in meeting and you’re asked how much progress you’ve made on your workload from before-before the changing of priorities. You leave the meeting feeling like a major underachiever.
• Day 23: You truly start to believe that you don’t even deserve a job. You feel hopeless that you’ll ever deliver your work fast enough. You forego the free lunches and punish yourself by eating crackers at your desk while you work.
• Day 24: You notice your clothes are feeling a little tighter while sitting behind multiple computer screens day in and day out.
• Day 25: You juggle 79 things at once and then get the news that the team is getting an intern starting on Monday. You feel relieved that there will be another helping hand around.
• Day 26: You ask one of your co-founders if maybe the new intern can take a couple of things off your plate and you receive a friendly but firm NO.
• Day 27: You attempt to do the 6 loads of laundry that have been piling up in your house, but you give it up at 2. Fresh underwear and towels are all you really care about.
• Day 28: Your stomach is upset the latter half of Sunday thinking about the inevitable sit-down that will happen the next morning.

Week Five: You’ve Survived Your First Month In

• Day 29: The routine check-in meeting turns into a team status meeting welcoming the new intern. During said meeting, all your co-founders introduce you to the newbie and praise your work and work ethic thus far. You sit there shocked.
• Day 30: Your self-esteem is up a few notches. You’re working for a cool and super casual startup. You even take the new intern out for a welcome lunch at some fun and trendy place in the neighborhood!

The Moral Of The Story: Ifs and Thens

This 30-day take is part-reality and part-joke. Employees and founders alike can attest to this.

The startup life isn’t for everyone, and it’s a sink-or-swim culture whether or not anyone admits it. So you should weigh your options when job hunting.

Here are some ifs and thens to put things into perspective:

In the short term you may flounder, but always keep your eye on the horizon for your long-term goals...

1. If you don’t want to work outside of the 9-to-5, then you shouldn’t seek work in startups.

2. If you can’t juggle juggling and then juggle some more, then don’t even think about working for a startup company.

3. If you need hand-holding by way of a mentor or a manual then you’d best end your startup job search now.

4. If an impending onslaught of new apps and software platforms makes you anxious and insecure, then working at a tech startup is probably a bad idea, to begin with.

5. If the thought of complete autonomy at work brings on a panic attack, then steer clear of roles in startups.

6. If you need a black and white separation of personal and professional life then working for a very small company such as a SaaS startup, or any startup for that matter, is not for you.

7. If you need to be reminded to meet your goals, then you’ve already failed.

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Originally published at https://valuer.ai/blog on October 25, 2018.