How To Survive Working At A Startup

Are you a new founder or employee of a startup company? Here’s some gained as Employee Number One in a startup, and some observations of the dynamics of work you will experience in one.

Today is the two-year anniversary of my job at a startup company. It has been a ride of a lifetime for people like me who did not have a corporate background to start off with in life.

I put out my first-ever post on LinkedIn last night, asking for some advice and thoughts on how others like me would cope to survive the mentally draining, yet exciting world of startups. I was really curious. Here are some tips I’ve gathered.

Wing it till you make it

This one’s from me. Many times during the course of work, the team faced great obstacles that will make the weak-minded give up immediately and walk away. It was a fact that none of us in the marketing team were truly from the industry, nor with a marketing background and mindset.

The Imposter Syndrome

I always felt like an imposter giving briefs and proposals which I planned with research from my best colleague, the Google Search Engine. Luckily, I came from a military background. Many of us would think that a soldier is utterly useless in a corporate setting. That is quite untrue.

As a soldier, you are first and foremost, trained to follow instructions. Think about this…. Have you ever wondered why soldiers are expected to perform ceremonial foot drills that have nothing to do with warfighting? The main purpose of foot drills is to train soldiers in their listening skills and react upon a given command.

On the other end of the spectrum, you have the commanders. As a commander in the military, you are trained to give clear instructions through mission briefs and even more so, the proper execution of plans. And the last thing you want is an unclear mind because your soldier’s life will depend on your next command.

I was a Specialist from the WOSE (Warrant Officer, Specialist, and Enlistee) core, commonly known as a non-commissioned officer in the Army. Conducting operations for small groups of seven men to around a hundred soldiers was my specialty. So, this skill set did play a part in helping me survive a whole different setting for my civilian jobs after my switch from the military career.

Learn to craft good instructions and give clear briefings. Anyone can do this. The trick here is to write down everything that’s on your mind. Through writing, you can structure your thoughts to give you clarity. With clarity and a clear structure when you speak, you will look ten times more confident. The energy you give off at the start will affect how everything will end.

As a startup, you can expect a newly formed team to have a higher chance to fail at any campaigns they try to pull off. There is little synergy between team members but the best part of everything is that no one knows better, and everyone is as clueless as the next person. So everyone should try to act their part and wing it, like a great imposter who puts up a strong front in order to make things happen.

Fail once, learn from it. Fail twice, try next time

You would fail most times. My mantra is — Fail once, learn from it. Fail twice, try next time. It doesn’t necessarily mean it wasn’t a good idea to start with, but it could just be a wrong-place-wrong-time kind of situation that you cannot control. Let things go for now, and revisit when things change.

Failing at something is important for startup employees and founders. The fear of failure, or the perfecting of plans causes delays in execution that are more deadly than running out of money. As a startup with limited funding, Time becomes a currency that is of the highest value.

So, be that great actor for your team and execute the plan. Fail at it and you get to learn something. Try again and you will find either success or failure. Lastly, keep moving and go on to the next act fast.

Shut up and just do it

This one comes as a shocker. But I find some truth in this. In the initial phase of a new startup, it may be fine for the founders to run things like a dictator. For the staff, get ready to accept anything that comes, because no one knows better anyway.

Just do it. Once an agreement is reached on a decision, let’s all trust our founder’s instincts and planning, and roll with it. Just like how we would trust a good king to rule his subjects.

The most important part of this is that everyone must accept success or failure AS A TEAM.

No pointing of fingers should happen. No grudges, no nothing. Any mishandling in the event of a failed initiative would be the start of bad work culture. People who are new to working in a fast-paced environment such as a start-up or the military could give up at the 6 months, 1-year, or 1.5-year mark from my observations. Keep the team spirit alive, celebrate small wins, acknowledge failure, and apply new solutions to create better outcomes, together.

You need to “start” and be “up” all the time

A little pun intended here, but this is true. At the content creator platform start-up that I’m working in, it’s a fully remote working arrangement for everyone. I’m living the dream, or so I thought.

At first, it was like a dream come true. I’ve always hoped for a work-from-home job ever since the start of my adult working life. Yet I chose to start off with a military career which of course, required me to be physically there at my job. I just don’t know myself anymore…

As enticing as it sounds, a work-from-home life is no fairy tale. It requires a ton of self-discipline and time management skills to make things work.

Your daily challenge as a work-from-home employee starts from the simple task of waking up on time. You now have the freedom to wake up just minutes away from your official working hours, but there is a risk of oversleeping every morning if you choose to do that.

It won’t be nice if you were caught sleeping on the job, and it breaks your co-worker’s trust in you easily. This is a daily game of Russian roulette that is bound to shoot you in the foot someday if you persist. Discipline is key. If you a bum at heart and really wish to stay in bed, play it smart and at least respond to your work calls. Trust is given first and earned later. Break that deal and everything is off the tables. Not worth it.

So you have overcome the greed for sleep. What’s next?

You are now ready for work at your desk. On your own PC or laptop, the demons of distraction will now come for you. How do you ensure you do nothing but work for the rest of the day?

To be honest, it’s really impossible with the Internet at your fingertips. It will call out to you constantly, taking you away on journeys far away from the mundane work you are grinding on every day.

To overcome this, base your whole day on completing specific tasks. Split your hours and allocate them to each task, and plan them towards completion. The truth is, it is impossible for you to sit in front of your screen and concentrate for 8 hours straight with no breaks.

Be realistic and kind to yourself by planning some coffee breaks, snack time, doing some static exercises like jumping jacks, or even spending a day out working in a café. Although some may say that all these activities are nothing but a distraction, I’m sure it beats sitting in front of the screen but with your mind somewhere else. Be focused on the number of tasks completed, not the amount of time being “latently present” — being there, but not there.

You definitely should not spend the rest of your life sitting in front of the computer, in your boxers, with an unshaven face (for guys). Life is so much more. Make good use of the time you’ve saved from the commute back and forth to the office!

What’s up with being “up” all the time?

Now, let’s talk about being “up” all the time. In this dungeon of a business speed run, were you hoping for work-life balance? Probably not the best to have expectations. If you value balance, the truth is start-ups might not be the best kind of place to work at.

Messages that come in at night or on weekends are mostly bad news. Should you answer them and help settle things at work? Well, it all depends on how much you care. As an employee, I care about my work enough to say that I don’t mind working extra time. I always felt that this is the exchange for the “freedom” that I now enjoy. So in life, do practice giving and taking. You will feel better internally with this mindset. If everyone pursues their own right, nothing moves right.

But to all start-up founders out there, please do not expect this from all your staff members. You should be working the hardest as the founder. At the end of the day, this is just a job for most of them. To you, it is probably your whole reason for existence at this point in time, with all the investments and expectations poured into this start-up.

If you get a good employee, be thankful. In between all your anxiousness and anxiety attacks, just be mindful of how much you communicate with your staff members during weekends and off hours. They are keeping count, and if they are not rewarded well enough for their dedication, you will find yourself alone on this start-up journey very soon.

Tired? You are on the right track

You are supposed to be tired! Start-ups are hard work. In between all the day-to-day firefighting to solve business problems, you get brain drained without even knowing it.

You pander for support to get the buy-in of your ideas from your colleagues. You banter and debate hard to get your ideas accepted by the management. You dread looking at the sheer amount of tasks piling up and you crawl your way towards the seemingly impossible-to-fulfill KPIs set out by the management daily. On the mental front, you are fighting the good fight against procrastination. It is indeed tiring.

Deep down inside, you are hoping you had a savior or a know-it-all mentor who would come out and save you every time. How great would that be? A great leader to bring us to victory while you sit back and ride the waves. The reality is that most start-ups are made up of members of different expertise. A great marketer probably would not know how to build a great product, and a great developer would now know how to market one. A great leader is even harder to find.

Communications Matter

The constant struggle to understand each other is a daily chore you’ll have to endure, and teams might just give up totally on each other, eventually working like three different companies (marketing, product, development). It is a dangerous situation and must be prevented from happening. Once things break this way, the company is probably on the road to failure.

So, is everything worth it? Just take a step back and see how much you’ve grown. The adventure of going into each task “blind” with just a plan is exciting but frustrating. You would have understood now that you learn things the fastest by making mistakes. You learned how to put yourself in the shoes of others, and to talk in their language to get something done.

Hopefully, you learned to be kind to your co-workers and people in general, use language in good taste, and always settle disagreements in a diplomatic and logical manner.

Conclusion

The journey so far has been fun enough for me. I am not sure where this company will go in the future, but I would stay and finish watching this show. Whether we end up with success or failure, I am the beneficiary of this experience with all the lessons learned.

Who knows, I might become a founder of my own start-up someday, and go through this fulfilling hell once more. This time, it would be on my own terms.

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