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#2 Thoughts on Working in A Start-Up

My second post is going to be about my thoughts working in an early-stage start-up as my first job. Before I begin, I'd like to state that we are currently going through some very interesting times, with COVID-19 and riots in the US whatnot. There's also that environmental issue where Singaporeans are generating the most plastic waste per capita (a topic for another day). It seems like the economy is bleak (bleak may even be an understatement) and not to sound super pessimistic, but the economy will most likely continue falling into recession even after the COVID-19 pandemic. Things will never be the same again. Warren Buffet even testified that the air travel may never return to pre-COVID levels and then proceeded to sell his position in some major US airlines.


Start-ups are risky precisely because we are small and cash-dependent. If you've ever heard the term "cash is king", it applies especially so to start-ups. If major firms like One Championship and Grab are laying-off employees, think about what's going on in the start-up economy. The effects are blown up tenfold. Up to date, I've seen many founders downsizing or striking-off their companies. I've had friends who lost their jobs almost immediately after joining. My company itself has cut our team size down by half and we are aggressively streamlining operations and ramping up our revenue streams. It is a fight for survival. While I'm thankful that I'm still employed and that the government has been offering various grants to help us tide through these months (thank God for our budget surplus), it doesn't make the situation easier for anyone.


That being said, I believe that we will eventually learn to adapt to new normals. Amidst the onslaught of bad news we see in media, there is still a silver lining - people are picking up new skills due to the increased accessibility of online courses, the internet has allowed us to stay connected with our loved ones and being locked at home has forced us to become oddly more reflective (me included). I'd like to take this chance to share my experience working in a start-up. I know it may not be the best time to share tips since unemployment is at an all-time high, but I thought it'd be good to offer some insights anyway. After all, these storms won't last forever and I do know of some start-ups who are continually hiring fresh talents amidst the pandemonium. If you do a quick google search, you'll definitely be able to find articles outlining the pros and cons of working in a start-up but I'd like to share my own personal journey since I have and still am currently working in a start-up. Also, I'm a millennial with millennial thoughts so I hope you'll be able to identify better with me.


To provide some context, I graduated from university just last year and took the typical route of doing a Bachelors degree in Business Management. I would say I'm an average student, doing well enough just to land decent internships and pass my courses. I wouldn't say though that I'm the most outgoing person, preferring to remain low-key and participating only in mandatory social activities, but that's only because I was more focused on life outside of college. In my university, we've been conditioned to aim for the stars. MNCs and management programs were the way to go because it offered us prestige and a good starting pay among many other benefits. Not going to lie, I was sold on this idea that I would work in a high-rise building in the Central Business District (CBD), wear fancy suits and get my daily Starbucks-fix every morning (I actually still do work in the CBD and spoil myself with expensive lattes but that's not the point). It's funny how you can spend 4 years of your college life planning for a particular route and somehow life throws you a curveball and you end up on the other side of the spectrum. That's what happened to me. My dream was to work in a management consulting firm and compete head-on with many of my peers for a position in either the Big Four or The Bains and BCGs. But somehow at the last minute, an opportunity presented itself to me to work for an early-stage start-up in a rather niche industry with less than 10 employees (during that time).


I'm not going to expose my company name here (you can fish for information on my LinkedIn page if you wish) but my current company is in the digital corporate services space - meaning that we provide services like accounting and corporate secretary for founders; essentially a start-up for start-ups. It is a very unique industry and I don't think I've ever been educated much about the existence of such a company. I've been working for this company for about a year now and so far the experience has been very eye-opening. Do I regret going down this route? Well, sometimes yes, the grass is always greener on the other side. However, I believe that everything happens for a reason. Instead of harping over the "what-ifs", I've learned to embrace my situation and be thankful to God regardless of having such opportunities in life.


Now let's dive into the cons of working in a start-up (disclaimer: I can't speak for all start-ups because every company is unique but just writing from experience here):


#1 Steep Learning Curve

I think the first point applies to almost all first jobs - be it an MNC, SME, start-up, government agency, etc. What university doesn't prepare you for is the complexities of actually working, where you are somewhat responsible for making decisions on the company's behalf. It's crazy. Also, it's either because I'm a generalist or I didn't pay attention enough during my lectures, I found that there's very little of what I learned in school that could be applied to my job.


I spent the first month in my job drowning in information because I had no idea what the industry was about and there were multiple software applications I had to learn how to use (before that, I was only comfortable with social media and e-mail; typical millennial). It is a tech company after all. There was a steep technical learning curve where I had to familiarise myself with accounting concepts and build my knowledge on the various regulatory processes and deadlines. As I was in a position where I had to advise others on compliance matters, there was little room for me to mess up.


On top of that, for the longest time, I struggled in crafting a professional e-mail. I know it sounds so stupid - like who doesn't know how to write e-mails? But trust me, professional e-mail writing is one of the most overlooked yet essential skills you must have in a workplace environment. There are actually frameworks created to craft a proper e-mail from the tone to choice of words, etc (comment if you'd like some tips). I am a very direct person and have made mistakes by being too defensive/upfront when writing to clients or attaching a web link leading our clients to our competitors' webpage (a rookie mistake). FYI, my manager had to conduct 1-on-1 sessions where she taught me how to structure a proper e-mail and for weeks, she had to vet them before I was allowed to send them out to clients.


Be prepared to have your mind-blown the moment you start your first job or when you transition to a new field. It took me approximately 2-3 months before I became (mildly) comfortable in my role. Even today, there are concepts and soft skills that I still lack but life is a continuous learning journey anyway. What's important is that you humble yourself, admit it when mistakes are made, and ask for feedback so you can improve and be better at what you do.


#2 It is Messy and Unpredictable

This point is especially true for start-ups because roles and job scopes are not clearly defined. There isn't a clear career progression or chain of command. When I first started, I found myself doing lots of admin work and data entry even though it wasn't exactly part of my job scope stated in the contract. I found that precisely because we were in such a dynamic and fast-paced environment where we were less than 2 years old and had a headcount of fewer than 10 people, you have to be a jack of all trades. It was initially really uncomfortable being surrounded by so much hubbub and uncertainty. Some days I was put in a position where I had to make tough client-facing decisions on the spot, some days I had to explain the basics of accounting to someone 40 years my senior and other days I had to resolve technical difficulties.


There simply isn't a day where I was doing the same thing. In a way, it makes my life quite exciting. It's like turning up at a restaurant and not knowing what's going to be served for lunch (some of you may see this as terrifying). Of course, as time goes by and the team expands, you kind of find some rhythm and routine to what you are doing. However, you have to always be on your toes to expect the unexpected because you'll never know when an investor will suddenly buy-out your company and do a major restructure.


Four months into this job, I was thrown in the deep end again when I had to switch departments. Just as I was getting the hang of my job, my manager made a proposal for me to be part of the sales team. I, for one, am very uncomfortable with doing sales. There's just something about it that irks me. Maybe it's the fact that I had to deal with rejection a lot more or the fact I had to engage in a lot of small talk at networking events or a combination of both. I struggled a lot internally because while I loved challenges, being in a new role meant that I had to start from square one again. You should ask my friends - the day leading up to my official transfer was miserable. My spirits were down and I was so fearful of the "impending doom" that was approaching.


Eventually, with the guidance of my mentors, parents, and friends, I accepted the fact that I had to give the sales role a shot. I constantly reminded myself that there is only growth in discomfort and channeled my competitive spirit into setting goals for myself to achieve. Every time I met my own targets, I felt a real sense of accomplishment. Even though I'm not loving this new role, I've slowly learned how to be okay with sales and I can proudly say I'm doing a pretty good job at it.


#3 Lack of Long-term Security

If you read articles on Forbes, you may have come across a headliner like "Nine out of Ten Startups Fail". I'm not going to delve into the reasons why start-ups fail (you can read the articles on Forbes or HBR if you want) but I have to agree with it. I work with many start-ups and in my one year of work, almost over 50% of our clients have shut down their business. This is not only because of the COVID-19 period by the way. Knowing facts like that is enough reason for someone, let alone a fresh grad, to be skeptical about joining a start-up. After all, who wants to join a company only to have it shut down after a few months?


While I'm not going to promise you rainbows and sunshine, I think what's important is to understand your own risk appetite. Who's to say that you won't get retrenched even if you join an established company with deep pockets? There are statistically higher risks when you join an early-stage start-up, especially one that has not fundraised, but if you are someone who is willing to take the chance, joining a start-up can be very promising. This brings me to my next part...


The pros of working in a start-up:


#1 Huge Responsibilities and Accelerated Growth

I was the first member of my (then) department when I first joined. It was truly an experience because I was tasked with the responsibility of setting the direction of the team and creating SOPs to put in place. There was no point of reference and little guidance was given to me. After my teammate joined, we both had to figure out how to insert ourselves into the company's workflows (which was really messy at that time) without disrupting current operations and basically build the department from scratch. It was a time where we were constantly experimenting, testing out new concepts, and running around like headless chickens. It was like a mini consulting project we had to take on with no budget. Needless to say, the whole experience really grew me as a person.


Firstly, I learned how to handle huge responsibilities. Knowing that the future of the department was in our hands, it was essential that my teammate and I built solid foundations in place so that future members would have a proper training guide. Secondly, I learned how to handle workplace relationships and put the needs of our company above ours. Having two new members come in and make major changes to the status quo definitely did upset some colleagues but we had to compromise and negotiate and find a solution that works best for all of us. I also had to navigate and work around having vastly different work management styles from my teammate.


Thirdly, I developed time and project management skills. My teammate and I had to own this mini-project of ours by utilizing resources and delegating work to others while still working on our day-to-day tasks. Lastly, I learned how to handle failure. This was difficult because no one likes to admit that they are wrong. However, there is this Chinese saying that failure is the mother of success (I'm using a lot of cliches in this post). There were times where I made critical mistakes and that only made me become more careful and meticulous in the future.


As compared to my time when I did an internship at a big firm, I was given responsibilities I didn't think a fresh grad could handle. Of course, I can't compare apples to oranges but I don't think I would ever have the opportunity to speak with my CEO if I was working in a large corporation. Here at my start-up, I work closely together with my CEO and could constantly bounce my ideas across to him. The amazing thing is that he actually listens and does not just pass them off because of my inexperience. You get heard and credit is given where credit's due. But don't just take it from me, you may think that I just got lucky.


A close friend of mine is also working in a start-up and he gets the opportunity to take solo trips overseas in order to survey other markets. He is given the responsibility of coming up with a solid plan to expand overseas and is in charge of establishing major partnerships for his company. Now, who would have thought that someone with less than a year of experience could do all that?


#2 Thriving in Ambiguity

There is a very common term that we live in a VUCA world - volatile, uncertain, complex, and ambiguous. I admit that structure gives all of us comfort but the reality is that nothing is really certain in life. The faster you realize this, the better you will be equipped for what life throws at you. What better way to train to be comfortable with the uncomfortable by working in a start-up? I am aware that there are many ways but I'll just be focusing on this method in this post.


Precisely because of how messy and unpredictable things get, you develop this sort of second nature to dealing with ambiguity. We are creatures of habit and the more times we get exposed to something, the more used to it we become. I'm sure that every job has its own challenges and uncertainty but all I'm saying is that personally, I have become more attuned to dealing with curveballs. I love being in control and used to hate it whenever things don't go according to plan, sometimes I still feel this way, but I've grown a lot to be fluid and adaptable to my circumstances. In the end, there is only so much in life you can control and one of it is your attitude and mindset. Easier said than done but I can attest that I was a much more adaptable person now than I was in my uni days.


#3 Tight-Knitted Community

If you ask me what I liked most about working in a start-up, I have to say the tight-knitted community. This is more of an emotional reason than a rational one because I am an emotional person. It's hard to form genuine connections with everyone in your company if there are over 1,000 employees. Most of the time, you only mingle with your department or project mates. While office politics are always present, I find that it is so much easier to make friends with your colleagues in a cozy environment. The people in my company are not just work-colleagues to me. We actually chat with each other outside of work, organize game nights with each other, and occasionally attend fitness classes together.


On top of that, this sense of "tight-knittedness" also extends across the entire start-up economy. Perhaps it's because start-up founders understand the struggles of other start-up founders, there is this sense of unspoken camaraderie between companies. I love how start-ups are always collaborating with one another. Up to date, we have worked together with many start-ups/clients on co-hosting events, launching webinars, and even introducing and referring potential clients to each other. It is very heartening to know that we support one another and even though we have direct competitors, founders respect each other as human beings.


I'm not saying that joining a start-up is the way to go because I know that this path is simply not for everyone. Am I going to work in a start-up forever? Maybe, but I'd definitely like to keep my options open. We never know where the tide will lead me next. I just hope that this post gives you another perspective on what it's like to take the road less traveled and if you are looking to try something different in the future, I'll be happy to provide more tips on how to make the journey more enjoyable.

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