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Why I chose a corporate career after a failed startup

In this essay, I reflect why I chose a corporate career after a failed startup journey.

Recently some entrepreneurs came to me with the following dilemma: their startups are not going anywhere and they are considering shutdown. Some of them started as entrepreneurs for all their lives, have families in the process and have never considered the possibility of going corporate. Hence they thought about making a career switch. The follow up question from them was, “Why did you choose a corporate career and was it tough for you to manage the transition?” After explaining my rationale to them on various occasions, I thought that it might be good to share my perspectives on why I have decided to do that before starting up another company within the next 5-10 years unless something cropped up.

To answer the question, the first thing you should do is ask yourself the question, “Where do you see yourself in 5 years time?” It is the same question which I asked potential employees or interns during their interviews. My belief is that good managers genuinely ask this question with the intention to know whether he or she is aligned with the person and at the same time, work out whether he or she can help to groom the candidate to the next stage of their career. I do the same for people I hire and I look for managers who do the same or help me grow in the future. I typically do not take up a job if I can sense the slightest detail that something is not right about the person.

To guide you the process, here’s my answer to that question and I explained this to people who asked me the question. Within the next 5-10 years, I am going to do another start-up but this time, I will be the CEO of the company, providing the strategy and vision and at the same time, leading and managing a team that can scale from one to 10K employees if it worked out. Before I do that, I reflected on what my weaknesses are in the last startup and pondered about the strategic mistakes we made collectively as a company that led to her demise.

By being self-aware and really honest about my vulnerabilities, I have came to the conclusion that I have to acquire the following set of skills: ability to strategise and take long term view, managing multiple teams and work with larger cross functional teams across different regions and learn how to scale a company by understanding and implementing processes & systems. The best place to learn these skills are not in a startup or a mid-level enterprise, but in a multi-national corporation. Yes, there is the bureaucracy with processes and systems that would hamper you given your own entrepreneurial roots. The way to handle that is not to dismiss but to have a clear understanding on why they are implemented in the first place and how you can work around them without creating chaos.

When the job in Vistaprint came up, it was a start-up role, because I am tasked to lead a team which takes ideas to prototypes from senior management of the company. At that moment, my bosses were not hired and I grabbed the opportunity to learn strategy, business development and financial projections. I did not stop there. They have some internal learning systems for management and I just took the spare time from a hectic schedule to read the articles during lunch and started to weed out the missing gaps I have. At the same time, I learned how to cooperate with different cultures from emerging economies such as India and Indonesia, and more mature economies such as Australia and Japan. Those experiences helped me to grow as a person and guide me towards where I want to be in general management. I did not let my specialised role sandbag me into career opportunities limiting to going towards technical roles but I learned everything I need to be a good and effective executive or general manager in the future.

What is rewarding is that I am learning about what makes a company successful because at one point of their lifetime, they were startups. Once I understand where my objective is going to be, I can build a roadmap for myself to get back to where I want to be in 5-10 years time.

Of course, there are other practicalities as well. To be upfront, during that period of time, I was without salary for a few months, got married and after two months, expecting a baby and got myself to a mortgage. One of the fortunate principles I managed to hold close to was not to be desperate. I really spent my time working on finding the correct role for myself and not let finance be part of the equation. It is hard but it’s worth it because you are going to spend some years of your life to be there. Once you get this right, the transition into a corporate career becomes simpler and easier in the process.

Getting a corporate job has helped in many ways to help and finance another one of my startup called family, and we have managed to stabilize the household with owning a home and our daughter getting medical cover from the company insurance for an unexpected condition that came up. Over the past one and half year, I am paid properly while learning the skills I can cultivate for that future I want to build not just for myself now, but for my family. Overall I have worked with a lot of smart and kind people in Vistaprint at the same time, and I am proud of the things that we have built for the company as a team. While working hard on my corporate role, I gave some time to help the team in SGE which subsequently led to its acquisition from Tech in Asia, stayed connected to the ecosystem as a connector and now an angel investor looking for interesting companies to invest.

As I am committed to my goals, one of the hardest thing I have to is to turn all other opportunities along the way – turning down all offers to be CTOs or senior engineering roles for other startup companies. It is not them but their goals do not align with mine at that point in time. If it is not clear by now, this is also my answer to people who have been constantly asking or begging me to be their CTOs and it’s a no, and this is why. So, it is the same advice that I give to people when they decided that they want to go into the corporate route for a while.

By the way, I have not found that startup idea yet but I am constantly exploring and analyzing new ideas and opportunities. While that is happening, I can spend my time cultivating the set of skills that I truly need for the future: to be an effective executive.