A kind soul on Mirror’s Discord channel responded to my exhausted rant through a direct message about how no one is a failure as long as they are alive. That was beautiful but I’m still disillusioned with myself, hence this post. I promise to write about other things going forward, but today I’m going to treat this post as therapy as I don’t have enough money to afford a therapist I think I badly need.

I never had a conventional and steady career. Took whatever opportunity that came in that could pay me some money and eventually ended up disliking the role or discontented with the pay and so on. In my recent longest stint at a big organisation, I left on bad terms. I also didn’t have a great relationship with one of my bosses here and that impacted me negatively, mentally, financially (didn’t really get too many salary raises, which frustrated me) and overall, professionally. The previous boss was great because he was intelligent and fair but also a terrible communicator. I worked very closely with lots of teams and people managing global projects and eventually realized I’m fed up of this shit. I was tired of building consent, aligning stakeholders, and keeping the ship afloat each day. As a project manager you realize soon enough that the success of projects is always attributed to the team and failure always rests on the captain’s shoulders. Through this period, I also realized I used to be crippled with fear before meetings where I had to organise my thoughts and lead discussions. I would invariably end up offending people and I used to blame it on my inability to read between the lines, gauge people’s motivations, soften the rough edges of snappy conversations. Sometimes, I blamed it on the natural tone of my voice and I just didn’t know how to modulate that to sound more friendly and assertive but not patronising.

I knew I wanted to do something with numbers like financial analysis, research or manage money in some way but I wasn’t sure what exactly that was. I enrolled in the CFA program and started to engage with the community that helped me understand the various options and career trajectory within this industry.

I dabbled with Private Equity and finally settled into Venture Capital in the last couple years while also angel investing on the side. I loved meeting all the freshly minted founders, their enthusiasm towards the work they did and told myself ‘I would love to build something myself but I’m too old for this now’. I convinced myself that I will be part of a future revolution by investing in good founders I believe in and that’s my contribution towards humanity’s progression. I thought technological innovation and efficient capital allocation was my calling. While raising capital for the first VC fund, I realized how hard LP money was to come by. While I see this crazy influx of money into VC all around me with people talking about how they raised millions in their first fund, we were struggling to raise a fraction of that amount. We spoke/reached out to friends, angels, fund of funds, not-for-profits etc but only saw closed doors. Eventually, we deployed whatever was pooled by the business partners into some companies and wrapped it up. My business partners had other interests they decided to pursue and I thought I did as well.

I began my quest to singlehandedly launch a fund that will invest in the highly underserved communities of emerging markets where there are many barriers to entry, poor infrastructure but some very engaged and enthusiastic potential-entrepreneurs. I designed a model to provide seed capital and set up a framework to offer support via another local group for marketing, tax, legal etc so that founders can focus on product. It took a lot of chasing via calls, emails for people to respond to information requests or meetings with founders with some of the people I was working with. I didn’t find the model to be viable anymore when relationships are getting built through scratch during COVID times and there was no sign of being able to meet or see the people I was going to work with. I was also met with skepticism when I spoke to other funds and not-for-profits about funding options for this unique fund. Given my very brief stint in VC, I shouldn’t be and wasn’t surprised at this reaction. I was told by many people that it’s a great idea but execution is key.

While the discussions for this fund were ongoing, I continued to apply to a program that was accepting applications for an accelerator to start your own VC fund leaning towards social impact. I thought it would be helpful to get some structured guidance to improve my VC operational skills and help me think through a good fundraising strategy. I applied twice and got rejected both the times (I was a finalist the second time).

Soon after, I was speaking to another VC fund that would be investing in women entrepreneurs only. The initial discussions were positive and I was told in the third meeting they need someone that has considerable fund raising experience, so I was then out of the race.

In between all of this, I find out that I have failed the Level 2 of CFA program for the second time. I had studied for this exam a total of 4 times - the 2nd and 3rd attempts were cancelled one month prior to the exam due to COVID. Any CFA program participant will tell you that preparations go on for months in advance for these exams. I used to find it very hard to grasp and retain all the concepts, so I had started to prepare 3-5 months in advance for the 2nd, 3rd and 4th attempts and around 6 months in advance for the 1st attempt. The day the results were out, I decided never to attempt the CFA again as it literally put my life on hold so many times that I can’t afford the money, time and energy anymore. Also, since I wanted to continue with private investing as my career path, I didn’t see the need for these credentials anymore. I joked with my friend that it feels liberating to decide not to pursue this designation anymore in a way that you leave behind your toxic spouse forever.

In between all above, I tried reaching out to many individuals (friends, spouse, LinkedIn network, a few strangers and even a very expensive career counsellor) to help me identify what career option is well suited for me. A lot of people were encouraging and generous with their time and advice. I acted on some of the advice I thought might help me and landed a few interviews here and there. Here is where a beast would show up. I would be crippled with self doubt and anxiety thinking if this person will actually see me for the failure I’ve been in the past, for the difficult professional and personal relationships I have had, for the conflicts I created and those that I fled. I can hardly even remember coming out of interviews thinking ‘wow, that was good conversation’. I was never relaxed before or during the interviews. After every single one of them, I felt a huge sigh of relief that it was over. I didn’t get selected for any of these jobs except one which was a few corporate levels below my experience. I didn’t hear back from them until a week prior to joining date where they said they have decided to scrap the role altogether.

Exhausted and tired of rejection, I decided to take a break but the financial commitments and the feeling of not wanting to quit keeps me going. I was always curious about Blockchain and Crypto with all the buzz since pandemic hit. I decided to read up on this topic and see if there is something here that I might find as my calling. I like how powerful the technology is, its underlying values of privacy, transparency and all the good stuff I’m not going to re-iterate because we all know it. I’m particularly curious and hopeful (based on my limited understanding of this technology at this point) that one day it will effectively change education and healthcare outcomes for the very poor sections of our societies. So anyway, back to my oscillation between rejection and hope - I feel fearful and happy about my life at different times and I’m trying to find out which of these parts of me can be more constant and who is the impersonator. I’ve now thought of trying my hand at learning more about the Blockchain technology, some of the projects and find what might interest or move me. I found a few interesting companies and people and reached out to them to help manage their communities. I do one for free now but continue to look for some gig that can pay my bills. I’m also applying to other roles that are non tech but like I mentioned earlier, I have bombed two interviews so far that should have been easy scores. So, I’m just wondering what is so wrong with me that I cant exude confidence, enthusiasm or whatever it is that people look for in these interviews.

I’m going back again and again to this idea that I wish I can do something of my own where I don’t have to worry about someone choosing to select or reject me for a role. I can feel failure in my breath each time I send an application out and keep refreshing my email account all day to see if anyone has responded with an interview call. I’m going to keep applying and interviewing while I continue to take some more courses in Blockchain, Crypto, DeFi etc. I’m also considering teaching myself some blockchain coding. My hope is for people to see me for my work that can be judged more objectively (such as code) rather than subjectively.

Thanks for reading - if you have made it this far. I needed to put this out as part of processing a few things. It felt good. I will hopefully write more productive content once I decide what I’m going to do with my life professionally. This may continue to change over time, I don’t know yet.