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Premortem Of My Career Direction: Lessons From Poker And ‘Thinking In Bets’

Anticipating Career Pitfalls In Consulting, Writing, And Product Management


I re-read "Thinking in Bets" by Annie Duke this week and learned about terms like tilt, backcasting, resulting, and premortem.

I used the premortem concept in my career planning. Why? Studies show people who imagine negative outcomes and their reasons do better than those who only think of positive outcomes.

What if, years later, I find I've failed in my career? What might the reasons be? So, I time travel to the future in this post. Here's my introspective analysis, a candid look into the mirror of possibility.

I spent 1 hour and 3 minutes writing this post.


Ready to time travel to put myself in my future self’s shoes.
Ready to time travel to put myself in my future self’s shoes.

I’m looking at 5 career directions or workstreams.

  • Consulting

  • Coaching

  • Job Hunt Product

  • Writing

  • Full-time job search

What’s Premortem?

Simplifying HBR’s take on a premortem: In a premortem, everyone pretends that the project they're working on has already failed. This is a common reality for many projects. They then think about and discuss why it might have failed. This way, people who have concerns or doubts can share them early. This helps to make the project better from the beginning, instead of figuring out what went wrong after it's too late.

Consulting

A few years later, if I look back and my Customer Experience (PM) consulting business had failed, these might be likely reasons:

  • I offered a service nobody wanted. No one needed a product management consultant.

  • I couldn't be seen as an expert by companies because I lacked enough experience. Maybe companies wanted FAANG or 20+ years of experience. They didn't hire me as an expert, and I did not engage as an individual contributor contractor.

  • I didn't reach out to my network for consulting projects. I didn't look for companies or projects online, so I didn't get any projects.

I wrote more about my consulting attempts and shortcomings here.


Last year consulting was the main focus but with 3 types of projects around it.
Last year consulting was the main focus but with 3 types of projects around it.

Coaching

Apart from consulting, I did a few more workstreams in 2022-2023. I wrote about these workstreams here.

A few years later, if I look back and my PM job hunt coaching business had failed, these might be likely reasons:

  • I didn't create a cohort-based course, like Maven. So, I had low engagement and retention in my clients.

  • Since I had a 1-1 coaching model, my time commitment exceeded what I could reasonably charge clients.

  • I attracted interest from India or other developing countries. But, they couldn't afford my European rates.

  • Clients came to me lacking self-drive, which was why they felt the need for a coach. Unfortunately, this same lack of initiative meant they didn't succeed, even with my help. This made it difficult to get good testimonials as well. Although this could be one reason, I see this as a less likely reason because many clients who reached out to me were working hard on their own and wanted to go the next level by hiring a coach.

Resume Checker Product

A few years later, if I look back and my PM resume checker business for job hunters had failed, these might be likely reasons:

  • I spent a lot of money on automation, but it didn't increase the number of customers or TAM (Total Addressable Market).

  • One night, the product went viral. But I was on JotForm's free trial with a limit of eight paid submissions a month, so the sales got blocked and my reputation nose-dived.

  • People didn't see its value over ChatGPT, Grammarly, or free resume checkers.

  • The TAM for product managers seeking new jobs was small. Even with a good organic search ranking, I got a minuscule number of website viewers.

  • I built the product based on my understanding of the hiring process, including use of ATS (Applicant Tracking Systems). My misunderstanding of ATS meant customers did not benefit from using my product. For example, ATS might not scan resumes bullet by bullet but look for overall keywords. For example, humans may not be reading your resume ever.

  • My misunderstanding of ATS and the hiring process made a B2B pivot fail. If I pivot to B2B, my target customers will be recruiters at tech companies. But, they might operate differently from my assumptions. For example, Recruiters might overestimate the quality of their written job description. They might want to match a candidate’s resume with their job description rather than the candidate’s skills for the broad function.

Writing

A few years later, if I look back and my writing project on Substack/my blog had failed, these might be likely reasons:

  • I shared a variety of opinions instead of offering helpful tips in a focus area.

  • I struggled to enhance the quality of my LinkedIn posts, which meant they weren't effective in attracting readers to my articles.

  • People were more interested in insights from individuals with different experiences, rather than hearing from someone with my background. Readers preferred people with 20-30 years of experience or those who had worked at FAANG companies.

  • I was not consistent in my writing when my business or job workload increased.

Full-Time Job Search

A few years later, if I look back and my full-time job search had failed in 2024, these might be likely reasons:

  • The market was down, with few product manager roles in Ireland. The competition was high.

  • Most roles were in platform or cost center positions. I preferred revenue-generating or customer-facing roles, and interviewers noticed this.

  • I wasn't good at interviews, and overconfidence stopped me from improving.

  • Since there weren't many product manager roles, I applied to a variety of functions. This diluted my focus and reduced my success rate. Even when I got a job, I felt dissatisfied because it wasn't the ideal role I envisioned.

I haven’t thought of reasons I will fail in a full-time Product Management job. I’ve focused my thoughts on job search here. I’m not worried about performance in a PM role nor sure I’ll target full-time roles.

How Would A Premortem Help?

Now that I’ve thought through the failure reasons, this helps me think of robust goals for 2024. Here are some of my goals that map to each workstream. 

  • Consulting: I have sales prospecting goals. “Contact 50 people about my consulting services before 1 May 2024. I consider calling, messaging, or meeting someone as ‘contacting’.”

  • Coaching: My writing efforts should indirectly help marketing for coaching. “Write 52 blogs, similar to 2023”

  • Resume checker product: I have a focus on marketing. “Execute the marketing plan, focusing on content creation to attract paying users. Be open to pivoting the product direction.”

  • Writing: I have a goal to understand my readers. “Write posts for my reader, not myself. Start with engaging with at least 10 Substack readers and 10 LinkedIn readers for feedback.”

  • Full-time job search: I have network outreach goals. “Engage with 100 companies for full-time or consulting roles. Engagement includes applying for jobs, informational chats, consulting opportunities, and interviews.”

Reflection

I was surprised at how easy a premortem felt. It also helped me think of the viability of different workstreams. I would like to use this for more projects or activities going forward.


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