The Startup Lottery: Your Guide to Naigating Risk and Reward – Chapter 5

This chapter is all about how to find a job that is the right fit for you. While the author centers it around finding a role within a startup, his tips can be applied to any job search, in my opinion. The author refers to the hunt as a way to go about finding the right opportunities for you and to avoid picking jobs haphazardly. Hunters typically have a specific prey or goal in mind, they set themselves up for a successful hunt, and strike when opportunities present themselves.

The author recommends that the reader create a ‘Career Thesis’, similar to an investor’s investment thesis. An investment thesis is a stated focus that defines the kinds of companies they invest in (Bessalel, 74). 1 Investors don’t just throw their money around; they research hundreds of potential investments and then narrow their focus down to where they would like to invest their money. One can follow a similar path when on the job hunt and narrow in on areas you are passionate about and tasks good at.

The author also recommended utilizing a career decision matrix to help look at jobs from a logistical perspective while articulating key priorities in your decision-making process on the hunt. Upon further research, this sounded a lot like the Pugh method, “a weighted decision matrix, allowing you to weigh the factors that are important in your decision against each other when making your choice. Thus, it can help you think more rationally through all the factors you need to consider” (JVS Oronto).2 The ASQ article, What is a Decision Matrix?, lists this as a decision-making tool to establish a list of weighted criteria and evaluate each option against those criteria to prioritize your options (ASQ).3

I think this tool could be extremely helpful in the job hunt. Bessalel mentioned that “No job is perfect; there are pros and cons to every opportunity you come across. Systematically considering your priorities and looking at options through a decision framework that weighs your priorities helps you target prospects that are a better fit” (Bessalel, 77). Utilizing a tool like this, especially if you are coming from a perspective of panic or worry in finding a new job, is a great way to help not only acknowledge any red flags you may come across, but also help you avoid getting too excited or ahead of yourself and making a rash decision. I want to close on this last quote from this chapter, because I feel that it has some career advice I’ve personally not heard in many places, and that it could be helpful:

“It is better to seek out opportunities where you see yourself potentially settling in for the longer term, open to the possibilities that you and the company can grow and flourish together. In other words, be a hunter. To maximize your chances of finding what you’re looking for, you need to be clear on what you are hunting for and be proactive in setting yourself up for success:

  • Stay focused on your goals and build your skills.
  • Develop your career thesis so you can evaluate opportunities through an established decision framework.
  • Make your career interests and skills known through your LinkedIn profile, resume, and social media or on a GitHub profile if you are a technical professional.
  • Put yourself in a position where you become recognized as a go-to person in a particular sector or discipline or with valuable, transferable skills.
  • Keep building out your professional network on an ongoing basis (Bessalel, 83-84)”.

I am curious to hear your thoughts on this week’s reflection and what you think about the tools provided!


  1. Bessalel, Gus. The Startup Lottery: Your Guide to Navigating Risk and Reward. Jones Media Publishing, 2023, pp. 74-84. ↩︎
  2. Lewis, Karin. “Struggling to Make a Career Decision? Try This Helpful Tool.” JVS Toronto, 1 Oct. 2018, https://www.jvstoronto.org/blog/struggling-to-make-a-career-decision/. ↩︎
  3. “What is a Decision Matrix? Pugh, Problem, or Selection Grid.” ASQ, American Society for Quality, https://asq.org/quality-resources/decision-matrix. ↩︎

8 thoughts on “The Startup Lottery: Your Guide to Naigating Risk and Reward – Chapter 5

  1. Hi Meaghan,

    I really enjoyed this blog post on being intentional with our job search and focusing on building a career. I agree that we should take our search seriously and not settle for anything that completely misaligns with our long-term goals. However, I also think it is important to recognize that waiting for the “perfect fit” can sometimes be counterproductive.

    For example, my father-in-law left his job of 25 years because he was no longer “feeling it.” It was not a planned or strategic move, just a gut reaction. That was over ten years ago, and he is still unemployed because he is holding out for something that feels just right. Unfortunately, this decision has placed a significant financial strain on the family. While that is a pretty extreme case, I have seen others go through similar situations, turning down opportunities because they were not ideal, while missing out on chances to build their resume, learn new skills, and connect with people who could help guide them toward a more fitting career down the road.

    Sometimes, taking a job that doesn’t feel like the end goal can actually serve as a stepping stone. It gives us a chance to work, grow, develop references, gain experience, and build our reputation. No job should be beneath us, and the effort we put in now speaks volumes to future employers. Plus, who knows what opportunities might come through the connections we make or the skills we gain while we are “in the meantime.”

    Sorry for the rant. I have just had this conversation so many times with friends and family who are still waiting for the “right fit” instead of getting started where they are. Let’s not let pride or fear hold us back from moving forward.

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    1. Hi Samantha,

      I could have sworn I hit the reply button after you first commented, but I apologize for dropping the ball on this one!

      I think you are totally valid for your thoughts on the right fit, you do not have to apologize. There is a difference between wanting something that works for you/your goals and wanting the impossible. I know I have been in the position of not feeling a job and feeling somewhat desperate for something better, but I have never been able to be in a position to wait for the right fit.

      I like your point on using not perfect job fits as stepping stones or resume builders, I think that is a wise choice to do if you’re looking for that perfect fit – it can help get you in a better position to take on a role that is the perfect fit.

      Your take is very important to this conversation and I thank you for sharing it!

      Like

  2. Meaghan, I really appreciated your breakdown of this chapter—especially the way you linked the “hunter” metaphor to real-world tools like the career thesis and decision matrix. That connection between clarity and intentionality is so important, especially in a world where job searching can often feel reactive or rushed.

    Your explanation of the Pugh method made it feel incredibly approachable. I agree that having a structured framework is invaluable—not just for filtering opportunities, but for avoiding emotional decision-making during stressful times. I’ve definitely seen people (myself included) get swept up in panic-applying, only to land in roles that didn’t align with their long-term goals.

    I also loved the quote you ended with. That idea of “entry with intention” really stuck with me. It’s not about waiting for the perfect job, but about understanding our priorities and recognizing when something has the potential to grow with us. That shift—from just finding a job to building a long-term fit—feels like a major mindset upgrade.

    Thanks for another great reflection. You’ve got a talent for making these concepts feel both practical and personal.

    Warm regards,

    Brent Parker

    Owner – Resilience Repurposed LLC

    Graduate Student – WCU (M.E.I.L.E. Program)

    https://blog.resiliencerepurposed.com

    Like

    1. Thank you for your comment Brent, I feel silly talking about myself and my experiences so much in these reflections sometimes so I am glad to hear that it’s been appreciated from at least one person.

      I am someone who needs a bit of structure as I learn new methods and things in general, so the Pugh method appealed to me as well. I feel that it is something that can be adapted as I get comfortable with it – even though I hope to not have another job hunt anytime soon.

      I loved that quote as well, I didn’t expect it to hit me as hard as it did, but it really struck a chord with me. I don’t think I could have defined it any better than you did, but you hit the nail on the head!

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  3. Hi Meaghan,

    This chapter really made me pause and reflect on my own journey. I’ve been with the same organization for over seven years, and unlike the traditional job hunt described here, I didn’t go through the process of actively seeking a role. I was fortunate to be chosen as a student, and from there, so many people around me poured into my development—mentoring me, challenging me, and helping me grow into the role I have today. I genuinely love what I do and the impact I get to have every day, and I’m incredibly grateful for the way my path unfolded.

    That said, this chapter gave me a deeper appreciation for what the traditional job-seeking experience looks like—especially for students or early-career professionals who are navigating it without the same kind of support I received. The concept of a Career Thesis stood out to me as both powerful and practical. I can see how clarifying your purpose, values, and strengths before starting the hunt would bring much-needed direction to a process that can otherwise feel overwhelming and uncertain.

    The decision matrix tool is also something I’ll be sharing with students I encounter. It brings a layer of intentionality that’s so easy to overlook when you’re feeling pressure to land something. I loved the quote about seeking a place where you and the company can grow together—it mirrors my own experience and reminds me how important long-term alignment can be.

    Overall, this chapter was a helpful lens for me to better understand and support others who may be earlier in their journeys. It also reminded me not to take for granted the value of mentorship, investment, and being seen. For those actively hunting, I think this framework is a strong guide for both clarity and confidence.

    Best,

    Freddy

    Liked by 1 person

    1. I am so glad to have provided a resource for your students! I agree that it could be really helpful on their journey post graduation.

      As someone who was kind of lost or stuck after graduation, I wish I had someone who could have shown me a tool like the Career Thesis. I feel like it would have saved me a lot of heartache from not finding the “perfect” job and would have helped reduce the sense of desperation that came along with the search.

      I am so happy that your path has been so beneficial to you, it goes to show that hard work does pay off in my opinion. Had you not made an impact as a student worker, there is no telling where you would be in your career journey at this point.

      Thank you for your kind comment Freddy!

      Like

  4. Hi Meaghan,

    I really enjoyed your reflection on Chapter 5, especially how you connected Bessalel’s Career Thesis concept to an investor’s mindset. That analogy makes so much sense! It is easy to approach a job search reactively (especially when there is pressure to land any role), but framing it as a strategic hunt with intentionality is such a game-changer.

    Also, your point about the decision matrix (and the Pugh method) was one of my key takeaways. In the past, I have definitely fallen into the trap of getting excited about a job’s perks while overlooking misalignments with my long-term goals. Needless to say, it was not a fulfilling role for me. Having a weighted framework to assess opportunities objectively is a great way to balance optimism with practicality.

    GaVonne

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    1. I am so happy to hear that this was a great takeaway for you!

      I have also found myself distracted with the shiny parts of a job and ended up in a misaligned role as well. I really appreciate the objective nature of the decision matrix, we all have unconscious biases and if I am distracted by the perks or a role, I could see myself unintentionally skewing my grading.

      I feel like the fear of layoffs and budget cuts in recent years have made everyone have a slight fear based view of job searching, and overall just makes it harder. When you are able to objectively look at opportunities, I feel like it helps remove the fear aspect of the hunt and help you feel more confident and in control in a way.

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