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Degree Free

How to Make Difficult Decisions and Why I Decided to Give Up Firefighting (DF#102)

Wed Jun 21 2023
decision-makingfinancial independencecareer choicesentrepreneurshipscaling a business


The episode discusses the challenges of making difficult decisions, achieving financial independence, balancing passion and practicality in career choices, scaling a business, and developing a framework for decision-making. It emphasizes the importance of clarifying goals, analyzing assumptions and outcomes, and evaluating decisions. The hosts share personal experiences with firefighting and entrepreneurship, providing insights into their decision-making processes. Listeners are encouraged to take action by using decision-making frameworks and exploring opportunities for personal and financial growth.


Passion vs. Practicality

Passion alone cannot guarantee fulfillment in a job or career path. It is important to consider practical factors such as financial stability and work environment.

Financial Independence

Achieving financial independence requires both saving and increasing income. High-earning employment or starting a business are two paths to increase income.

Decision-Making Framework

A framework for making difficult decisions includes clarifying goals, analyzing assumptions and outcomes, and evaluating decisions based on personal fulfillment and long-term goals.

Scaling a Business

When deciding whether to scale a business, it is important to consider financial goals, minimize expenses, and explore opportunities for growth.

Analyzing Decisions and Next Steps

Writing down assumptions, evaluating outcomes, and outlining next steps are crucial in the decision-making process. Limiting next steps to three helps avoid overwhelm and procrastination.

Executing and Evaluating Decisions

After executing next steps, conducting a post-mortem analysis helps evaluate outcomes and decision-making processes. Iterating on the decision-making process allows for adjustments and improvements.

Regret and Fulfillment

Regret is a complex question that depends on individual circumstances. Finding fulfillment in work can be achieved through different paths, such as helping others or pursuing personal goals.

Call to Action

Listeners are encouraged to use decision-making frameworks, take the seven-day get hired challenge, and explore opportunities for personal and financial growth.


  1. Making Difficult Decisions
  2. Achieving Financial Independence
  3. Firefighting and Entrepreneurship
  4. Scaling Degree Free
  5. Making Difficult Decisions Framework
  6. Decision-Making Process
  7. Analyzing Decisions and Next Steps
  8. Executing and Evaluating Decisions
  9. Conclusion and Call to Action

Making Difficult Decisions

00:00 - 06:55

  • People often confuse passion and work.
  • Having a framework or process for making difficult decisions can be helpful.
  • Examples of difficult decisions include choosing a certification, moving for a job, or attending a bootcamp.
  • Making trade-offs is necessary when trying to achieve goals.
  • Difficult decisions can be draining mentally and physically.
  • The hosts share an example of choosing between two job offers with different commute options.
  • The most difficult decision the host made was to stop being a firefighter.
  • The host had the goal of retiring by age 40 and learned about financial independence and early retirement later on.

Achieving Financial Independence

06:32 - 13:52

  • Financial independence communities like Cora and Reddit can provide valuable insights and support.
  • Saving is a crucial skill for achieving financial independence, but increasing income is also important.
  • Two paths to increase income are becoming a high-earning employee or starting a business.
  • High-earning employees can work at companies that offer substantial salaries or equity compensation.
  • Joining startups with market validation and potential for growth can lead to significant financial gains.
  • Building a business while still employed can help mitigate risk and provide stability.
  • It's advisable not to start a business when facing financial pressure; instead, secure a job that supports your entrepreneurial goals.
  • Being practical in career choices and money management can lead to successful outcomes.
  • Opportunities may arise unexpectedly, so it's important to stay open-minded and consider new possibilities.

Firefighting and Entrepreneurship

13:32 - 20:29

  • The speaker saw firefighting as a great opportunity to work and still have free time.
  • The speaker wanted to go back to Hawaii, their hometown, and saw firefighting as a way to do so.
  • Firefighting offered a pension, which appealed to the speaker's desire to lower downside risk.
  • The speaker aimed to retire by 40 and saw building a successful business as the means to achieve that goal.
  • It is important not to confuse passion with one's job or career path.
  • Many people feel trapped in their careers because they believe they must follow their passion.
  • Passion alone cannot pay for necessities like groceries and rent.
  • Working in a passion field does not guarantee fulfillment if the work environment is draining or unsatisfying.
  • The speaker took a practical approach in pursuing firefighting, studying for exams and preparing for interviews.
  • Despite initially approaching firefighting practically, the speaker fell in love with the job and found it fulfilling.

Scaling Degree Free

19:59 - 26:53

  • The podcast hosts loved working on a fire truck and serving the community in Hawaii.
  • They started a business called Degree Free to help people succeed without a college degree.
  • The hosts realized that many successful people didn't have degrees and wanted to share their stories.
  • They had to decide whether to scale Degree Free or continue working on it part-time.
  • They discussed the importance of minimizing expenses and increasing income to achieve financial goals.
  • Passion for a job is not necessary, but it can be helpful in entrepreneurship.
  • Some entrepreneurs take a practical approach and focus on making money rather than pursuing passion.

Making Difficult Decisions Framework

26:33 - 33:23

  • The decision was either to stay in Hawaii and continue doing what we were doing, or to move somewhere else with a lower cost of living and scale degree-free.
  • Taking advantage of fringe benefits can help you get ahead in your career.
  • The difficult decision was whether to go back to a higher cost of living area and work part-time, or stay in a lower cost of living area and continue growing the movement.
  • The decision was emotional rather than logical.
  • There is no right or wrong way to make difficult decisions.
  • The first step in the framework is getting clear on your goals.

Decision-Making Process

33:01 - 40:09

  • Getting clear on your goals is crucial for making decisions.
  • If your goal is to work from home, the decision becomes clear.
  • Writing down your goals and decision trees can help clarify your path.
  • Using a whiteboard can be helpful for visualizing and discussing decisions.
  • After clarifying goals, write down pre-decision assumptions and post-decision assumptions.
  • Narrowing down goals to one or two choices can simplify the decision-making process.

Analyzing Decisions and Next Steps

39:48 - 46:34

  • Writing down assumptions for each decision is necessary
  • The more difficult the decision, the longer it takes
  • Analyzing assumptions and outcomes helps in making the decision
  • Consider which outcome serves your goals the most or least
  • Evaluate if feeling fulfilled is more important than retiring at 40
  • Helping people made the speaker feel fulfilled as a firefighter
  • The speaker believes they can find fulfillment in their business too
  • Working in this format makes it harder to connect with people being helped
  • Outlining next steps should come after making the decision to avoid procrastination
  • Limit outlining next steps to three to avoid overwhelm and paralysis

Executing and Evaluating Decisions

46:04 - 52:52

  • Identify your next three steps, as the consequences of those steps may change the relevance of subsequent steps.
  • Example next steps: call your captain, call your chief, and call your family.
  • Keep it simple and manageable by limiting yourself to three next steps.
  • After executing your three next steps, conduct a post-mortem analysis to evaluate the outcome and decision-making process.
  • Evaluate if the outcome matched assumptions and if you used the correct system for decision-making.
  • Consider if there are ways to mitigate negative outcomes or learn from mistakes in the decision-making process.
  • Iterate on your decision-making process and make adjustments as needed.
  • Regret is a complex question that depends on individual circumstances.

Conclusion and Call to Action

52:25 - 57:31

  • Use a system, evaluate its effectiveness, and make changes accordingly.
  • The question of regret is difficult to answer; being a firefighter was an amazing experience, but it also had downsides.
  • Working as a firefighter meant waking up multiple times a night and missing out on family time.
  • Currently, there is no regret in leaving the firefighting job and helping others through different businesses.
  • The goal of the podcast is to provide frameworks for making difficult decisions and achieving goals.
  • Listeners are encouraged to take the seven-day get hired challenge or sign up for the free weekly newsletter for more content on job hunting, education, making money, and decision-making.
  • There is interest in creating content about building a business; feedback from listeners will determine when it happens.