written by Fabiano
7 min read

How to Make Big Decisions: Toolkit for Entrepreneurs

Structure

Quick intro 

What’s the problem?

Growth, in entrepreneurship and in life, happens through risk and stepping outside your comfort zone. And often, it’s easier to think about the next (uncomfortable) step than actually taking it. Because with every step into a new direction, you have to leave the old path behind. In this article, I'll share a toolkit to help you make big decisions that imply leaving your comfort zone - to make growth happen for you within your entrepreneurial journey.


Own background

What’s my context/experience with big decisions?

When I look back in life and especially my (still very young) professional career, change was always a big enabler for new learnings and opportunities. And each time I had to leave something behind, it felt sad first, but paid off afterward: 

  • After my bachelor’s degree I left Cologne and all my friends there behind to move to Berlin for my master’s. I could’ve done the same master’s in Cologne within a city and environment I deeply enjoyed, but I decided to pursue the unknown.
    → Met musicians who inspired me to start Livria (my first startup).
    → Got to know the startup ecosystem. 
  • After my master’s in Berlin, I joined a fast-growing, small company as a developer. I was the only developer in the office and had the opportunity to take on responsibility from day one. After four months in, I got an offer from Google to join a graduate program in Dublin. I loved my life in Berlin, working 30 hours per week as a developer and having the rest of my working hours to build my own startup (a platform for underground musicians). Plus, I had never thought of moving to a city like Dublin before and had no experience with Cloud technologies (the area I would be transferred into after the program in Dublin ends). However, I decided to go to Dublin.
    → Learned a lot about business, sales & cloud technology.
    → Saved some money to bootstrap my next startup.

Two and a half years later, after one year in Dublin and being back in Berlin and having worked one and a half years there as a full-time employee at Google Cloud, I reflected on my professional life. It was during the New Year's Eve break, just entering 2025, when I decided that I want to take more risk to pursue my goals as an entrepreneur. I decided to leave the amazing team, free lunches at the offices around the world, exciting business trips, and the salary I never would have dreamed of behind to go all-in on building my own company. Probably the most difficult of my ‘out-of-comfort-decisions’ so far.
My first day of self-employment is today. And since I made the decision three months ago, there has not been one moment of regret, but only gratitude. Gratitude towards the time I had so far and to myself for taking the steps that (I believe) will lead to great entrepreneurial experiences and growth.


Toolkit for Big Decisions

How do I tackle big decisions?

Let’s zoom in on the process when you’re facing a life-changing decision. For me, the time until taking the final decision varied depending on the weight of the decision and the potential impact of it. But I feel like the following toolkit can be helpful no matter the timeline in which you make the decision. 
This toolkit focuses on key factors that can play a role in making an impactful decision for your professional life: money, fear, status, lifestyle, vision & purpose, values, and relationships. You want to be aware of the aspects that influence your decision, and you want to reflect on them. Doing so will make it easier for you to make and stick to your decision, even if it means taking on new risks or entering a more uncomfortable phase in your life. 

Image about Key Factors for Big Decisions
Key Factors for Big Decisions

Go through and reflect on each factor that is relevant to the specific (potentially life-changing) decision you’re taking next.

Factor 1: Money

Questions to ask:

  • What is the potential short-term impact of my decision on money?
  • What is the potential long-term impact of my decision on money?

My example of deciding to quit my job at Google:
Short-term impact? Way less monthly income.
Long-term impact? Potential for growing a company that significantly exceeds my Google salary. 


Factor 2: Status

Questions to ask:

  • How would my status be impacted?
  • How important is my status? How much ego drives my answer?

My example of deciding to quit my job at Google:
How would my status be impacted? From Google employee to (not yet successful) Entrepreneur.
How important is my status? How much ego drives my answer? Not important at all as far as I do what aligns with my mission and values. My ego might be hurt about the ‘status downgrade’, but I’ll get over it.


Factor 3: Lifestyle

Questions to ask:

  • How would my lifestyle change?
  • Do I have to make compromises? Are they permanent or for a specific time?

My example of deciding to quit my job at Google:
How would my lifestyle change? Less spending in day-to-day life (restaurants, travel, etc.). More freedom with my time. More quality time with friends & family because I do not need to side-hustle after my day job anymore. 
Do I have to make compromises? Are they permanent or for a specific time? Compromises in terms of money for gifts & travel. I believe in the fact that it’s just short-term.


Factor 4: Vision & Purpose

Questions to ask:

  • How well does each side of the decision align with my long-term vision?
  • How does each side impact my future entrepreneurial career?

Exercise to do:
Sit down in a calm place. Close your eyes and visualize a room with five chairs. On each chair sits one version of you:

  • You at 6 years old
  • You at 18
  • You at 30
  • You at 50
  • You at 80

Approach each of them and ask them about advice. Take your time to imagine what they would answer. The answers can give you a great overview of how important your decision is for your purpose and vision in life.

My example of deciding to quit my job at Google:
How well does each side align with my long-term vision? Deciding to go full-time entrepreneurship aligns with my long-term vision of building up a business that helps entrepreneurs grow their purpose-driven businesses without hustling 24/7. 
How does each side impact your future entrepreneurial career? Quitting Google will give me the opportunity to fully focus on my entrepreneurial career and learn & grow as a founder.


Factor 5: Values

 Question to ask:

  • How well does each side of the decision align with my values?

Exercise to do: 
Imagine your funeral. Everyone you admired, loved, and worked with is attending. Pick 3 persons you know: 1 family member or good friend, 1 business partner or co-worker and 1 person you deeply admire. What do you want them to say about you in their speeches? Write it down & identify the values within their speeches. That’s what you want to stand for. Ask again: How well does each side of my decision align to my values?

My example of deciding to quit my job at Google:
How well does each side align to my values? Some of the values most important to me are freedom, creativity, and self-actualization. Taking the jump to bet on my own entrepreneurial journey feels like a great alignment with my values.


Factor 6: Relationships

Questions to ask:

  • How would my decision impact my relationships?
  • If there are compromises, are they worth it? Are they only short-term?

Exercise to do: 
Pitch both sides of the decision to close friends, family members or your partner. Ask for their honest advice. Also talk openly about the factors that might impact your relationship to them. Reflect about how you both envision your relationship in the future (for each side of your decision).

My example of deciding to quit my job at Google:
How would my decision impact my relationships? Instead of working two jobs for up to 60 hours a week, I switched to a 40 hour week in which I have enough time to develop my relationships and spend quality time with the people I love.


Factor 7: Fear

Question to ask:

  • What is the worst case scenario that can happen after taking the decision?

Exercise to do:
Think about the time after making the decision. Imagine everything goes wrong and not as expected. Write it down. Actually having thought of and seeing the worst case scenario written down helps a lot to overcome the fear of risk. Otherwise, your fear is undefined and just sits there, in the back of your head. Writing the worst case down might also lead to the insight that it’s actually not as bad as expected.

My example of deciding to quit my job at Google:
Worst Case Scenario? I completely failed as an Entrepreneur until I ran out of money. Have to search for a day job again. Will do it all over again.

After going through the different dimensions of the toolkit it was clear to me that I want to quit my job to go all-in entrepreneurship. It gave me the mental clarity I needed, as sometimes decision-making is blurred by unstructured thoughts and unreflected emotions.

One final piece of advice as you face your next significant decision: Look for asymmetric opportunities! If the potential upside significantly outweighs the potential downside, taking the leap is often the right choice. These are the opportunities you don’t want to miss.


Inspiration I used for this article

Books, Podcasts, Articles, Quotes

List of related blog articles from 40 Hour Entrepreneur


Community Space

Your comments, ideas, feedback

  • What's the most significant 'jump' you've taken in your life or career?
  • What role does intuition play in your decision-making process, and how do you balance it with logic and analysis?
  • What other tools or techniques do you find helpful when evaluating life-changing choices?
  • How do you typically deal with the fear of the unknown when facing a big decision?
  • ...

Join the discussion below. Or write me an email to fabiano@40hourentrepreneur.com