Daniel

In early 2019, I felt stuck in my career and took this as an opportunity to reflect on my situation and career prospects. Here, I’m sharing the framework that emerged from this period. I’ve removed personal content so you can directly apply it to your own career.

The framework helps you work through a complex career decision. It guides each critical step along the way, including setting goals for the process, making an assessment of your current situation, getting clear on what a great career looks like for you, coming up with lots of options, collecting data to inform your choice, and making and executing a plan.

That doesn’t mean that the process will be easy. Career choice is cognitively complex and emotionally charged. The problem is ill-defined and resistant to resolution. There’s a good chance that you’ll experience difficult emotions along the way, feel stuck and overwhelmed, under pressure and uninspired.

That’s why having a robust framework is vital. In addition, starting with the right mindset can make a big difference. Here are some suggestions:

1. Get curious: This is an excellent opportunity to learn new things about yourself and the world. Your career is never done or solved. It’s a constant iteration.
2. Have a bias to action: Build your way forward. Accept the situation you’re in right now and find something that’s actionable. Try things until you find what works.
3. Reframe problems: Identify dysfunctional beliefs that keep you stuck, and find more productive re-framings that help you get unstuck and open up new solution spaces.
4. Know it’s a process: Finding your way will take time and involve setbacks. Let go of the end goal and focus on the process and see what happens next.
5. Ask for help: Get support from your social network. The resources are there. People are willing to help you. You just need to ask. 🙂

With that in mind, let’s get started.

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1. Mindsets adapted from the book “Designing Your Life” by Bill Burnett and Dave Evans
2. If you’re interested in career coaching, please get in touch.

In this post, I’m sharing the learning map that I’m using to acquire a strong coaching skill set.

After some deliberation, I decided to pursue the first year as a self-guided learning project instead of getting formal credentials. To set myself up for success, I wanted to get clear at the outset on my motivation to learn, the abilities and knowledge required, as well as the best methods for getting there. Here’s the learning map that I’ve drawn and continue to update along the way.

Reflecting on my first year as a coach, I realized that now was a good time to go through formal coach training. At that point, I had done more than 200 individual coaching sessions and reached product/market fit while still being in the early stages of my development as a coach, where I suspected that training might have the biggest impact. I enrolled in a 6-month program with David B. Peterson, Google’s Director of Executive Coaching and Leadership where I got access to world-class teachings and a community of peers who are significantly more experienced than me.

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For more context on learning maps, I recommend picking up the book “Ultralearning” by Scott H. Young.

Giving others feedback is critical to help them succeed. It’s also really difficult, both for the giver and the receiver. Here are some pointers on how to do well in both roles.

How to give feedback

• Goal: Provide outside perspective and encourage effective future behaviour.
• Step 1: Permission. Ask the Receiver whether you can give them some feedback. This increases the likelihood they’ll change their behaviour. Honour a “no” response. If it’s clearly important, at least give them the choice for when to receive feedback.
  • “Hey, can I give you some feedback?”
  • “When would be a good time for me to give you some feedback?”
• Step 2: Behaviour. Tell the Receiver what they did well or what they did that you would like them to change.
  • “When you (insert behaviour)…” – focus on behaviour, not character
• Step 3: Consequences. State the impact that the behaviour has had.
  • “Here’s what happens: (insert consequences)”
• Step 4: Future. Either ask for a change in behaviour or say thank you for behaviour that you want to encourage. Let the receiver come up with the answer themselves to increase their commitment.
  • “How could you change that?”
  • “Can you do that differently?”
• Step 5: Validation of who people are and of their value to the organization. Also, acknowledge their openness to feedback. It’s possible to do this naturally without sounding too artificial.
  • “It’s great that you took on this assignment. You helped us make rapid progress towards X goal.”
  • “Awesome, thanks a lot!”

When to give feedback

• Ideally, give feedback immediately after you notice the behaviour because the memory will be fresh.
• Solve problems early. Don’t wait until there’s a pattern.
• Pause and reflect before giving feedback:
  • Are you angry? Are you assuming bad intent? If so, hold off for now.
  • Do you want to punish? If so, hold off for now.
  • Can you deliver it with a smile on your face?
  • Should you ask more clarifying questions first?

How to receive feedback

• Be proactive about soliciting feedback so you know how you’re doing and how you could do better. A simple question you can ask is: “How can I do better?”
• How you respond to feedback determines whether you receive more in the future.
• Take the first fall: The best way to do that besides giving great feedback is volunteering to take some as well.
• Pause and ride the immediate wave of defensiveness.
• Move from “that’s wrong” to “tell me more.” Listen carefully. Ask clarifying questions.
• Thank the person for taking the time to help you. Encourage them to keep doing this in the future.
• If you don’t like the way they give feedback, tell them later in a careful way.
• Cultivate a growth identity to respond better to feedback:
  • Love your mistakes. They are your best opportunity to learn and improve.
  • Don’t worry about looking good. Worry about achieving your goal.

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If you’d like to explore these ideas further, here are a few resources that you’ll find useful:

• What Information Do You Need in Order to Change? – Farnam Street
• The Effective Manager – Mark Horstman
• Nonviolent Communication – Marshall B. Rosenberg
• HBR archive on giving feedback – Harvard Business Review
• Stop Softening Tough Feedback – Harvard Business Review
• How Emotionally Intelligent People Give Negative Feedback – Inc.
• How to Provide Great Feedback When You’re Not In Charge – Farnam Street
• Giving and Receiving Feedback – Max Daniel

Cultivating a list of “life principles” can help you discover what you want and how you can align your actions with your values. It enables you to bring your unseen and unquestioned perspectives and ways of being into the open where you can critically examine and change them.

I started working on my own list of life principles in my late teenage years because I noticed a tendency to get washed away by the currents of everyday life. Instead of worrying about what other people thought and what the environment demanded of me, I began to pay closer attention to what I believed and valued. Increasingly, I saw every book and every conversation as an opportunity to gain clarity about my thinking.

However, there was still a large gap between my values and my day-to-day decisions and actions. Cultivating a list of life principles and reviewing them once every week or two helped me narrow that gap. The fact that this list changed a lot over time helped me appreciate that there was probably no point at which I’d have figured it all out, but that I was going to remain a work-in-progress. I’m sharing the current list below.

Looking back, I notice how critical this practice of self-authorship was to my learning and growth in my twenties. It helped me lean into my ambition, cultivate a growth mindset, and become a more effective leader and a better friend, among many things.

And yet, I used to keep this list to myself and not tell anyone about it out of fear of being judged, expecting that others might not be able to appreciate this rather unconventional practice. At this point, I feel comfortable sharing myself more openly, which prompted me to write this post. At the same time, I’ve also become more realistic about the idea of life principles itself, appreciating that life isn’t black or white and that no set of principles will ever do it justice. With that in mind, here’s the list.

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It’s time to stop being vague. If you wish to be an extraordinary person, if you wish to be wise, then you should explicitly identify the kind of person you aspire to become.

Epictetus

Thinking

1. Awareness
   • Pause and attend.
   • Notice that everything is simply appearing.
   • Relax in the midst of struggle and unsatisfactoriness.
   • The quality of your attention determines the quality of your life.
2. Acceptance
   • Dwell in reality and don’t argue with it.
   • Relinquish your reaction to experience by simply noticing it.
   • It’s okay to feel this way right now.
   • Don’t wish to be fulfilled. Instead, welcome all things.
3. Perspective
   • Begin again in each moment.
   • Step away and look at the situation from above.
   • Focus on what you can control. Embrace what you can’t control.
   • It’s not external events that upset you, but your judgment of them.
4. Ego
   • You are nowhere.
   • Let go and become less.
   • Ignore the crowd. Improve your life in relation to yourself, not others.
   • Remember how soon we’re all forgotten.
5. Attachment
   • Everything is impermanent. There’s nothing to hold on to.
   • Don’t cling to ideas. Keep your mind open to what is.
   • Let go of the results of your actions.
   • You are entitled to nothing.
6. Gratitude
   • Enjoy this moment where your consciousness is bright.
   • You will die soon. Let this teach you how to live fully.
   • Compare downwards to feel how lucky you are.
   • Marvel at the universe.
7. Fear
   • Trust in your ability to handle whatever comes your way.
   • Own your fear and lean just beyond it, in every aspect of your life.
   • Choose to be excited rather than afraid.
   • Your life shrinks or expands in proportion to your courage.

Action

1. Resolution
   • Stay true to your principles. Hold the line.
   • Your mission is your priority.
   • Dedicate yourself to quality.
   • Always have a challenge.
2. Ownership
   • Take responsibility for your feelings and needs.
   • Act for the well-being of the whole world.
   • Find a better way.
   • Don’t waste your pain. Learn from it.
3. Resilience
   • Treat setbacks as a test to your ingenuity and resourcefulness.
   • Don’t cling to your comfort.
   • Diversify in everything. Always have a backup.
   • Do what you can, then let things take their course.
4. Adventure
   • Follow your curiosity, wherever you can find it.
   • Treat life as a series of experiments. Do what will teach you the most.
   • There’s no treasure at the end of the process. The process is the treasure.
   • See if you can enjoy this.
5. Transparency
   • In the long run, the truth comes out.
   • Unobstructed self-expression: nothing to hide, nothing to defend.
   • Align what you say with what you think and feel.
   • Seek out games where honesty is the dominant strategy.
6. Connection
   • Live in deep connection with self and others.
   • Treat everyone as family and assume other people like you.
   • Resist envy. Most of life isn’t zero-sum.
   • Don’t give up on people.
7. Execution
   • Action allows you to see the world for what it really is.
   • Let your actions control your emotions.
   • Ideas are worth nothing unless executed.
   • Optimism in the face of uncertainty.

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If you’d like to explore these ideas further, here are a few resources that you’ll find useful:

• Meditations – Marcus Aurelius (Gregory Hays translation)
• Tao Te Ching – Lao-Tzu (Stephen Mitchell translation)
• The Bhagavad Gita (Stephen Mitchell translation)
• Principles – Ray Dalio
• Algorithms to Live By – Brian Christian & Tom Griffiths
• How to Fight a Hydra – Josh Kaufman
• Waking Up – Sam Harris
• Take Ownership of Your Future Self – Harvard Business Review

Coming up with options is one of the critical steps in any decision-making process. Brainstorming is a useful tool to explore the options space. This post illustrates how to do it.

People who have trouble coming up with good ideas, if they’re telling you the truth, will tell you they don’t have very many bad ideas. But people who have plenty of good ideas, if they’re telling the truth, will say they have even more bad ideas. So the goal isn’t to get good ideas; the goal is to get bad ideas. Because once you get enough bad ideas, then some good ones have to show up.

Seth Godin in Tools of Titans

1. Setting the stage

Decide whether you’ll brainstorm on your own or in a group. The latter is preferable since the perspectives of several people typically produce more ideas than any individual on their own.

Next, define the problem for which you aim to generate options, and frame it as a question. Make sure the question is open-ended and provides the appropriate amount of constraint for the brainstorm. Good examples include:

• What are some questions you could ask yourself about [this problem]?
• How many ways can you think of to test [this hypothesis]?

Agree on the rules for the brainstorm. Here are some suggestions:

• Aim for quantity, not quality. Measure the success of the session by the number of options you’ve generated, not the quality of those options.
• Defer judgment. Don’t censor at this stage. Get every idea out on paper. Don’t do anything that would signal liking or disliking of any of the ideas.
• Make sure everyone feels safe to bring up any idea that comes to mind. Encourage wild ideas since they help go beyond the obvious ones.

Finally, decide how much time you’ll dedicate to the brainstorm. Start with a short session (2-4 minutes) to create some urgency, which helps overcome censoring of ideas.

2. Doing the brainstorm

Give everyone a set of post-its and a pen, set a timer, and do the brainstorm. Don’t have the facilitator collect ideas as this limits the speed of the brainstorm.

3. Evaluating the results

Once the timer goes off, collect all post-its in one place. Group similar ideas and give every unique cluster a descriptive name.

Then, vote on the ideas. Do this in silence so everyone can form their independent opinion. Use colored sticker dots to cast votes.

Identify the ideas with the most votes. Discuss their merits and decide what to do about them.

Sample questions

Below are a few questions that have helped me come up with ideas in a variety of situations. Liberally skip any question that doesn’t elicit useful thinking.

• Meta: What are some questions you could ask yourself about this topic? Add those to the list.
• What are the individual steps? Why is each step performed?
• What are the limiting steps? How can you work around them?
• What would this look like if it were easy?
• What metrics can you use to find out if you’re on track? How can you install these metrics in your digital and physical workspace?
• Where does this process need monitoring and gate-keeping?
• What are the worst things that could happen? What could go most wrong? What do you want to avoid?
• What if you did nothing at all?
• What are the second-order effects?
• What are the critical assumptions? How can you verify them?
• Where are you uncertain and expect additional information to be valuable? How can you collect this information?
• Who is an expert at this? How can you get their input?
• What’s the minimum effective dose to get the desired results?
• What would you do to achieve your goal with only 10% of current inputs?
• How can you increase the leverage of your efforts? What do you need to stop doing?
• How can you make yourself redundant?
• What if you could only subtract to solve problems?
• Would you be worried if the details were made public? If yes, why?
• What would your successor do?

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If you’d like to explore these ideas further, here are a few resources you might find useful:

• Better Brainstorming – Harvard Business Review
• Your Best Ideas Are Often Your Last Ideas – Harvard Business Review