A worksheet from my talk “DRI Your Career”. Rough, honest answers are more useful than polished, careful ones.

The most important thing is to define your proximate objective: your next achievable goal that builds the kind of career (and life!) you want. It’s an experiment, not a commitment. If you try it and learn it’s not for you, that is still progress!

A good proximate objective:

• Challenges you, but feels possible
• Teaches you something, so even if you fail, you learn something
• Is something you want to do
• Is within your control

1. Where you’re at

It’s completely normal to not be up for a challenge 100% of the time. Think about where you’re at right now, honestly.

• Are you up for a big challenge?
• Do you really value stability?
• Do you need some rest?
• What are your constraints? Write them down, and discuss them with someone you trust.

2. The What

This should be specific enough that you know when you’ve achieved it, but broad enough that reaching for it demonstrates a genuine expansion of your capabilities.

• How will you know you’ve done it?
• Is it in your control, or is it something someone else has to give you? (“Get promoted” is not in your control)
• What will you learn, even if it doesn’t work out?
• Is it small enough to be doable, and big enough to reveal something meaningful?
• When will you check in on what you’ve learned? Pick a date, 3–6 months out.

3. Why

Your underlying motivation, and a critical counterpoint to the what. When you read it, the why should remind you why it’s worth the struggle and the work to take on the what.

• Why does this matter to you?
• Is it something you want, or something you think you should want?
• When it gets hard, what will remind you it’s worth it?

4. Resources

What you have available to help you achieve it.

• What time can you realistically give it?
• What can you learn from: books, courses, people who’ve done it?
• Is there work you’re already doing that could move this forward?

5. Support

It’s unrealistic to get all your needs met by one person. Build your raccoon squad.

• Who supports you now? Think manager, skip level, peers, mentors, sponsors, coaches, work BFF.
• What’s missing? For example: “I don’t have anyone who challenges my thinking”, “I don’t have someone senior who can help open doors”, “I don’t have peers outside my company”.
• What’s one thing you’ll do in the next month to strengthen your support network?

6. Opportunities

Opportunities are like flowers. Sometimes people give us flowers, sometimes we pick flowers, and if we want to have flowers later, we better start planting them now.

• What do you actually like doing?
• What can you plant now that will pay off later?
• What’s already within reach that you could pick?
• When someone asks you for something you’re not sure about, is it an opportunity to negotiate?

Bonus: Have Claude hold you to it

Claude isn’t a substitute for coaching, but it’s useful as a self-accountability loop. You can use a Claude project for this.

I'm working on a career goal and I want help holding myself to it.

Be direct. Push me to be truthful with myself. Don't be overly positive.

Ask for my plan or walk through the steps at https://cate.blog/career-goals-worksheet/

Check my goal against these criteria and tell me plainly

where it falls short:

- It challenges me, but feels possible

- I'll learn something doing it, even if I fail

- I actually want to do it

- It's within my control, not something someone else has to give me

- The what is specific enough that I'll know when I've done it

- The why would remind me it's worth the struggle

- It fits where I'm at right now and my constraints

If it falls short, ask me questions to help me rewrite it.

Don't rewrite it for me.

Once the goal holds up, help me break it into steps for the next month. Those steps should be tractable within the time I have for it. Make sure I have concrete, recorded actions that I'm tracking in my usual planning system.

Help me build a way to keep track of this using my usual systems. If I don't have usual systems, build them. Set a cadence to check in and then compare what I've done against the plan using what I tell you, not how I feel about it. Tell me what moved, what didn't, and ask what I can learn. If I keep missing the same step, say so, and ask whether the goal or the plan needs to change.

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