RE: Creating a Personal Development Checklist

Here’s a list of this community’s personal development suggestions. As a reminder, this list is meant to inspire people who want to own their development but don’t know where to start or don’t know what to do next.


Set goals that are specific, measurable, achievable, relevant and time-bound. Ask yourself, What do I want to achieve? These achievements could be personal or work-related. Do you want to learn how to be a manager? Do you want to help kids learn to play music? Do you want to improve your health? Do you want financial freedom? Do you want to make a positive impact on your community? Identify a near-term ambition and aim for it. Then ask yourself, At the end of this week or month, what goals will I set to make progress toward my ambition? Here are some examples of goals:

  • I will read a book about effective writing and communication this month.
  • I will volunteer to help the local music teacher every Friday.
  • I will walk one mile every day this week and only drink alcohol on Friday and Saturday.
  • This month, I will start a mutual fund and add $300 to it every 30 days.
  • I will raise $500 for a local food bank before April 1st.

In your fields of interest, identify the books that people you respect swear by. Read those books. Set a goal to read one book every sixty or ninety days. If you prefer the community aspect of reading, join a book club. Spend 1–2 hours a week reading and you’ll likely meet this goal with ease. If you start reading a book and it doesn’t resonate with you—maybe it’s boring or too dense—put it down and start reading a different book. Repeat until you find a book that is a page-turner. Once you finish that book, start the process all over again. To read is to see the world through another person’s eyes. There’s always something to be gained from that. (If you prefer to listen to books, do that. Just don’t multitask while you do. You cannot multitask. If it’s any consolation, neither can I.)

Find a mentor. (More info here)

Find a peer that you share interests with. Spend time with them every month, or more. Ask them what they are learning. Tell them where you are struggling and ask if they have encountered similar challenges. Use the time to talk about your careers and your aspirations. Use the relationship to hold one another accountable to your goals.

Find a mentee. Ideally, this someone with a different background than you. Commit to spending at least an hour per month with them. You might already know someone who would make a great mentee. If you don’t, call your local school district to inquire about local mentorship programs.

Keep an informal journal of things you are learning, things you are proud of or grateful for, things you wish you’d done differently, things that are difficult right now, or things you are excited about. It’s okay if you don’t write in it every day. It’s okay if some days you only write a sentence or two. Just be sure to date each entry whenever you write something down. The point of your journal is to capture your thought processes and ideas, so you can go back to them at a later date and see IN WRITING how much you’ve grown. Writing is a great way to process life events. You don’t ever have to share your writing. Just make a habit of writing more. Here’s my friend Mitch on journaling: “As I’ve journaled through the years, I’ve developed a ton by understanding where I’m at, where I’m struggling, and how I want to make progress.”

Have that difficult conversation you’ve been meaning to have with your boss, teammate, friend, or spouse. Every difficult conversation is an opportunity for personal and relational growth. Use the conversations to better understand the other person, their goals, and their needs—and to help them better understand you, your goals, and your needs. (Read Nonviolent Communication to learn how to have difficult conversations that work.)

Stay in contact with the important people in your network. Make a list of 20–25 people that are important to your career and personal well-being and contact them once every ninety days or so. Ask them what they are learning. Ask them what they are excited about. Ask them how they are doing. Send them a book or an article you enjoyed and tell them why you enjoyed it. Be genuinely interested in their lives, especially if you want them to be genuinely interested in yours.

Sign up for daily emails that relate to your aspirations and goals. For example, if you want to be a manager, sign up for Harvard Business Review’s Management Tip of the Day and read what they send you. Treat the advice—and anyone’s advice, for that matter—as a data point, not gospel.

Consider working with a local nonprofit. It will be challenging and, ideally, rewarding. It will also help you develop your skills. As my teammate Brian says, “Earlier in my career, I sat on a nonprofit board and it helped me gain experience at a level that I didn’t have access to in my current job.” Like Brian, you might be able to sit on an advisory board and learn something about management or leadership. Alternatively, you might be able to help a nonprofit with their website, their outreach efforts, or their operations. The possibilities are endless. If the first nonprofit you find isn’t for you, find another one.

Self-assess. Use assessments like the Enneagram, Advisa’s Predictive Index, Myers-Briggs, or Strengths Finder to help you understand your natural drives, behaviors, and strengths.

Ask others to assess you. Ask your manager pointed questions about what they love about the way you work—and what they don’t. Ask your friends, your peers, and your mentors what they think you are good at. Tell them you are asking because you are trying to build on your natural strengths. Then, take their feedback and identify one thing you want to get better at and work hard at it. Read as much as you can about the topic. Find people who are good at it and ask them how they learned to do it, or what advice they’d offer people who want to improve at it. Then, find ways to practice. For example, maybe you want to improve your presentation skills. Try signing up for an event that will force you to present in front of a crowd.

Please note: I do not recommend doing all of these things at once. My recommendation is to pick one thing at a time and focus on doing it well. Development takes time. Start somewhere and commit. And be sure to celebrate as you make progress—I’d love to hear about your success.

— Max


This is Max’s note—a weekly message from Lessonly’s CEO about learning, leadership, and doing Better Work. Sign up below to subscribe via email. No spam, we promise!

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