Keep a Daily Journal to Spark Your Second-Act Career

Even if it’s been a long time (or you’ve never done it) writing a daily journal is the best way to begin workshopping your second-act career transition.

Indeed, high school may have been the last time that you kept a regular daily journal. For as long as there have been writers, there have been journal keepers. Journals or diaries come in many forms. We’re most familiar with the confessional diary that chronicles our daily thoughts and tries to make sense of the ups and downs we experience in life. This is not that diary!

What’s Different About this Journal

The style of this daily journal is very spontaneous and unplanned. The goal is to capture what is coming up for you at the moment you’re writing, not to summarize or narrate or download what is going on in your life. This allows you to develop a more direct channel to the part of your mind that is just below your radar. This is the part of you that really knows what you want and what you need to begin planning and re-thinking your career.

No one else is going to be reading it. You don’t even have to read it or re-read it after you’ve written an entry. It’s an exercise in releasing thoughts and thought patterns that are embedded within your consciousness. These patterns may be blocking your clarity around your career options or plans.

After all this time on the planet, working and living for decades, we’ve all acquired a certain amount of baggage. I talk a lot about this in my practice: to create the future, we have to reconcile the past.

The daily journal is one place where we can bring up, observe, and dissolve some of the old thoughts, judgments, or beliefs that no longer work for us.

By tapping into our deeper mental and emotional levels through the regular journal entries, we can begin to clarify and dissipate some of these old patterns that may still be holding us back. We may now be able to see things differently. We’ll be able to see pathways forward where we previously felt blocked.

Don’t censor yourself or stop yourself from writing down the thought or feeling that you’re experiencing as you write. Free yourself to go to places you don’t normally go to in other writing or your conversations with people. This is your private space, so don’t hold back. There’s actually no need for you to keep what you’ve written. Once you’re done, you can tear out and throw away the pages. You can also burn them to dissipate the energy behind the words you’ve just written (if you believe in that idea).

Write in Longhand

There are very few rules for this journal. But please follow this one. Don’t type your journal on a keyboard. Use a pen and a dedicated notebook. My favorite is the 8.5 x 5.5 inch Moleskine hardbound notebook. It’s the perfect format to hold comfortably in your hand. I find that writing a single-page entry (my daily prescription) takes between 10 – 20 minutes, depending on how focused and inspired I am.

There’s something magical and mystical about writing longhand. It opens up a direct communication channel between your conscious and unconscious mind. It taps into the deeper reservoir of ideas that you may not be aware of in your daily life. By writing your daily journal, you strengthen this channel and create an ongoing outlet for your inner inspiration and wisdom to come forward.

Follow the Thread

Don’t worry about what you’re going to write about. Just open to a blank page and write whatever is on your mind in that moment. Write the stream of consciousness that you’re hearing in your mind. You’ll get the most benefit by planning less, and just following whatever words or ideas come into your head. Just dive into the river of your own mind, and follow the current wherever it takes you.

People always ask me:”What happens if I have nothing to say?”

This is entirely normal and expected and happens to me all the time.

This process helps you connect to the flow of ideas, emotions, memories, and other thoughts that are lurking or hidden below your conscious mind. As you write, the action pattern of forming the letters and words on the page pulls your attention away from your conscious mind that will want to control and censor what you write.

You’ll hear all sorts of resistance coming up: “Oh, this isn’t important.” “This feels silly.” “Why am I writing this nonsense?” Or you’ll feel completely stuck, your mind a complete blank.

Keep going. Keep writing the nonsense until your conscious censor runs out of steam and you start to hear other thoughts. Or just make something up. Write about what you’re feeling in that moment. Maybe you’re feeling angry that you agreed to write in this journal in the first place. Maybe you’re angry at me for giving you the idea. That’s OK. Go with it. Let yourself scribble off the end of the page in frustration if it makes you feel good. Write nonsense, baby talk, silly song lyrics.

This will distract your conscious mind, and very soon you’ll find that your deeper thoughts are now able to bypass your conscious censor. When they are ready to reveal themselves, they will pop into your mind as you’re writing, and you can pluck them out of the air and capture them on paper.

This may sound like a metaphysical process, and I agree. It is.

I guarantee you that if you persist through the resistance and the blocks, ideas worth writing about will pop into your head and you’ll be off on an interesting and valuable topic.

Where This Connects to Your Career

Unlike your high school diary, this daily journal is part of your career plan. It is an opportunity to surface, ponder, and workshop many aspects of the career transition you are either contemplating or acting on.

If your career plan is among your top life concerns, or the number one concern, then you will be naturally accessing the inner thoughts, resources, ideas, or solutions that your deeper self knows you need. Don’t worry about having to push yourself to come up with relevant insights. Just relax, listen for them, and they will appear.

I believe that there is an inner knowing inside your mind. On some level, you are already pretty clear on what your second-act career should look like. Each of us is different, and it’s going to manifest differently for you than it does for me. But this process can put you in touch with that inner knowing.

This is going to work differently for everyone. There is no set way this should work. Your mileage will vary.

So your journal could be a place where you very quickly begin to capture and flesh-out specific ideas for your new job or business. You could be very inductive about it and work out all of the details, from job description to your salary negotiation, to recruiting a team.

You could also start from a place of knowing absolutely nothing about what you want to do or where you’re going. In this instance, I would recommend that you focus on the present moment each day. What are you feeling right now? What is bugging you or inspiring you today? Be very open and free-form (stream of consciousness) about it. Don’t look for or expect immediate results. Use the present focus as a way of discovering issues that may be keeping you from finding your inspiration.

Random Thoughts Become Actionable Ideas

In this iterative approach, over time, you may find that certain ideas or patterns begin to emerge in your writing. Maybe ideas emerge for a job, a business, a role, or a mission and begin to gain traction for you. See how you feel about them each day, and start to riff about them. Explore different aspects. Imagine yourself in this new role or activity. Imagine the impact or effect of your work in this new role. Dare to believe it.

Many of these ideas will be actionable and you may want to track them or implement them. You won’t want to have to search through your scribbled pages later trying to find those patterns. Instead, keep a pad of post-its in the back of your journal and use them to capture these actionable ideas you’re going to want to remember later.

The Value of Consistency

No matter which approach or direction your journal takes, or what value emerges from your pages, the most important thing about it is to stick with it. Every day. Don’t miss a day (please try).

Checking your journal off your to-do list every day helps you build trust in yourself. Perhaps that sounds weird. You’re thinking that this is such a small thing. How can writing a page a day help me trust myself?

We’ve learned a lot about behavioral science over the last twenty years, and there have been some great books in recent years about habit-building (most recently James Clear’s Atomic Habits, and Charles Duhigg’s The Power of Habit). What the experts are telling us is that repetition and consistency are powerful transformational practices.

So by writing a page a day in your journal, you are sending the message to your consciousness that you are committed to supporting yourself on this career transition journey. Your willingness to make this a priority, and to show up for yourself through this commitment, will give you the confidence to be able to show up for others.

Ultimately, if you are looking to restore the confidence you have lost through losing a job, or losing your way in your current job, your journal is a great way to build yourself back up.

Best Times to Write in Your Journal

Make sure to write your journal page all in one sitting. For me, the best time is in the early morning, over a cup of coffee when the house is still quiet and my mind is still contemplative after having just woken up. I don’t know about you, but I often wake up with a sense of clarity about what I have to do that day, or a sense of perspective about life. It wasn’t always that way, however. After I left DreamWorks Animation at the end of 2009 in the middle of the Recession and at the tail end of a divorce, I would often wake up in a cold sweat, panicking about the day ahead.

In either situation, whether clear or afraid, picking up the daily journal is and was the productive choice.

From the positive place, I’m able to let my mind flow freely and can address a problem or a task or a project I need to do. I can re-prioritize my agenda, or make decisions about what I’m going to get done that day. The unexpected deeper thoughts seem to flow more freely in the quiet setting, before the busy-ness of the day crowds them out.

From the negative place, the daily journal can be a refuge. It’s the outlet for all of the nightmarish thoughts that come up for all of us when we are in a state of transition and loss. When we feel like the uncertainty or the loss are overwhelming, expressing those feelings in the journal will get them out of the way and allow the support and wisdom to come forward.

So even in the negative place, the journal serves exactly the same purpose it does when I’m in a more positive place. It helps me calm down. By writing out all of the fears (acronym: False Expectations Appearing Real), I can gain some perspective and realize that I do have options. I see that there are things I can do. I realize that I am empowered to make a plan and act on it.

This whole process also works if you write the daily journal at night before you go to bed. That’s another quiet time to be alone with yourself and your mind and your page. Look ahead to the next day and decide how you’re going to live it. Release the concerns that you’ve been holding onto from the day and give yourself the opportunity to come back into a greater sense of balance and perspective. You’ll probably get to sleep faster and sleep better because you’ve unburdened yourself of what was weighing you down from the day, and your mind can look forward to the next day with a refreshed sense of what’s possible.

Set a Clear Intention

In my Boomer Reinvention book, I called this the “reinvention journal.” It still very much serves that purpose: to help you redefine and reinvent yourself in this second-act career transition. It can help you awaken to the idea that you have many more years of valuable and rewarding work left in you. It can help you maintain a regular check-in to monitor and reflect on the progress you’re making towards your career goal.

But over the past few years, I’ve added an additional element, which is why I’m now calling this the “intention journal.”

I’m finding that it is helpful to set a clear intention somewhere in each daily entry.

That intention can be as specific as finishing some kind of project or milestone, practicing your elevator pitch, building your network, or scheduling an important call or meeting. It can also be more about the way you want to be over the course of that day. Maybe you want to set an intention to listen more carefully to those around you. Maybe you want to set an intention to take more breaks during the day to refresh and recharge yourself. It could even be something as simple as setting the intention to smile more often or to listen to your favorite song or album.

Whatever intention you choose, it is one more little trick to help you stay more present. And staying more present will help you stay on track with what is really important in your life right now.

It’s another opportunity to make and to honor a commitment to yourself that will build your confidence and make you even more accountable to yourself.

The 32-Day Challenge

Are you up for a challenge? Try journaling once a day, every day without missing a day, for 32 days.

32 days is a convenient target because it maps to an average number of days many behaviorists believe can lock in a new habit. So if you journal for 32 days without missing a day, you are really anchoring into your unconscious this idea that you are trustworthy, reliable, and consistent. This will prove to you that you can keep your commitment to yourself. And if you can keep to your own commitment, that will make it easier and more believable when you walk into a job interview and pledge your willingness to commit to that prospective job.

Look at the flip side of this. How do you feel when you give up on a New Year’s resolution? Or any other commitment that you make to change your behavior? Writing for 10 minutes in a journal is a lot more attainable than the ambitious resolutions you may have attempted in the past. The point is that when you’re looking to transition to a new job, or kick your career up a notch, or begin the arduous process of planning out your career for the next few decades, you want to believe in yourself, and believe you can do it.

Journaling is the little match that can light up that very big and bright future.

Set Reasonable Expectations

Journaling is not a competitive sport. Please don’t mistake my challenge as some kind of mental/emotional boot camp.

In building my journaling practice, it took me a very long time to complete a 32 day streak. If you don’t make it to 32 days, it doesn’t mean that you aren’t committed to your plan or to your future. It doesn’t mean that you’ll blow your next job interview.

This is a process. Be supportive and understanding and compassionate about it. Yes: set a goal, set an intention that you’ll engage fully with the daily journal. But then let the chips fall where they may. If you miss a day or a week, just pick it back up. Over time, you’ll find the value of it. Maybe you’ll journal religiously for a week or two but then stop. Maybe you’re not feeling it. But then a month later, you’ll be in the midst of some new project, or you’ve met someone who’s interested in hiring you – whatever. And you decide to pick the journal process back up.

Let it unfold for you at your own pace and use it as a support mechanism, not as a cudgel to beat yourself up for what you’re not doing.

Explore it. It’s just another tool. Use it if it works for you. Timing is also important. It may not work for you right now, but it could be immensely valuable at some point in the future. So be open to it, and know that it’s a technique that is available to you whenever you need it and can benefit from it.

Let me know your thoughts, questions, or experiences with the journaling process in the comments below!