February 10, 2016: “Oh man, things are so busy but so exciting…”

February 10, 2015: “Joey and I had a very tense moment today…”

February 13, 2014: “So I started getting into the fundraising grind again and I forgot how fun it is…”

February 10, 2013: “We still haven’t found a programmer…”

Above is a glimpse into four VERY different periods in Chicory’s history, courtesy of my startup journal.

I highly recommend keeping a journal to any first-time entrepreneurs. And not just any journal, but specifically a journal about starting your company.

Aside from the fact that journaling has been scientifically shown to reduce stress and help with sleeplessness, it is incredibly rewarding to see how much you have accomplished over the course of weeks, months, or (hopefully) years. And being able to look back is important because it helps to put into perspective how far you’ve come.

Entrepreneurs tend to be type A personalities. I hear this phrase all the time: “you think that things will get easier when you reach x milestone. But it doesn’t. It only gets harder.” Type A’s strive for the best and it’s sometimes hard to really appreciate all that you’ve accomplished. Keeping a journal means you get to revisit the “you” from 1 year ago and compare the worries and feelings of gratitude you had back then vs now.

Here are some tips that I’ve learned along the way.

Make it fun

It’s easy to let journaling fall by the wayside. People ask me all the time how to get past the first 2 or 3 weeks of journaling. The key is to make your entries fun and insightful. If you can look back on an entry from 3 weeks ago and chuckle or say “oooooh, interesting,” you’ll be more inclined to write in it again.

Make it your own

This journal is going to be 100% for you. Write in a way that you feel comfortable. You could start every entry with, “Dear Startup Journal,” you could draw out entries and make it an illustrated account, or it could even be written as a concise ledger with metrics and financials. It doesn’t matter! Again, the key is that you will find it interesting when you reread it in the future.

Be honest

Entrepreneurs are generally a pretty optimistic bunch, but ask any founder and they will tell you that, despite all the positive thinking, not everything goes according to plan all the time. So don’t just fill your journal with hopes and aspirations; write about what keeps you up at night, what causes you the most stress.

When it comes time to look back at how you spent your past year, you’ll reread your entries and see absolutely fascinating highs and lows!

It’s ok to let your personal life get involved

Running a startup can consume your life. Don’t think that you have to restrict your journal to only things about your company. It’s ok if your personal life gets involved too, because sometimes it’s one in the same.

Use it as a time machine

We all have those days when we think the world is crashing down on us. The journal is perfect for days like these. Go back and read about how you felt when you had successes, and other times that you had failures. You’ll see that things go in waves and in the end, you end up stronger and wiser.

My startup journal is starting to get pretty full. I don’t think the Yuni from September 15, 2012 could have ever dreamed of how far we’ve come today. And regardless of what happens, I can look back on my journal and appreciate everything that has happened to get us this far.

Photo via NVCC

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