2014 Annual Review: A Few (Embarrassingly Personal, Per Usual) Lessons Learned

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Hey everyone, the Annual Review is here!

Note: This is a long post (2,500+ words) and also fairly personal. You have been warned. If you’re new here, be sure to also check out:

OK, let’s get to it! As noted in the process post, I begin the review by focusing on the answers to two questions: What went well this year? and What did not go well?

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What Went Well in 2014

This list includes some of the things I was proud of or that just went well in general this year. In case you get bored with this part, don’t worry—there are plenty of failures and challenges to look forward to in the next section.

Aside from issues of anxiety and sadness (I’ll cover this more in due time), I was in good health for most of the year
I published The Happiness of Pursuit, my first book since The $100 Startup. The book was a New York Times’ bestseller! (Thanks so much, everyone—you made this happen.)

I had a year of good travels, including a return visit to Sydney (my favorite world city), a solo birthday trip to Bali, a trip to Abu Dhabi, and approximately fifteen other countries (I’ll make a full count during the travel roundup, coming in a few days)
I also went on a 40-city tour to meet readers all over the U.S. and Canada in a series of meetups and bookstore events
WDS 2014 was another big success. We brought thousands of people to town. We threw the biggest party we’ve ever produced, which is saying a lot. We began a new series of “Academies” that take place on the days before and after official WDS. And if you haven’t seen this 10-minute film about WDS from an attendee’s perspective, check it out. I’m very proud of our team for making this happen

In addition to WDS, we started another global gathering called Pioneer Nation. The inaugural event brought together 300 entrepreneurs and others pursuing independent work of different kinds. It was a ton of work to put together, but when all was said and done, it was a lot of fun to watch unfold
I gained more confidence as a speaker, traveling to keynote at more than a dozen conferences, events, and companies
I started making wiser choices about spending money to invest in my health and well-being. I finally learned to like green smoothies and green juice (yay). I started taking taxis or Uber to travel around town instead of relying on car-sharing or public transport, frequently saving time and frustration
Working with a small (yet mighty) team, I published four new Unconventional Guides: Freelance Writing, Designed to Sell, Get Rich Slowly, and Upgrade Unlocked
Having previously expressed that I was frustrated in my declining track record of financial giving, this year I did a better job. I gave more intentionally and frequently to organizations that are doing worthy work
I worked with a wonderful design studio to reboot this blog. Since we debuted the new design and format in June, I’ve published posts almost every day. I’m especially psyched about our Profiles series, which highlights readers who are exploring interesting ideas, pursuing big goals, or otherwise living unconventionally. The new format has been great, and I’m looking forward to continuing to refine it in 2015
I recently signed a deal for my next book, which I’m really excited about. I’ll be working with a new editor for the first time in four years, and both of us are energized over the concept and outline. (As part of a crazy experiment, this time I’ll actually write an outline before I start writing the manuscript—but more on that another time. And I’ll tell you what the book is about another time, too. First things first.)

A Note Before We Continue

As promised, I’m going to share some real failures and truly difficult things about this year. But first, here’s another confession: when I started the process of writing everything down, I was worried. The heaviness and negative feelings I’m about to describe have been weighing on me so much lately that I had almost convinced myself that the whole year was a bust.

But no! Once I started reviewing my calendar and writing down these highlights, I was amazed to see so many good things crop up that I had totally forgotten about.

It reminded me of one of the core lessons of the Annual Review: we tend to overestimate what we can accomplish in a single day, but underestimate what we can accomplish in a full year. For that, I’m grateful.

What Did Not Go Well in 2014

OK, no need to run from it—the list of things that did not go well is not short. This list is somewhat abridged, but you’ll probably get the gist.

Overall, I experienced a high amount of sadness, anxiety, angst, and inability to focus. For many days in 2014, I felt “on edge” for large parts of the day. I walked around with the constant sense of being distracted or even fearful. These negative emotions and impacts occurred off and on throughout the year, but culminated to an especially loud pitch in the past few months
I was constantly in a state of being behind on everything. For years I’ve prided myself on working quickly and over-delivering. But lately, I’ve been late—over and over. I was late in delivering my book manuscript, which caused my publisher to delay publication of the new book from Spring to Fall. I was late in working with several trusted and competent business partners (sorry, guys!). I was even frequently late to appointments, a bad habit I’ve never indulged in before
It’s more than just being late: I’ve often felt that I’m letting down everyone who is close to me. My family, my friends, readers, colleagues, and the community I seek to serve… pretty much everyone. It’s not a great feeling
The book launch for The Happiness of Pursuit was good but not amazing. Sure, we started well and hit NYT, but overall, the long-term sales for the previous book are much higher
Similarly, the Unconventional Guides launches and other business projects were good but not amazing. (The point: we need some amazing around here! Reasonable people might settle for good, but I am not reasonable.)
Speaking of books, I stopped reading them. Well, I didn’t stop—but I used to pride myself on reading at least 50 books a year. This year, I probably read 25-30 at most. I worry that this loss of learning relates to a loss of creating, for learning is critical for both personal growth and writing. “If you want to write, read more books” goes the old advice, and it’s good advice. But somehow I got off track with this, too
I often failed to appreciate my circumstances. I did not maximize my units of momentary happiness. Sometimes I’d be in a beautiful setting or otherwise be experiencing something very privileged, like flying First Class or staying in a nice hotel, and I’d still feel sad. Then I’d feel guilty for feeling sad, and I started to have the sense that it was all meaningless
I did not always provide good leadership for the people who contribute their valuable time and energy to our group projects. In particular, doing two major events (WDS + Pioneer Nation) with largely the same team in a short period of time was a big challenge
In the midst of another difficult time in dealing with a family situation that was far away, I received the worst text message of my life while preparing to sign books at an event in California. The confluence of these events, which also happened at the same time I was trying to make a big decision about my future in publishing (when it rains, it pours!) produced the most difficult 60-day period of any recent memory
I don’t have many close friendships (and I’m generally comfortable with that), but lately I’ve sensed that the ones I do have are becoming strained or at least somewhat distant
Throughout the year, my elderly grandmother became more confused. Two months ago she became suddenly ill and died shortly after being hospitalized (here’s my tribute to her—thanks for all your kind comments)

As I said, this list is somewhat abridged. But I know it’s intense.

Does everything happen for a reason? I certainly don’t think so, though it’s interesting to consider why we might place certain events in the movie of our life.

I also don’t believe that every cloud has a silver lining. There are plenty of “clouds” in our life that are just undesirable and unwelcome. Nevertheless, in reflecting on this list of negatives, I do notice a few positive interactions or by-products.

For example, I was very sad when my nana passed away, as almost anyone would be. But I was also relieved that she died in relative peace. At the hospital, right before her symptoms were treated with morphine, she said she was “ready to check out.” She was 88 and had lived a wonderful life.

Even though I haven’t always been the most reliable family member, in the months before her death I traveled home twice and had good experiences with her and everyone else who was involved in the situation. If I hadn’t done that, I think I’d feel a lot worse.

In other news, the fact that I had such anxiety and inability to focus led me to recently seek therapy and even medical help for the first time. I’ll tell the whole story about this in an upcoming post, including an unexpected and partial solution I found through the process. But for now, in general I think it’s a good thing that I took this drastic step. I’ve been struggling for a long time, but until the situation became more severe, I continued to attempt to handle everything myself, with only mixed results.

Lastly, because I know I am goal-oriented and always will be, I’m glad that I was still able to do a lot despite all these problems! As mentioned earlier, I had the depressing things in mind as I began this review, so I was almost prepared to say, “Yeah, this year was just terrible through and through.” But again, that wasn’t the case and there were still a lot of highlights.

It was just a challenging year in general, and most of us tend to accentuate the negative over the positive. I still have a long way to go in this overall exercise, but the Annual Review process has been helpful in reminding me that our lives are multi-faceted and complex.

For years I’ve said I’m a “realistic optimist.” I try not to be naive but I do have hope. I will always have hope.

Lessons from the Journey

I’ve tried to be as honest as possible in compiling the above lists for anyone who cares. There are probably some obvious lessons that run throughout, and as I’ve been processing all of this, here are a few that I take from it.

Gratitude and happiness are not the same thing. When I first started journaling my notes for the review, I made the mistake of saying that I haven’t felt very grateful lately, but this was imprecise.

I can honestly say that while I’ve been sad and anxious, I’ve lived with gratitude more often than not this year, and that feels good. As Jason Mraz said once, you can be successful and still experience melancholy. If I struggle, I can still have a good life—and presumably, you can too. I do have a good life and I will continue to be grateful, regardless of external circumstances or even my own failures.

That said, I need more units of momentary happiness. One of the scariest things for me was realizing that I have a hard time identifying these moments in my life. When I look back and think of things that made me happy this year, I find them colored by something negative. I don’t know how to change this, but one way or another, I need to take more joy in present surroundings, once again regardless of any perceived negative circumstances.

What doesn’t kill you at first will probably try again. I’m not sure of the origin of this phrase, but I read it recently and immediately related to it. It’s a sad lesson, sure, but presumably a helpful one for some of us. (See also: Stockholm Syndrome.)

I must continue to recognize the cost of doing small things. I recently summarized Greg McKeown’s rule of only saying yes to ideas that are at least 90 out of 100. I’m generally resistant to this sort of philosophy in general, for a lot of reasons. I believe our lives are too complex to reduce to mere machine-like efficiency, and as noted, we can accomplish a lot more in a year than we tend to believe.

But like a lot of aphorisms, perhaps the best answers depend on the context and seasons of our lives. Regardless, I need to be more specific and intentional. Life is too short and the potential for greatness is… far too great to ignore.

Ensure that goals are closely aligned with your overall vision. This probably sounds basic, but anyone else who is goal-oriented and future-minded may need to hear it. At the beginning of this year I chose “Relationships” as the theme, yet I felt sad and even unsuccessful in strengthening the ones that matter most, and also in navigating situations that felt unfamiliar and uncomfortable.

If I want to prioritize commitments to friends and family more, I can’t just wish it to happen as I continue to spend all my best time working on everything else that matters to me. Also, a theme of “Relationships” is far too general. As with any other goal, specificity and a clear definition of success are critical in seeing it through.

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Your Turn (If You’d Like)

Well, this has been a long post—and there’s more to come about several of these points. In the next few posts, I’ll share more detailed lessons from this year, including a full post on Business & Work lessons, a Travel Roundup, and … dun, dun, dun … a detailed post on what’s to come next year. Whoa.

If you’ve read this far, thanks for your indulgence. Some of you have been around for years, and you are the reason I make these posts public. It’s my strongest hope that something I share will be useful to you as you plan your own life and goals.

Speaking of that, how about you? How was your year?

All Annual Review posts this week will be open for reader comments, and you don’t have to write 2,500 words like I just did. Just give us a few highlights in response to these questions:

What went well in 2014?
What did not go well in 2014?

And remember, if you write a post of your own, link to one of these posts and include the hashtag #AnnualReview. I’ll include as many as possible in a future roundup.

Comments here.

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Image: Untrained Eye, Herr Olsen