A Guide to Finding Your Meaning of Life

The last six months have been a challenging journey for me. I’ve been searching. I’ve been trying to find my unique path in life. I’ve questioned what my calling really is.

Call it being a little lost. Call it a quarter life crisis (a couple years late). Call it whatever you’d like, but for me it has been an incredibly important, personal journey to determine what I should do with my life and finding the next steps to make me truly happy & fulfilled.

This wasn’t something I wanted to talk about (much less write about). However, after yet another conversation with a friend going through the same thing, I realized I really need to share some of the things that helped me get to where I am.

Here’s a few things that really helped me.

1) Read These Books

Everything you’re thinking about has been a challenge for others before. There are experts who have devoted their lives to these subjects and books are a great way to learn from them at your own pace. I read a lot and all of these came highly recommended by friends and mentors, so trust me, they’re helpful.

Mindset by Carol Dweck

Growth means knowing you’re always learning and that even the best were a novice at some point. Never say, “I can’t do that.”  This attitude is an important one to adopt as you find your path: Just because it’s your path, doesn’t mean it will be easy. Mindset will help you understand how to approach the big, scary dreams you have with the right attitude.

So Good They Can’t Ignore You by Cal Newport 

“Find your passion” is the message of Generation Y and I think it’s led many of us astray. There are many things we each are passionate about, but not all of them should be more than a hobby. So Good They Can’t Ignore You will help you figure out what you’re great at and how to do more of it while building a fulfilling life.

Man’s Search for Meaning by Viktor Frankl 

Only 1 in 12 men sent to a concentration camp survived the Holocaust. The author was one of them. From that experience and a lifetime as psychologist, Frankl has some powerful views on life and the importance of having a personal Why. He also reminds us that suffering is a part of life; as much as the American media makes us think we’re all supposed to be happy 24/7, there’s value and growth in struggling with the right things.

2) Find Your Must

I was fortunate to catch Elle Luna’s amazing talk on Finding Your Must when she originally gave her talk in October and am so glad the talk is recorded for all to see. I’ve shared the video with countless friends since. Watch it here: http://vimeo.com/77436516

As you go through those books, it’s important to listen for that voice inside you for what it really wants. In the case of Elle, she was a successful designer at Mailbox (bought by Dropbox), but was having dreams pulling her in another direction.

Just as important is Elle’s awesome article on First Round Capital’s amazing blog called, “What to do at the Crossroads of Should and Must.” This came at the perfect time for me as I was interviewing for jobs I thought I *should* take while working on a startup I felt I *must* work on. I am coincidentally no longer doing the should and focused on the things I feel I must do.

There is a lot of material in the article different than her talk so I encourage you to check out both.

3) Buy a Notebook

This doesn’t have to be anything special. Just get one of those old school spiral-bound notebooks with lots of pages and your favorite writing form (pen, pencil, sharpie, etc).

Start Writing.

Once you have the notebook, sit down alone and start writing anything that comes to mind. Just get everything swimming in your head out and write until you’ve filled a few pages. Do this every day.

What you write about will change. I’ve written about everything from passions to frustrations, forgiveness to regrets, startup ideas to objective views of the past. Every bit of it helped in different ways and brought my mind out of places I was previously stuck.

After awhile you will find you may have less of an urge to write. That’s okay. Know that the notebook is there to release things when they’re stuck inside. It needs an outlet. Don’t bother reading what you’ve written either; some of it won’t be nice things, but there’s a good chance getting it out will help you move on. At least for me, this journey was as much about finding what’s next as it was letting go of things holding me back.

Now, I don’t write in the notebook every day, but when I have something I need to get out of me, I stop what I’m doing and grab the notebook to start writing. I also use it when I’m stuck on something and need to explore an idea. It is this exploration that helped me arrive at what I’m excited to be working on today.

You can learn more about this process here: http://www.dr-jane-bolton.com/support-files/the-artists-way.pdf

4) Read The 12 Week Year

Another book? Yes. The ideas that you’ll be piecing together from the above books, the great stuff from Elle Luna, and writing will make you ready for this book. This is the book that will help you put it all together and figure out how you can really execute on that scary, ambitious *must* that’s dying to get out of you.

The 12 Week Year by Moran & Lennington

On the surface it looks like another pop-self-help book, but it has an important process that will help you clearly define who you want to become and how you can get there.

They ask you who you want to be in 10-20 years, then what you want to be in 3 years to put you on a path to get there, and finally how to find the actionable steps you can take in the next 12 weeks to begin. Following their exercises and examples helped me sew together all the ideas that I had generated from the rest of my journey.

5) Don’t Fear Failure

The first thing you try probably won’t work. Taking the first step to get out the door though is very important. Every thing you try will add new skills, new perspectives, and new people to your life. All of those will combine to bring you closer to your end goal, even if that’s not entirely clear. Don’t be afraid to quit and try something else.

I was an Electrical Engineer in college who realized he didn’t want to be one.  I tried to start a hardware company with some friends (it failed). Then I started Greenhorn Connect, a modest success that gave me a platform for developing skills in marketing, hiring, managing, product and sales. This helped me get jobs first at oneforty (the now-defunct app store for Twitter) and then to move to SF to join KISSmetrics. In both jobs, I learned a ton. Between those two jobs, I tried consulting (the only thing I liked was the money) and a bunch of startup ideas that went nowhere (hint: the moving industry is not a great place to build software).

Most recently, I spent last fall diving into the world of 3D Printing and just never found the right team and idea in the nascent industry. This led me to job hunt again, which is when a lot of the above journey of discovery began.  It was only then that I realized what I really want to do now.

Every step in the journey has been important in helping me get here.  I’ve embraced the fact that this could be another failed step, or the one that puts it all together.

Conclusion

If you really work at it, if you really think about the ideas in the books above and challenge yourself to write what’s in your heart, then I believe you’ll have some things to go on to find the next steps in your uniquely fulfilling life.

I have realized both the good and the bad in my life has taught me important lessons and prepared me for what’s next. In my case, that’s writing a book about How to Build Customer Driven Products based on what I’ve learned from the jobs I’ve had, the consulting I’ve done, and the great mentors I’ve met along the way.  It also means patching up a few relationships I made mistakes with and have much better perspective on now. Most importantly to me, it’s realizing that I’m a founder at heart and that I’m now working on an idea I’m driven to work on every day: helping people be better managers.

I can’t guarantee these tactics will work for you, but working through all of the above and with the help of some great friends I’ve gotten to a satisfying place.  If you’ve asked these questions of yourself before, I’d love to hear what helped you in the comments. This post is for all those coming after us that could use help on figuring out their journey.

Lessons in Innovation from the Biographer of Jobs, Einstein & Franklin

Walter Isaacson has written the biographies for some of the greatest inventors of the last 300 years in Ben Franklin, Steve Jobs and Albert Einstein. He spoke at the National Book Festival in Washington DC and I serendipitously stumbled upon his speech on CSPAN2. It was so amazing, I wanted to share it all with you as I found it is on Youtube here:

I highly encourage you to watch the whole thing, but I wanted to highlight two things that stood out to me.

Simplicity is a spiritual quest.

Especially in the tech scene and product world, we talk about simplicity like a Holy Grail of sorts and with good reason; a truly simple product has many advantages in the market and a strong likelihood of success. I think Isaacson captured this very well in his talk when he said,

Walter Isaacson on Simplicity

Often I find myself getting caught up in building something that is infinitely flexible and covers a million use cases and it makes me forget the essence of what I’m trying to build.

Spirituality comes into play because this requires faith; I have to believe that by sticking to the core of what I’m doing and ignoring some attractive features, I’m building the right product. It also reminds me of the effort required to get there; the first few iterations are unlikely to get to perfection. Instead, it is the dogged pursuit of simplicity that helps find the essence of what I’m really trying to create.

Tying these concepts together, and sharing how Einstein and Franklin thought about simplicity in addition to Jobs is a fascinating insight only the biographer of all 3 could do.

You have to be YOU.

After a question from the audience at the very end of the video, Isaacson covers the most important lesson I think we all need to remember as we read all the tech blogs and study successful people:

“Don’t try to just copy any one of them. Biography is understanding our world, our values and how you might apply them in your life.”

No matter who I’m studying or learning from, I try to see what I should learn from them to build on who I am, not try to be them. I will never pull off the design instincts and asshole of Steve Jobs nor the curiosity and mathematical brilliance of Einstein, but I know I can learn skills and approaches from them that will make the best version of me.

Connecting the Dots: How a Boston Connector Landed at an SF Startup

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”Steve Jobs, Stanford Commencement Speech, May 2005

One of the most common questions I’ve heard over the past few weeks from younger members of our community, especially students, is how to build a career in startups. Unlike climbing the corporate ladder, it’s not a straight forward, linear process. As I just made a major move in my career to join KISSmetrics, I’d like to share how I ended up going from Boston startup connector to SF Product Manager.  This will also help answer questions I know some of you have about how I landed this job.

Connecting the Dots – The unorthodox journey of one startuper

To really begin this story, you have to go back to my days at oneforty. When I joined oneforty, I was given the title of Customer Development Manager and asked to help make oneforty a Lean Startup. Since I had only spent a few months working part time with John Prendergast as his cust dev intern, I really had very little experience. Laura Fitton, oneforty’s founder, took a leap of faith I could learn it, but she also was wise enough to know I could not do it alone.  That’s why she set me up to have mentors from day 1.

Immediately upon starting at oneforty, Laura connected me with two Valley Lean experts she got to know while she was out west raising money for oneforty and Pivotal Labs worked to build V1.0 of the site.  These people were internet mentor legends, Dan Martell and Hiten Shah.  Once a month I seemed to find myself on the phone getting what I would happily call an “ass-kicking” from Dan helping me realize all the things I was doing wrong and most importantly, could do to improve my custdev methods.  Roughly every other month I would have a similar discussion with Hiten.

These discussions were priceless in my career development. I would take copious amounts of notes and seriously reflect upon what Hiten and Dan discussed with me each time. I would also share these notes with Laura to make sure I truly understood them and to force myself to teach someone what I learned (a great tool for deepening your understanding).

A Chance Meeting

Fast forward 12 months at oneforty and it is April 2011. I’ve learned a ton about customer development and lean startups, enough that Trevor Owens, founder of Lean Startup Machine (which was just getting off the ground at the time) invited me to be a mentor at the Lean Startup Machine event in New York City. As destiny/fate/karma would have it, Hiten Shah was also one of the mentors for the weekend.

Being a mentor traveling in from another city is very different from mentoring in your home city. When you’re in your city, you likely only stop by for a brief period of time that fits your schedule. But, when you go to another city, you find you spend the vast majority of your time there…which both Hiten and I did in New York City.

After Saturday’s activities wrapped up, all the mentors went out for drinks.  This turned into an audition and test for me.

With Hiten Shah to my right and Patrick Vlaskovits (co-author of the awesome Lean book at custdev.com) grilling me on all sorts of topics from lean startups, to lessons learned at my first real startup job to topics on psychology and body language.  At the time I was dead set on leaving oneforty to start my own company so all Hiten said was, “if you raise money for your idea, come out west and I’ll give you some intros.”  He also encouraged me to quit ASAP to start doing my own thing if that’s what I was passionate about. Coincidentally I did just that on Monday back in Boston.

Out on my own, but on the Radar

After leaving oneforty, I set out to start my company I’ve always dreamed of.  After spinning my tires for 6 months though, I found myself pretty empty handed and a bit discouraged. After a meeting with Sim Simeonov, I refocused my efforts on the lean startups movement.  After a month of interviews and discussions, I published the results, which caught Hiten’s eye when they were tweeted out.

Hiten DM’d me after my first post and we had a call to discuss my findings, which confirmed his suspicious: Lean as a concept is far ahead of actual solid execution of it in the startup world. At the end of the chat, I mentioned that I was planning a trip out to the Valley in early December and asked if we could meet while I was in town.  He agreed.

Meeting in SF and an Offer

When I met with Hiten in December during my Valley trip, we barely talked about KISSmetrics or my potentially working there. The vast majority of our one hour chat was about my strengths and weaknesses and where I was at in my startup career.

Hiten tried to sell me on the idea that coming to the Valley would solve many of my problems, but I presented a series of challenges that I felt prevented it from being the right decision for me.  He countered I could come work for him and it would resolve many of them. I noted the offer, and it did intrigue me, but it mostly sat just sat in the back of my mind.

By the end of the trip, I was much more interested, thinking it may be the next logical step in my career. On the flight back, I emailed Hiten expressing great interest in the role, especially as I discovered I could potentially be filling the shoes of the departed Cindy Alvarez (who just weeks before my visit had left KISSmetrics to join Yammer).

Getting Serious

With the holidays fast approaching, Hiten and I took things slowly, talking about the the potential first in loose terms then in much more specifics. After one phone call where Hiten lifted the proverbial kimono on everything I wanted to ask regarding KISSmetrics as a business, all that was left was an answer to the question, “When can you come meet more of my team for an interview?

With that, I booked tickets to take a quiet trip to SF for the interview in early February.

Sealing the Deal

With an interview scheduled and a focus on landing this job, I employed my proven job acquisition system that requires me to produce, insightful, valuable content for KISSmetrics.  I happened to be reading a psychology book at the time and so I produced a massive document on different ways KISSmetrics could improve their site based on the principles I found in the book.  I also aggregated all my lean learnings in one place so the rest of the team could see the credibility in Lean that Hiten knew I had.

I wasn’t sure what to expect in the interview. All I had were the names of the people I would be talking to and a vague idea that we’d talk about the KISSmetrics product.  Most of the interview turned out to be focused on implementation: how would you do this, what’s wrong with that, what would you do in this circumstance.

Despite not really preparing for such questions, I was able to crush the interview for one simple reason: the last startup idea I had worked on was a Lean Product Management tool.  While the idea didn’t pan out, it led to me talking to 40 people who run product at companies. Through this, I picked up on many best practices and common mistakes. I was armed with more than enough fodder for the interview and believe I’m really armed to take on my first full time product role.

Conclusion – You Never Know…

Whether it’s lessons learned in a failed startup idea’s customer development interviews or an event you’re randomly invited to in another city, you never know what will lead to the next great opportunity in your career.  Startups are all about embracing serendipity. Embrace the machine and you never know where you’ll end up.

Do you have an example of unrelated events that looking back were instrumental in a step or moment in your career?