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.


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.

How to Plan for Succession in Your Business

Whether you’re building a volunteer organization, a high growth business or a profitable side project, there is likely going to come a day when you no longer will be able to (or want to) run it.  Building something that outlasts your direct efforts is a real accomplishment, but few talk about how to actually do it.

As I just moved to San Francisco, I’ve gone through the process of succession for my role in Boston running Greenhorn Connect, a site that aggregates everything going on in the Boston startup scene.  (You obviously can’t run the day to day of such a site from another city.)

I’ve been fortunate enough to find someone great, Paul Hlatky, to take over and even managed to get my awesome team on board with the idea. This was no mistake. I was fortunate to have been able to solicit advice from some of Boston’s best leaders. I’d like to share what I learned from them and in the process of handling this succession.

Special thanks in particular to Tim Rowe of the Cambridge Innovation Center and Michael Skok of North Bridge Venture Partners for their advice for this post.

How to Handle Succession Planning for Your Organization

1) Start planning before you need a successor.

In October 2011, I talked with my team at our monthly Greenhorn Team meeting about the idea of me not always running the day to day of Greenhorn Connect. After 2 full years, it seemed like it would make sense for someone new to give Greenhorn Connect a fresh injection of energy and vision. At the same time, I was trying to launch a company, so I realized that a founder of a growing business would not have the time for a side project like GHC.

From that meeting forward, I started quietly keeping an eye out for a successor and thinking about what it would take to hand off the business. This led me to ask myself a few key questions:

  • What are the core benefits to the job I can sell someone on?
  • What is the archetype for the person & skills needed for this role?
  • What role would I expect to have after the transition?
  • What don’t I know about succession planning that I should learn about?

At the outset, I had few answers, but it gave me a framework to get started on the process before I needed my successor. It also helped me understand what questions to ask others when I had the opportunity to learn how they’d approach the challenges I felt were coming.

2) Be proactive and seek out your sucessor.

Once I realized the kind of person I was looking for was going to be a hungry student new to our ecosystem and hungry to help others that were new to the ecosystem, I needed to find some leads. By narrowing the definition of who I was looking for I was able to concentrate my search to a few student leaders starting to emerge in the community.  Since I didn’t want succession to be done in the spotlight, I had to seek them out directly and somewhat discretely.

Paul, then a senior at BU, had attended our massive conference the unconference and wrote a passionate blog post about connecting students. It came across my Twitter stream one night and I followed up with him by commenting and then meeting up with him for coffee.

3) Try before you buy.

Successions that fail don’t end well for anyone. Just ask John Sculley (aka- Jobs’s disastrous first successor). To save embarrassment for you and your potential successor, the best thing you can do is try before you buy. This means working with them and spending a lot of time with them to make sure you feel comfortable with them taking over.

For Paul and I, this trial ended up turning into a jointly organized Startup Career Fair. Pulling off a major event like this (500+ students and over 30 companies) requires a great deal of coordination and help. Paul showed incredibly skill as he recruited dozens of students to help, negotiated huge discounts from our venue and otherwise showed great business instincts. Even before the fair occurred I knew I had the right person, so I made the pitch.

4) Sell the Dream.

No matter how ugly, everyone loves their own baby. But if you’re handing it off to someone else, you have to convince them to love your baby, too.  Once you’re certain you’ve found the right person, you need to grab a pair of rose colored glasses and sell the dream of why this person should want to take over for you.

While I knew Paul was a great young hustler, I didn’t know everything about his motivations yet, so when I made the pitch, I laid out all the benefits I knew Greenhorn Connect could provide its leader. I focused on what I knew motivated me to do it as well as some of the things that were cool, ancillary benefits of the role.

If you’re stuck on what to say, just think about how Willy Wonka made it impossible for Charlie to pass on the opportunity to run the chocolate factory…and reveals much of his succession plans:

(Quite possibly the best “Sell the Dream” ever. Skip to 3:03 in the video)

5) Focus on values and key success factors.

When you choose a successor, you have to realize they are not you. You can’t expect them to do everything as you have done it before. Instead, you need to focus on instilling the core values of the role and what matters most to the success of the business or organization. These values and key success factors will act as guide posts for your organization’s new leader to make their own decisions by.

In the case of Greenhorn Connect, I shared a large Google Doc with Paul filled with insights to what I felt had made the site a success to date and things I felt were our core strengths and weaknesses.  I also shared with him many of the processes and productivity hacks I had used to run the site, but I tried to emphasize that he was welcome to come up with new strategies and tactics as long as they didn’t compromise our core values.

With what I’ve seen in Paul’s first 3 months running GHC, I can see that he learned the values and is now bringing some of his own style and ideas to the table, making Greenhorn Connect better than it was before.

6) Put them out in front.

Now that you’ve got your successor excited about the role and are instilling your values in them, it’s time to shine the spotlight on them.  When I asked Tim Rowe for advice on succession he had a lot to say about this in particular. He told me:

Give Paul the spotlight. Make it all about him. When you’re out there, let him be the one up on stage. Meanwhile, you should be in the background telling everyone, “isn’t he great?” Keep pushing him and promoting him from behind the scenes until one day you aren’t back stage and everyone simply knows he’s in charge now.

There’s a lot of pride and ego you have to swallow to do this, but in order to avoid casting a tall shadow on them, you need to let them shine while you’re still around.  It creates an intermediate step where you and your sucessor are together, rather than an instant switch from you to them that would be jarring.

7) Get out of the way.

Of all the steps, this is by far the hardest. You’re handing off your baby you watched grow and develop and now you have to trust someone else to continue caring for it. If you don’t get out of the way, you’ll end up meddling in their work, preventing them from succeeding.

To truly be a successor, they have to be able to put their stamp on it. This only comes with the independence of full control. As Michael Skok told me:

It doesn’t matter if they succeed or fail; either way if you do it right, they’ll be to blame for it, not you.

In some ways it feels heartless; when you’re handing it off, you want to feel like you have some lasting value you can provide. However,  the best thing you can do is tell them you’re there if they need you, but otherwise absent.

I’m still working at this last step. Since I stayed on as CFO at Greenhorn Connect, I still have some duties with the business. These duties are a blessing and a curse; I still get to see how GHC is doing, but it also then tempts me to interject in Paul’s work to make observations and suggestions.

Luckily, Paul is very gracious about them and he’s also strong enough to stick to his guns and do what he thinks is best. I think I’m getting better at this last step of late, but I still catch myself at times trying to prevent Paul from making his own mistakes. I have to let him make his own mistakes or he won’t learn.

Succession is hard.  But to ensure good things continue beyond the lifespan of its creator, it’s an important step in the lifecycle of every organization. I hope these tips will help you keep your great organization living on.

What advice do you have for succession planning?