Free Agent Part Two: On Big Decisions & Very Real Fears

THANK YOU for the outpouring of love and support last week. You helped me see without a doubt that I am making the right decision and that I won’t be alone on the road ahead.

I am so incredibly blessed to have such a supportive community. Each of you continue to blow me away with your kindness, intelligence and support!

A quick note on the survey:

So far almost 200 of you (!!!) have filled it out. Thank you! I’ll wrap-up the results in an upcoming post, but it’s not too late to share your thoughts!

I heard from a small handful of you that the posts have gotten too personal and “meta” and that you’d like to see more practical tips. Those will return soon, I promise! Between the book launch and quitting Google, life has taken center-stage, and it’s important to me that I let all of you in to “backstage” experience. However, I NEVER intend for this blog to be all about ME ME ME, so know that I am fully committed (now more than ever) to delivering the best possible content for all of you.

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A little backstory on the month leading up to my Big Decision

At SXSW in March, I was walking down Sixth Street with Andy Drish at 2am eating Philly Cheesesteaks, and he asked if I was going back to Google after my sabbatical. I hesitatingly said yes. He looked me in the eyes and said, “JB — you’re better than that.” I started crying…telling him I was too overwhelmed with my book launch to even THINK about leaving…and to be honest, I was too afraid to even entertain the thought. Looking back, I’m so thankful Andy had the guts to plant that very important seed, even though my response wasn’t a very receptive one at the time.

Fast-forward to May 15. I was chatting with my (now) very good friend Michael Ellsberg, author of a soon-to-be-released game-changing book called The Education of Millionaires, and he asked me, “How will you feel if one year from now you haven’t made any changes to your life?” My eyes welled up with tears (common theme, I know).

I could not imagine one year out, still in limbo, still hesitating. When I told Michael my fears of leaving Google and becoming self-employed, he looked at me and said, “You can do this. I — we (your network) — WILL NOT LET YOU FAIL.”

At that point, I had only known him for one week. And yet, Michael’s conviction, his genuine belief in me, and his encouragement felt like oxygen to my semi-suffocated, paralysis-by-analysis dream. It was on that day that I *knew* what I needed to do — I just needed to find the courage (and the financial footing) to do it. The decision-making roller-coaster continued as I spent the next month working through it all.

How I got my heart, gut, brain (and bank account) to play nice

Last week’s post focused mainly on the “what” and the “why” of my big decision — today I’m going to (do my best) to explain HOW I reached my decision — particularly after the conversations with Michael and Andy where I felt the need to reconcile my practical reality with my “I’m so inspired!” reality.

Bottom line: very deep down, my gut knew all along. But being the THINKER that I am, I had some work to do to rally the committee in my brain (particularly my hard-driving “show me the numbers so you don’t end up in a van by the river” CFO) so that I could actually muster the courage to leave my cushy job and go out on my own.

• Identify who is on the committee in your brain – this might be too woo woo for you, but many of us have a committee of voices contributing to any big decision (this is also often referred to as Parts Psychology). In my case, the big discussion was between my Creative Director (the one concerned with me doing my best work) and my CFO (the one concerned with making financially sound decisions). Neither voice is right or wrong – they represent various concerns we have about different aspects of a decision. In the end, you — the CEO — has the final say, but you might feel better to ask each of your “committee members” what they need in order to feel comfortable moving forward. To appease my CFO, I set an income goal for the month of June as a challenge to prove that I could do this without going broke. I’m happy to report that I reached my goal, but one week after I gave my two-weeks notice.

• How far will your savings stretch? You don’t have to have a saving account to make a big career decision (especially if you line up the next thing before you leave), but it certainly does help. It’s a fine line between saying, “If I wasn’t working full time, I could…” and meaning it, versus just using that as an excuse. In my case I did everything I could to maintain my sanity, my side hustle and my full-time job to avoid that “if/then” limiting belief. Once both became too much to handle, I looked to my savings account to provide my runway. I have about six months of savings, and I was finally willing to spend every single dime to take the risk of making it on my own. I took solace in knowing that even if I didn’t lift a finger I could live for six months; so I felt a lot better once I realized how hard I was willing to work in that time, and that I could definitely find creative ways to make money.

• Rank “Worst Case Scenario” action steps – Let’s say you take a great leap, and you fail. What then? I worked through the worst case scenario, particularly on the financial side. I made a list of back-up plans and ranked them. If I am not succeeding on my own (ie making enough to pay my bills) within six months, I will do the following (in order): use my cash savings, sell my car, sell my stocks, GET A JOB, then sell my condo. You can see that I would look for employment again before it came to selling (or defaulting on) my house. What does your worst case scenario look like, and what would a course of action look like?

• Expect the unexpected. Accept that you will hit a dip. Accept that you are choosing a certain level of chaos and uncertainty. These were all HUGE for me. If you can’t already tell, I’m a planner (haha, hello Captain Obvious) — I like to have things mapped out, and for a while that really worked for me. Before I started college, I mapped out every single class I needed to take in a fancy four-year spreadsheet. Jumping into self-employment means ACCEPTING chaos and accepting uncertainty. I also KNOW that I will hit many dips where I feel like a failure and want to quit, or maybe even regret my decision. But I know that I will work through them, and that they are par for the course when taking great leaps.

• Realize that you can’t plan everything before making the decision. When it comes to big decisions, you will not always have all of the information you need. Sometimes you have to take the first two steps so that you can see the next two. While I did some income modeling, I do not have an accurate view of exactly how I will consistently make money for the next 12 months (though I have many ideas), and that is slightly terrifying. But this is what I signed up for, and it’s the challenge that I asked for to continue learning and growing in my life. I knew that at some point I needed to leap in order to give myself the real motivation to figure it out. I also specifically chose not to look for contract work with someone else as a safety net — I would have just stayed with Google part-time if that’s what I wanted; instead, I had to really challenge myself to devote my FULL time and attention to my own business, not someone else’s out of fear that I wouldn’t be successful on my own.

• Avoid fear-based decisions. This one is a biggie. Imagine sticking your arms out like an airplane — on your left fingertips is fear-based decision-making, and on your right is “soul-stirring,” intuition and excitement-based decision-making. Where do you tend to fall on this spectrum? Choose one of your proudest decisions — was it based fear or avoidance of pain, or was it about moving toward something thrilling? This requires discipline, but try to catch yourself when you are making choices based on fear, and instead ask, “What do I want to run toward?”

• Engage your network. Your network is much bigger than you even realize. There are many people in this world who will send you love and support — even if it comes from unexpected places. Especially from unexpected places! It’s amazing to me that someone like Michael could play such a transformative role in my life after only a week of knowing him, but it proved the true power of connecting with individuals who see the best in you and the kindness of “strangers” who are willing to offer their guidance and support. Don’t feel like you have to make a decision (or face the consequences of a choice) in isolation — remember that there are many people who have gone before you, and many who will be there to catch you if you fall.

• Ask the big questions. What will you regret more? What choice honors your biggest dreams? If not now, when? What are you waiting for? What if you are MORE successful than you can even imagine? What would people you most respect advise you to do? In my case, all answers pointed to taking the leap. Particularly because I’m in the personal development field, I felt it was critically important to walk my own talk — otherwise I’d feel like a fraud.

Despite working through everything above, I am still facing some very real fears. Right now they tend cross my brain like clouds passing — I watch the dark ones carefully and try to address the practical side of the concerns without giving them too much attention (for fear that focusing on them will cause them to create a torrential downpour of despair).

My remaining Very Real Fears:

• Do I deserve all this freedom? Is the other shoe going to drop?
• How do I balance working hard versus getting rest, knowing that I want more than anything to make this work?
• What if I get bored or burned-out doing my own work?
• What if something terrible happens and I am unable to work?
• What if I have some crazy medical emergency that sends me spiraling into mountains of debt (even with health coverage)?
• Will I still be able to save money for emergencies and retirement?
• Will I be able to get back into a routine that works? Will I learn to say no more so that I don’t keep getting overwhelmed?
• Will I be able to prioritize and balance “revenue-generating” activities with everything else?

You can see that most of these are hypotheticals or things that I will figure out as I go — so I just remind myself to “cross that bridge when I get there,” confident that I will be able to figure it out.

As for the “What if I end up living in a van down by the river” concern? I smile every time I think of Marc Luber’s encouraging words: “If you actually do end up in a van down by the river, you’re someone who will for sure find a way to teach swimming lessons, start a fishing business or give kayak tours.” And that goes for you too, I’m sure

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The Greatest “Out in the Wild” LAC Book Picture Yet!

This picture is just too great for words!!! Katie (of KatieBlogs.com) takes Hootie on the road…and gives him some reading material so he doesn’t get bored:

CLASSIC. Katie's Hooters Owl wises up on Life After College.