Posted: 03/07/2015

It often requires risk to follow your heart, or pursue a higher calling. When I look back on risks that paid off for me, I notice they have something in common…

In every case, my odds of success would have dropped if I’d waited. Let me share examples, and then pose questions to help you determine if it’s time to start following your heart.

In 1999, I applied to the BMI Musical Theater Workshop in NYC. There were roughly 500 submissions, and 45 people were accepted. When I learned I was among them, I gave up my rent-controlled apartment in Berkeley, CA and uprooted myself to NYC.

During my third and fourth years in the workshop, I had the chance to be mentored by Maury Yeston, who wrote the musicals “Nine”, “Titanic”, and “Grand Hotel”.

However, he stepped down from the workshop in 2003. So if I’d waited a few years, I would’ve lost the chance to learn from Maury.

Moreover, if I’d waited, I might not have been accepted at all. In recent years, the annual submission count has climbed to 2,000+ (whoa!), raising the bar and making it harder than ever to get in.

After moving to NYC, I went hunting for a condo in Brooklyn. I was warned that home prices had been rising for four years straight. Some people worried I was buying at the “top of the market”. However, 16 years later, I sold that condo for five times what I paid!

If I’d waited, my down payment dollars would’ve deflated in value, relative to the cost of housing. It would also have become impossible for me to get a loan, since home financing dried up after the subprime mortgage crisis (2007-2009) and I am self-employed.

From 2001 to 2009, I built an email list of 23,000+ vegans. How?

I was an early adapter of Internet marketing strategies, before they become common. Back in 2001, there were fewer vegan websites competing for rank in search engines like Google. And fewer websites with compelling opt-in offers.

I created a compelling optin offer at And unlike today, I could buy clicks for a penny each (through pay per click advertising).

Had I waited, I would have lost all these advantages!

In 2010, my California home was “underwater” and I could no longer justify making the loan payments. Hoping to negotiate better terms with my lenders, I put my lifetime of good credit at risk and defaulted on my loans.

After a year, my second lender Citi Mortgage caved in; they settled my loan for 10% of the balance. But they only did so because my first lender would’ve received all of the sales proceeds in a foreclosure.

Had I waited until housing values rebounded, Citi could’ve recouped its loan by foreclosing, and would never have considered settling for 10% of the balance!

There are also industry-wide trends demonstrating the importance of timing.

Around 1990, it was much easier for songwriters to get staff writing jobs in Nashville – and get their songs recorded. Today, due to illegal downloads, the extinction of albums, and more artists writing their own songs, there are far fewer opportunities for songwriters to get their songs recorded.

And during the “dot com bubble” (1997–2000), it was easy for online companies to raise investor capital, even those that hadn’t yet earned a penny of profit. In the years following, raising money became much harder.

So I pose the question:

If you wait, will following your heart get easier or harder?

If you’re single now – or married with no children – will you still have the freedom to take bold risks once you have a family?

If you put it off following your heart, will you still have the same health and vitality? Will the economy be as good? Will the startup costs be higher? Will the people who could’ve helped and mentored you still be available?

You may not know all the answers. But unless you KNOW things will get easier in the future, why wait?

Even if you fail, there’s a big advantage to failing earlier in life. Whether you’re 35 or 55 today, starting now – versus later – will give you more time to recover, learn from your mistakes, and benefit from what you learned.

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