We do a lot of talking these days about becoming
an entrepreneur, following your passion, and
doing great things. Well, that’s easier said than
done. There are practical aspects of that equation
that can be enormously challenging to overcome.
For one thing, most of us are gainfully employed.
It isn’t easy to just pick up and leave a career
we’ve invested in, whether it’s the right move or
not. Then there’s the risk factor. We have
responsibilities, a mortgage to pay, kids to raise
and put through college. It’s hard to risk a sure
thing for an unknown, especially later in life.
Nevertheless, there’s a lot to be said for following
your dream. You may not get rich, but you will
enrich your life. And at least one school of
thought says that you’ll be more successful doing
what you love doing than anything else. I
couldn’t agree more.
I took a hard left turn 23 years into my career
and, although it’s been quite a challenge, it’s also
been incredibly satisfying and invigorating.
There’s nothing like jumping headfirst off a high
cliff to get the adrenaline flowing and make you
feel young again. But before you jump, do these
five things; they will help you make the right call.
1. Take a long, hard look in the mirror.
What do you see? If it’s someone who took the
path of least resistance early in life and has been
locked on to that trajectory ever since, who would
suffer deep regrets if she didn’t at least try to find
her true path, that’s some pretty good
motivation, right there.
If, on the other hand, you see someone with a
romantic notion of doing his own thing instead of
working for the Man, that’s probably not going to
work out so well. You’ve really got to figure out
what your motivation is. What are your objectives,
your priorities? What are you trying to prove and
to whom?
Understanding what your true motives and goals
are will help you and your family–an important
part of the equation, by the way–to assess the
risk and make the right decision. It’ll also help
you avoid waking up down the road and realizing
you made a change for all the wrong reasons, like
“the grass is always greener.”

2.Don’t try to be what you’re not.
You’re not really trying to change as much as
you’re trying to find the real you, the path you
were meant for. I know that sounds amorphous,
but that’s just the way it is. You’ll know it when
you find it. If you’re not sure, then keep looking.
I started out as an engineer, but that really
wasn’t for me. So I got into sales, then marketing.
Lo and behold, that was the real me. Everything
got easy. And I climbed the corporate ladder like
a monkey.

You see, people can change under very specific
conditions, but if changing your DNA, so to speak,
is a prerequisite for your career shift, I wouldn’t
do it unless you’ve got a considerable financial
safety net.

3. Look for problems, not solutions.
Most entrepreneurs are people looking to do
something new and different; they search for
ideas, for solutions. That’s usually the wrong
place to start. What you need to find first is a
problem that you feel passionate about solving.
With any luck, it’s one that you’re uniquely
qualified to solve.
One of the most important questions venture
capitalists ask when evaluating an enterprise is:
Does it solve a big problem? Does it eliminate a
customer pain point? Does it help customers
either do something they really want to do but
never could, or do something far better, easier, or
less expensively than ever before?
Another way to think of it: Don’t try to do
something great. Not initially. Just try to find a
problem you think needs to be solved and do
that. Mark Zuckerberg wasn’t trying to create a
company or do something big when he started
Facebook. He just thought it would be cool to be
able to rate women’s looks online. That was it.

4. Go where the money is.
I don’t care what anyone says: tossing out years
of experience in one career to jump to a new one,
perhaps even an entrepreneurial endeavor, is
extremely risky. Best case, you will take a
financial hit. And you have to be prepared for
various not-so-best-case scenarios, as well,
especially if you’ve got a family to support.
I’m not saying don’t do it, but consider this.
Giving up a solid paycheck to start something
new on a shoestring budget in a commodity
business where you might end up slugging it out
with entrenched competitors for single-digit profit
margins is for the birds.
Of course, money shouldn’t be your primary
motivation, but you shouldn’t throw caution to
the wind, either. Look at fields and industries that
have more than a snowball’s chance in hell of you
making it and making ends meet. Go for growth
markets in which venture capital firms are
investing, for example.

5.Find a great team.
There is tremendous power in groups–at least the right groups. The same goes for complementary
partnerships. Find a wingman, or be somebody
else’s wingman. Find a great team to be a part of or create one. Most successful start-ups have
more than one founder. Bill Gates had Paul Allen.
Google’s Larry Page had Sergey Brin. It’s true in
any field. It took four extraordinary people who
seemed anything but extraordinary at the time to make the Beatles.
Warren Bennis co-wrote an amazing book about
great groups called Organizing Genius: The
Secrets of Creative Collaboration. Even if your group isn’t magical, at
least you will have others to share the work and
the misery with. Remember: When you’re doing
something new or making a change, support is
key. No kidding.