2016, Alexander Technology Group, entrepreneur, Jason Alexander, talent, talent development, tech, tech talent

An Entrepreneur’s Journey Back to the Workforce

By: Jason Alexander, Managing Partner,
Alexander Technology Group

If you’ve been out on your
own as an entrepreneur, the return to the mainstream workplace can be a
daunting journey. How will you re-acclimate to regular accountability?
What direction will best suit you on this new or revisited path? Why are
you returning and is it for the right reasons? These questions can
naturally build up and, combined with the strong possibility of focusing on the
wrong priorities, it could make any mortal’s head explode. 
Whether your reasoning is
derived from a necessary change of pace, the realization of a new dream, or the
simple reality that entrepreneurship just didn’t serve you the way you had
hoped, you are preparing to journey down a thoroughly blazed trail that many
strong, noble, and honorable professionals have traveled. More concisely
put, you ain’t alone.
First things first…
Let’s just immediately
dispel the stress and pressure you may be unjustifiably bringing upon yourself
for not being tough enough or not sticking with your dream. Don’t forget that
you’ve already done what 99% of your peers didn’t have the guts to do. You
Having spent time as a
failed and successful entrepreneur, I can say from experience that
entrepreneurship is one of the greatest experiences in the world for defining
one’s true self. Outside of the esoteric, Zen-like meaning of such a
ritual, I’m simply referring to defining the stuff you truly like and the stuff
you truly don’t.
There are many things that
I can successfully accomplish due to adequate toughness but I just might not
feel like it. There are other challenges I may choose to take on that may
or may not end in triumph. Only time will tell. My point here is to
distract you from unnecessary self-doubt and draw your attention to the pride
you should feel because you stepped up to the plate, took a swing and, well,
some other sporting analogy that spells out “give yourself a break – life is
Now onto the second thing…
Now that we’ve successfully
meditated our way to a lucid mindset and a slow pace of breathing, let’s think
about what happens when the rubber meets the road. What are you going to
do? What do you want to do? Here’s a simple drill that might get your
mind churning in the right direction.
Step 1: Don’t go on any job
boards/websites yet. All this will do is get you thinking about how you can
retrofit yourself, reactively, into an existing role rather than thinking about
shaping the kind of role within the type of organization that you
desire. Remember the reasons you became an entrepreneur in the first place?
I can’t imagine the deep-seated desire to control your own destiny wasn’t part
of the equation—and we’re not giving up on that part of the dream unless we
absolutely must.
Step 2: Write down a simple
list of the things you know you do well. By this, I don’t mean
“organizational skills” or “working with people” but the measurable, tangible
results you factually know you deliver better than your peers. 
Step 3: Cross off the items
that you have no desire to do. 
Step 4: Putting your
entrepreneurial mind to work, think of the organizational types, verticals,
and/or inflection points where these remaining attributes would be most
valuable. Now you’ve defined the profile of the organization you should be
seeking employment within.
Knowing what matters…
The most common mistake I
see with entrepreneurs reentering the workforce is the propensity to forget
everything they learned as an employer while delivering their value proposition. Remember
that your entrepreneurial endeavors have earned you a homeschooled black belt
in pragmatism or, better put, gravitating to the realistic versus the
Self-doubt and inadequacy, feelings
at least mildly present in 99.9% of those seeking employment, tend to drive us
to presenting through theoretical means. Instead, make it a point to flex
the muscles you’ve spent all this time building by cutting through any
superficial theory and talking frankly about problems you have solved, deals
you have won, and your absolutely clear vision on what’s next. 
There’s always tomorrow…
As long as you are walking
away from a previous entrepreneurial goal for a solid, qualified reason and not
because you had a bad week, remember that you learned a lot and that life is
all about new experiences. Reentering the workforce could prove to be more
professionally satisfying, more lucrative, may allow for more precious time
with family, or perhaps open your mind to your next entrepreneurial
vision. Regardless, while we do live in the real world and have to ensure
we’re getting paid/paying bills, make sure to spend at least a little time
following the fun. It’s all going to work out in the end.

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