An Entrepreneur’s Journey Back to the Workforce

Feb 16, 2021

Posted by: Jason Alexander, Managing Partner, BANKW Staffing

Kbwfinancial team jason alexanderIf 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 percent of your peers didn’t have the guts to do. You tried.

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 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 short.”

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 your entrepreneurial endeavors have earned you a home-schooled black belt in pragmatism or, better put, gravitating to the realistic versus the theoretical.

Self-doubt and inadequacy, feelings at least mildly present in 99.9 percent 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.

About BANKW Staffing

Through its portfolio companies, KBW Financial Staffing & Recruiting, Alexander Technology Group, The Nagler Group, Sales Search Partners, and KNF&T Staffing Resources, BANKW Staffing, LLC is the leading regional provider of temporary and direct-hire staffing services in the areas of finance, accounting, information technology, office and administration, legal, human resources, and sales.

BANKW Staffing companies have received over 100 awards for rapid growth, business excellence, and workplace quality. Recognition includes Inc. 500, Boston Business Journal’s “Best Places to Work” and Business NH Magazine’s “Business of the Year”.

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