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Job Search Tips for Former Business Owners

Job Search

Are you re-launching your job search after being an entrepreneur? You’re not alone. By September 2020, nearly 100,000 small businesses permanently closed their doors due to COVID-19 hardships. We know that little fact doesn’t make it any easier. But your job search doesn’t need to be a struggle as well. Your transition from self-employment to working for someone else can be a positive one. It’s all in your attitude, how you present yourself, what you’re willing to let go (so that your other skills can shine), and the network and resources you have in your corner.

Find Acceptance

“You’ve lost something you worked hard for, and even though you weren’t to blame, it’s still painful,” says Alison Doyle, a job search expert for The Balance Careers. She adds that refusing to be paralyzed by the past will help you focus on what you can control, including what excites you and what you’d like to do in the future. 

Losing a business can be like losing a loved one or mourning the end of a relationship—you need to give yourself permission to follow the usual stages of grief: denial, anger, bargaining/rationalization, depression/despair and, finally, acceptance. You may even want to consult a mental health professional to help you.

The Strategic CFO outlines these stages from an entrepreneurial perspective here. Entering the job search while you’re still raw with anger, hurt, sadness, or confusion about the loss won’t take you far. Instead, find a way to get excited about your new chapter. Remind yourself that it’s time to focus on your talent and skills while giving up the pitfalls of business ownership.

To do this, you may need to adjust how you treat yourself, says Alice Boyes, PhD, a former clinical psychologist and author of The Healthy Mind Toolkit.

“Self-compassion improves people’s participation in groups and is associated with a more adaptive attitude to failure. People who are self-compassionate recover better from psychological knocks, like relationship breakups and career setbacks,” Boyes says. She recommends learning compassionate self-talk to get yourself back into loving yourself and your career before putting yourself out there as a job candidate.

Sell Your Specific Skills

It may sound like a silly question to answer at this stage in your career, but do you even know what you want to do? As a recovering entrepreneur, you have two main choices: go back to the line-of-business skills and the position you were in before business ownership, or “level up” using the executive skills you picked up as a business owner, either in your original field or a new one.

For instance, if you went into business for yourself as a network engineer, you could go back to that position, you could go after director of IT or CTO-type positions if you gained executive skills in that same area. On the other hand, you could consider management or executive positions in operations, sales, customer success, etc., if you learned over the years of running a business that one of those areas is a sweet spot (and you have the measurable results to prove it).

You may need to work extra hard to match your skills with each job that interests you. Generally touting that you wore the many hats of a business owner won’t cut it. Try these exercises:

  • Take a career aptitude test if you’re entirely unsure where to start with your job search.
  • Tailor your resume to each job for which you’re applying. There is no one-size-fits-all resume.
  • Focus on specific, measurable accomplishments when listing work history.
  • Practice answering interview questions using the STAR method, particularly the dreaded “tell me about a time you failed,” which can make-or-break your “this is what business ownership taught me” moment.

Show You’re a Team Player

The biggest concern about hiring some who was self-employed is the genuine possibility you’ll have trouble collaborating and “staying in your lane.” You need to prove you’re OK not being the boss if that’s not what the job requires you to be.

“I recently spoke with a senior finance professional who was facing this exact scenario,” says Dave Benjamin, Executive Search Practice Director at The HT Group. “The first thing we addressed was the idea of being collaborative but also knowing when to concede ‘ownership’ in areas they were used to managing on their own. This involves having trust in the individuals around them to carry out their specific tasks but getting a clear picture on the front end of their fit within the team/organization.”

Focus on the positive traits business ownership gave you instead. Monster lays out a few here, including:

  • You’re both a strategic thinker and a doer.
  • You know how to delegate and collaborate to meet objectives.
  • You can influence and motivate the people around you.
  • You’re both mentor-minded and a constant learner.

Consider Easing Back In

About 1,640 CEOs left their jobs in 2019. That’s a jump of 13% from 2018 and the highest turnover rate since 2002. The surge continued into 2020, with January’s total reaching nearly 40% more than January 2019. The pandemic slowed turnover temporarily, but plenty of Baby Boomers are still expected to retire in the coming months. Many of these departures are leaving critical gaps in leadership. For example, nearly half of U.S. CFOs haven’t named successors to fill their shoes when they leave, and they aren’t unique among the C-suite.

What does this have to do with you?

“It’s critical to get out there and let your vendors, customers, and C-level peers know that you’re looking for a position,” says Mark Turpin, The HT Group founder and CEO. “Many of these executive-level jobs aren’t advertised. The best way to find them is through your network and executive recruiters.”

Plus, organizations are reluctant to permanently fill these critical executive positions right now, due to so much uncertainty. For this reason, you may want to consider serving as an interim or fractional executive. As a former business owner, you may be a rare and valued find for these types of positions while you search for a permanent job. It’s a win-win for you and the organizations in need of your guidance.

“Starting in interim or fractional roles can help entrepreneurs ease back into a more structured setting and hone-in on specific skills that would add immediate value,” Benjamin explains. “The availability of full-time opportunities will depend on how long you’ve been out of a full-time scenario, so keeping both options open will increase your odds of landing a position.”

Fill out this form to contact The HT Group Executive Search team for professional- and executive-level opportunities and learn more about The HT Group’s Consulting Services, including interim and fractional executive opportunities here. Leaving business ownership behind is hard. But there are benefits to finding the right fit elsewhere, too. The perfect organization is looking for your skills and experience to help them move forward. They just need to find you.