How to Sell Yourself as an Employee After Being an Entrepreneur

Let’s face it—running a business is hard work. And if you decide that your business has run its course, you’ve successfully exited, or you’re just tired of the daily grind, it can be difficult to move on. Plus, the idea of “getting back into the job market” can be even more daunting.

Aside from where to start (a feeling we all have at one point or another when job searching), some of the common issues my clients encounter during this transition involve finding the right role (and subsequently, their fit in the job market), writing a resume and cover letter, and effectively interviewing and talking about their experience.

If you’re in the process of moving from entrepreneur to employee, here’s what you should be focused on in your job search.

Finding the Right Role

For many, finding the right role and fit is the most difficult part of the process. I’ve had clients who have run businesses for decades and come into the workforce feeling like they’re out of place. As an entrepreneur, this is expected—you’re used to wearing multiple hats and getting fairly decent at plenty of roles, yet rarely have the opportunity to work toward being an expert at any one position.

To find your identity in the workforce, there are a number of methods you can employ (pardon the awful pun). For example, with a previous client who ran a residential real-estate organization, we talked a lot in our initial session about the aspect of his work he loved most: solving problems. We brainstormed what those problems actually looked like, discussed what sort of impact or influence they wanted to have on solving those problems, and sought out both organizations and roles that incorporated and offered this capacity.

With another client, we conducted an inventory of all their skills and accomplishments and grouped them into different job areas. From there, we had multiple “skills buckets” that we investigated further through informational interviews to get a sense of what careers they gravitated toward.

If you’re still struggling to come up with ideas, you can always take a career quiz or personality test. (That said, I recommend taking these tests with a grain of salt, as they’re often not personalized to you, but rather spitting out a few answers based on a simple algorithm.) Or, you can check out one of these free resources or fill out this worksheet to help find your passion.

Regardless of which route you take, it’s best to verify all your hard research on the roles you’ve landed on by meeting with people working in those fields to help figure out if it’s the right option for you (these email templates can help in reaching out to people for informational interviews).

Writing Your Resume and Cover Letter

You’re set on a role that you’re interested in and now you need to start surveying your transferable skills and building out your value proposition. (If you’re not familiar with what a value proposition involves, it’s essentially about defining and effectively communicating what makes you stand out from the competition—or, what you can offer better than any other applicant.)

The primary purpose of a resume or cover letter is to get you in front of an interviewer. So, remember that there are some things you’ve accomplished that are going to be more marketable for the roles you’re seeking and others that aren’t as relevant that you may have to leave out.

It helps to look at the “roles and responsibilities” section of the job description. Get a feel for what these jobs are seeking—both for direct and indirectly related skills—and use that as a barometer for evaluating your own skills that you want to present. Don’t worry if you’ve only had one role on your resume, or if it’s been a significant amount of time since you’ve been an employee. Present your experience in a concise and digestible way for the hiring team to see what strengths you bring.

In the case of applying for a digital marketing specialist role, here’s an example of what your entrepreneurial experience could look like on a resume.

Owner/Digital Media Strategist, Wright Digital 

Vancouver, British Columbia, June 2011 - December 2018

• Built, managed, and grew Wright Digital’s social media presence across multiple channels (Instagram, Facebook page and group, Pinterest, and Twitter), led to an overall increase in monthly web traffic by 34% since October 2018.
• Created Yelp business page that now includes nearly 1,500 user views—up 27% since May 2018; generated over 115 customer leads with a 14% purchase conversion rate.
• Utilized Google Analytics and Facebook Pixel to better understand our ideal audience, retarget website traffic visitors, and create more effective advertisements based on our ideal user personas.

In your cover letter, you want to effectively explain the catalyst for making the switch from business owner to this specific job or career. Focus more on what’s drawing you toward your new path rather than on what might have driven you away from being an entrepreneur.

For example, if you were applying for a role as a junior UX designer at an e-commerce site, your first few lines in a cover letter might look something like this:

When I was an entrepreneur, to ensure the success of my business, I had to learn and take on many responsibilities—marketing, sales, accounting, recruitment, and so many more.

What I loved most about my role—and where my true passion lies—is in helping small businesses solve user experience dilemmas so they can do what they do best. What I’m really seeking is an opportunity where I can devote my time to solely understanding customers and their online shopping habits on a deeper level, and leverage that in-depth knowledge to create a flawless user experience for those looking to purchase outdoor and recreational gear for their upcoming summer camping adventures.

You’ll then want to build your cover letter body by addressing how you bring relevant skills from your past experience as an entrepreneur. Cover letters are an excellent tool to differentiate yourself in the job market, especially when you’re coming from an unconventional background—so be sure to actually write one, first of all, and spend an extra bit of time making yours stand out.

(This article on skills-based resumes and this one on the perfect cover letter to show off your skills might help.)

Answering Interview Questions

The first step is familiarizing yourself with the interview process for your industry. There will be standard parts consistent across most industries (like these common interview questions), however, more technical roles will have other components, such as answering technical interview questions or brain teasers, while others may require putting together a presentation or writing assessment.

One of my recent clients was coming off a 12-year stint running their own business. They had recruited, interviewed, and hired individuals before, but had little experience being on the other end of the process. They came to me after struggling through their first few interviews and needed help on where to improve. I took them through an interview prep session and conducted a mock interview to assess their skill level, and determined that their biggest barriers were their ability to nail their introductory pitch and brainstorm proper examples to address the behavioral questions (specifically ones revolving around working with colleagues) that they kept encountering.

The key thing to remember is that you always want to find a way to relate your answers to the industry and role that you’re applying for. If you’re asked a question about a time that you disagreed with a supervisor, yet you’ve technically never had a supervisor, it’s best to acknowledge the gap and walk them through what you would do in that scenario instead.

For example:

“Thank you for your question. In my experience as an entrepreneur, I’ve frequently been the person who has ‘approved’ all business decisions. However, what I found my employees doing that I responded best to in these situations, and what I would do when faced with this dilemma, is to first put myself in their shoes and ask myself if there’s potentially any information that I’m not privy to that would yield such a decision.

If I still found myself disagreeing with the decision, I would come prepared with a logical presentation and sound reasoning why I felt an alternative direction would be more effective. I’d communicate this with an open mind for what I might uncover and come without any expectations of my supervisor reversing their decision.

It isn’t about being right necessarily, it’s about gaining greater context into the decision-making process, expressing my opinion in the right environment, and reminding myself that there is often a disconnect between what employees see on the day-to-day and what supervisors are dealing with for the bigger picture.”

Reentering the job market after being an entrepreneur is a big career move, and it’s important to acknowledge that throughout the process. Give yourself credit for making the switch, take pride in the small wins, and watch them build toward your overall goal of landing the right role.