Battle-Tested: Selling Self-Employment on a Resume

We have been living in a renaissance of entrepreneurial thinking and ambition for the last 20 years. The rapid rise of the internet, increase in the overall education level of the population, and ease of access to business-level resources for the common man has opened a very particular door for tens of thousands of organized, talented individuals: self-employment.

Some of these individuals decide to return to the working world, and when they do, they would like to think what they learned and experienced when running their own company makes them a more valuable and more capable prospect for employment. Some employers value the courage and dedication it takes to run your own small business. Others see it as a useless gap in your work history.

Nevertheless, entrepreneurs need a way to communicate their unique knowledge in the context of becoming an employee again, and that second first job search is not always an easy one. Listing self-employment on a resume can be a major asset if done correctly, or a red flag to potential employers if done wrong. If you were recently self-employed and you are looking to return to the working world, here are some things to consider in putting self-employment on a resume.

The Professional to Corporate Path

There has always been a large and lucrative market for management consulting, freelance work, and business-to-business independent professional services. Because the best in their fields are often able to find better self employment opportunities outside of the traditional salaried model, many of the most accomplished professionals not only prefer to work on their own, but thrive.

Bringing experiences like these back to the corporate workplace presents a prospective employer with a unique opportunity. What would it cost, for example, to provide senior management at even a moderately sized corporation with the opportunity to learn about so many other organizations so efficiently? Does one person’s salary even begin to compare to that level of value?

When composing a resume or persuading a hiring manager the value of your experience far exceeds the cost of employing you, it is best to present your skills in the context of synthesis. You’ve had a clear and ongoing opportunity to compare methodologies, institutional knowledge, and management philosophies across companies and industries at a level that is frankly out of the reach of even the most sophisticated corporate executive. Leaving aside whatever your new responsibilities and job title will be, you should point out just putting ten people at a time in a room with you and letting them ask you questions would be worth whatever salary you are seeking.

Part-Time Self-Employment

Any time you are running your own company, you are learning things no employee will ever know and you are doing it while are sharpening your professional and workplace skills to the point where they are worth paying for. Your paycheck depends on you alone, your project management, the work that you perform, so you learn how to hone your skills with a drive and urgency unparalleled by the average desk jockey.

Getting good enough at something so that you are attracting clients and customers is not an easy thing to do, especially when the rest of the world is a click away offering a lower price. There’s no payroll department dropping a check on your desk every two weeks when you are running the shop, and the prize for second place is losing the gig.

Self-employed man gets up for work in his home office, to run his own company as an entrepreneur and learn valuable skills and work experience
Every day is a battle for entrepreneurs, resume writing shouldn’t have to be.

Presenting this information to a hiring manager might seem like you are selling part time skill for a full time wage. The reality is the skills you put on your resume were fired and hammered in a crucible of necessity. It is the context that counts when it comes to actually making money instead of earning it. When an employee gets it wrong, the work gets sent back and they try again. When an entrepreneur gets it wrong, they miss meals. Clarify how seriously you take results, and your boss will get it, because that’s the world they live in. Make sure your new boss knows that what you are bringing to your new workplace is more than just employment history.

Unemployment to Self-Employment

If it were truly the case that all self-employed people were actually unemployed people, then every company in America was founded by someone who was out of work. Any hiring manager who is honest with themselves is going to admit they would much rather have a person who built their own job in the face of unemployment than a person who did not. Turning unemployment into opportunity is how winning is done, and the one thing all hiring managers must admit is in short supply in the modern workplace are wheels-on-the-road winners.

The only way to portray your entreprenurial instincts properly is to demonstrate you can turn any set of circumstances into an opportunity for achievement. Behold what I have accomplished with little. What might I accomplish with more? And who stands to benefit besides me?

If you get the right person’s attention with that pitch, you may find your path from unemployment to self-employment will lead you straight to the top.

Super Bowls, horse races and wars are won by inches. So are careers. Add that self employment to your resume, and show it as what it is- some of the best employment experience that anyone can have. There’s no guarantee you’ll be able to find a good job or even a better job, but the truth is if you are one of the scarce few who can build something out of nothing, you bring skills to a workplace that cannot be taught, bought or borrowed. They can only be learned the hard way, and it is the people who learn lessons the hard way that move mountains, and build companies.

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