Resume skimmers seem to be looking for brands, big names of companies. They want to know “who you worked for,” and it better be someplace impressive, or into the reject pile you go. Truth is: “self employed” might have a bad rap in the hiring world. But yet, a former business owner could turn out to be the hardest worker you ever had.
Why do self employed people seem to be the Rodney Dangerfields of the 2025 job market?
You may have noticed: there’s no spot to shout out, “I RAN MY OWN BUSINESS” on the application form. A copywriter friend of mine says ATS (applicant tracking software) is at least partially to blame for this “scan and toss” scenario that doesn’t feel so good when you’re the applicant. Self-employed job seekers, shake off the rejection, before you start feeling like 20 years of real-world experience just got thrown into the job search trash bin.
WHAT COMPANY DID YOU WORK FOR? Sometimes you’ll even get a form to fill out on the job application where you aren’t able to type in the name of a company. Instead, you’re prompted to select from an existing list of companies that has been supplied to you in the dropdown.
What is that about? Just another example of the tragic, deeply concerning, society-impacting disconnect between computer and human that’s causing a massive rift between hiring companies and the talented workers who rightfully belong on their team, but probably won’t make it past the form-filling-out phase.
You forgot to include “self employed,” or a spot to type my company name, on your job application.
Who designed this job application form, and why would you exclude my self-employed experience, or my work for a very small startup, as a viable path toward gainful employment in 2025?
What about me personally… the copywriter behind this post? Do I have an employment gap on my resume? Well… it might look that way, because there’s no Big Name Company listed as my employer since 2003. But I, and many other online business owners and entrepreneurs, have worked our behinds off for ALL this time and developed mad skills in the trenches.
I would NEVER be able to claim so much experience across so many industries, if I hadn’t freelanced in my own business.
YES, self-employed counts. In fact, a business owner possesses quite a unique and powerful skillset, if I do say so myself.
And ironically, the most likely candidate who would actually empathise with what bosses go through in their ongoing mission to inspire, motivate and coax productivity from their team, is the person who has run their own business.
Business owners, even ones who run micro businesses, might actually deliver exactly what your company needs.
Will that occur to hiring managers as they run their eyes over my resume, or yours if you did the online biz thing? Probably not. Because until a corporate boss has actually toiled in the self-employed role, they likely won’t relate to us even as our daily pressures and goals might be strikingly similar.
Someone needs to tell the corporate higher-ups and the hiring managers. I guess today it will be me.
If you want fresh blood fighting for your company, the right self-employed person could be the missing puzzle piece that sets you free.
It’s true. Bringing a former business owner on board could revolutionize the way you run your department. You just need to match the personality and the skillset with the need. That part’s really important.
DON’T overlook the potential for a former business owner to bring absolute MAGIC to your work life
Here’s what someone who’s run their own show will relate with that you, as a boss yourself, probably experience on a daily basis:
- Striving toward the financial goals (this is probably the hardest part about being your own boss, especially if you’re in a creative field and not necessarily high on “money sense”)
- Putting out fires on the daily (tons of QA issues; customers complaining… but how do you power through these problems?)
- Taking criticism (emotional intelligence may be achieved through experience, but it’s not something that can be taught)
- Managing personalities (the Slacker, the Helper, the Team Player, the Brown Noser, the Sneak, the Codependent, The Star Performer, the Rebel, the Martyr, the Gossip, the Complainer, the VIP, the Underachiever… the list goes on)
- Driving human productivity (How do you get people to do what you need them to do?)
- Dealing with complex people problems (You guys have human resources backing you for that. A small business owner has hope and prayers.)
Being the boss of a former business owner feels pretty sweet.
Here are some perks you’ll probably get from someone who’s run their own business that’s now working for you (meaning, now you’re their boss):
- Has boatloads of “boss empathy” (actual, real understanding of what you’re going through)
- Feels relieved to not carry the leadership burden on their own shoulders for once
- Recognizes the need for daily motivation
- Sees the long-term vision in the small details
- Offers unwavering support to bosses who lead with love (of course, there’s always the possibility of having to deal with a toxic boss too)
- Much more likely to appreciate and be on board with the team vibe
- May be prone to telling it like it is, if you can handle that (might be revolutionary, might be their downfall)
- Probably not interested in office drama and he-said, she-said
- Does not nickel and dime, or keep score, because we’re big picture thinkers now… we’ve been in your spot
- Strong problem solving, reasoning and executive function skills
- Far more likely to support you in their daily communication and actions
- Likely really good at self-management and working independently
- May be able to function as a mini-you, sub-in boss in your absence (think assistant manager to lighten the daily load)
A former business owner might just be your model employee, because… gratitude!
- Grateful not to have ALL the benefits on their shoulders (sure, the self employed can get health insurance… it’s just a lot to deal with and we’re glad to lean on the company for that)
- Your W2 form and tax withholding practices feel like a mental vacation for us (most probably don’t consider that small biz owers must keep track of profits and pay quarterly taxes to the IRS)
- Grateful for boundaries between personal time and work time (biz owners feel that endless pressure)
- Those days off where we can actually turn our brain from Always Worried About Work mode to Relax and Have Fun mode, feel like heaven to the formerly self-employed.
Extend respect to people who tried hard to win in business.
They’ve likely learned some tough lessons that make them a valuable asset to your team.
A person who’s run their own business… either ecommerce, brick-and-mortar, or remote service-based online… has his or her own special skills, talents and lessons mastered.
Maybe they didn’t break six figures. Maybe it was only a small supplement to the family income. Maybe they had to file bankruptcy. Who knows? But the outcome doesn’t matter so much as what this person learned while giving solo or small business a go.
A person who has given their all in business has undergone incredible personal growth that is sure to serve you well.
Skills a small business owner might have that could be useful:
- Accounting and bookkeeping skills
- Tax filing and health insurance procurement skills
- Social media marketing skills
- Public speaking skills
- Graphic design skills
- Email marketing skills
- Web design skills
- Specialized knowledge within a niche, like real estate, landscaping, culinary, online business, builder, crafter, other
And let’s not forget these professional strengths…
- Business communication
- Organizational ability
- Negotation skills
- Business planning and strategizing
- Time management
- Customer service
- Leadership and team building
- Team collaboration and support
- Telescoping vision – able to predict outcomes long before they happen
Any downside? Business owners may need to re-acclimate to the following facts of corporate life:
It’s true, self-employed peeps may be rusty or underdeveloped in some areas. Be on the lookout for a potential catch-up struggle in these areas; support, inform, remind, or redirect as needed:
- Strictly enforced policies and procedures
- Chain of command in leadership
- Communication – spoken and unspoken rules
- Adapting to a set work schedule if theirs was super flexible as a business owner
- Being mindful of personnel issues and professional conduct expectations
- Having your time strictly controlled, as applicable
Giving that self-employed person a fair shot
No, not everyone who had a business will be the right fit for your organization. But let’s not treat the “self employed business owner” status like a scarlet letter of shame. And let’s stop downplaying the potential for a really strong team member to come out of this experience.
Instead of hiding your self-employment, wear the title like a badge, because that’s what it is.
I RAN MY OWN BUSINESS. I MADE MY OWN LIVING. Only some get to enjoy the honor and privilege of saying that. Nobody told you what a hard worker you were, nobody congratulated you for all the things you learned, doing it all on your own. Allow me to congratulate you now.
So: If you ran your own biz, as a “self employed person,” will you talk that up and shout out your worthiness, the way you should, to your future employer?
And if you’re the hiring manager: will you give that self employed person a chance?
20-year copywriter Dina Gio hails from a copywriting background that includes both formal training and real-world experience. She spent 7 years writing marketing collateral on a full-time basis for a well-known, Fortune 500 company. She has run her own online businesses, serving writing clients and selling content with private label rights, since the year 2003. If you spot her “self employed” status on a resume, or anybody’s for that matter, don’t downplay the magnitude of this. You might just end up with a rare gem of an employee in your corner.
If you freelance and/or would love job searching tips, sign up for Dina’s List.
If you’re in search of a copywriter or content manager to support your team, email dinagio@dinagio.com.