Entrepreneurs: You do Know You’re Unemployable, Right?

Are you an entrepreneur, starting a business? Or a  single-shingle intellectual gunslinger-type expert working as business consultant, planner, coach, or something similar? Are you making it on your own?

If so, you do know you’re unemployable now, right?

I don’t want to be the bearer of bad news, but I think you should know. I’m not saying it’s a big deal, or that you can or even should do anything about it. I’m just saying it’s true. If you survive on your own for too long, you become unemployable. Well, maybe you can jump into something else entrepreneurial, like somebody else’s startup. But normal employers won’t want you.

I had 12 years between my last real job and my own company getting stable enough to write regular paychecks. I survived with consulting and authorship.  In the beginning I’d get regular calls from headhunters, but after a while they stopped calling. The last real job offer I got came about halfway through that period.

I’m not entirely sure why. Maybe entrepreneurs are too independent. Maybe they’re not good at taking orders, or playing well with others. Maybe they suck at office politics. This isn’t my expertise. If you really want to know more about this, ask somebody in HR for a big company.

(image: my modification of an image by winston link/Shutterstock)


  • Yang Zou says:

    I am in the same situation now. Being an entrepreneur for 5 years in another country and then spent 3 years to pursue a graduate degree in US after my company was merged. I haven’t been employed for 8 years. Now I am trying to find a new job in US in the same industry. However, there’s no big company willing to give a chance to interview me.

    I think discipline & control may be the top reason. Entrepreneurs normally have their own methodologies to solve problems and they are more result oriented. However, follow the instructions and procedure is the first priority to hire a new employee for most employer. It is a confliction situation between change and be changed that entrepreneur employees may influence the company culture rather than be influenced.

    It is possible that only small or new business companies are likely to hire entrepreneurs.

    It’s a comparable situation in most businesses and industries. Think about it, your company is manufacturing a kind of product and most of them are on average quality. The company will abandon the defective ones for sure. But how to deal with several ones in exceptional high quality? For a matured product, these exceptional high quality ones will be eliminated as defectiveness, otherwise, the company have to upgrade the quality for this specific product line, which is costly. However, for a new product, these exceptional high quality ones could be samples to promote in the market, compete with rivals and help to increase the market share.

  • Ian says:

    Thanks for putting into words what i’ve been thinking also, Drewry. I’ve had a lot of people just lose interest in me because i stopped making money. They loved me on the way up, but most of them kept going up and i started experiencing work struggles. I hope i’m not unemployable. I don’t enjoy being a lone wolf. I think having a tribe is critical to being socially normal. The only way i’ve been able to deal with all the pain is by shifting my attention to God and listening to Dallas Willard lectures on Youtube.

    P.S. I don’t think it’s ever too late for anyone to become employable. However, i think we’d have to get out of our own way enough to be an asset to someone else or another company. The problem might be that we only want to live life on our own very strict terms. We entrepreneurs could use being a bit more flexible with our rules for what constitutes freedom, contribution, and significance. Cheers everyone.

  • Isaiah says:

    Tim you are very right. It so difficult for a genuine entrepreneur to work under somebody and for me I find it very difficult. Thanks for your write-up.

  • Cubby says:

    I don’t believe in the word “unemployable” unless you have a prison record. Strangely enough i’ve heard there are jobs for prisoners after they get out! The point is if you were one of those types that gets into it with your boss, or has a high level of pride and ego, it doesn’t matter if you work for someone or for yourself. You are a limited in your success. Self improvement and growth is the key……or rather understanding people and how they work and think.

  • Samuel says:

    Am almost heading out………..full story in 3 months time

  • Drewry says:

    this blog post this great inspiration to me, as I know firsthand myself I am “unemployable”. The awesome life challenge of not being able to accomplish gainful employment in working for someone else is what motivated me to go abnormally the extra mile in [being my own boss] and “starting my own business”. It hurt when a lot of people walked away from me and passed judgment because I could not get a job, and the situation in life I faced. I’ve had people even promise me things, turned around and emotionally slapped me in my face, while showing me a very dark side side of their personality. people like that motivated me to “rely on God”, because [Christ overcame everything in the world], and knowing everything I experienced in the past and up until today is nothing more than a test of what I am spiritually made of…

  • Rob says:

    I AM unemployable! Here are the symptoms:

    I worked in the same company for 27 years and became completely institutionalized.
    I was made redundant at 48. I walked away with a cash package and didn’t even empty my locker or turn up to the leaving party.
    I’ve three times in my life, dropped my address book in the trash and started again.
    I’m best friends with people for 20 minutes, then I can’t trust them.
    I am a perfectionist. You will never be able to do it, the way I want it done.
    I am an inventor. I am a dreamer.
    I haven’t paid income tax for 5 years. I will never pay income tax again….. ever.
    I don’t read, listen to music, or I have any interest in current affairs.
    I am not a team player.
    There are no lighthouse keeper jobs anymore.
    I hate children. Especially, if they’re in the same restaurant as me.
    I hate bad parents more. Especially if they’re in the same restaurant as me
    I emigrated to a country where charity work and religious involvement are almost compulsory. I am completely critical of religion and charity work.
    My parents divorced when I was 3.
    Apart from good cooking, I’ve had virtually no parental support.
    I have had virtually no education.
    I have no qualifications at all.
    My two children are at university and doubtless will qualify highly. They’ve never failed at anything, ever. We love each other but barely speak.
    I have met my true soul mate. We shun other humans.
    I’m disappointed in life. I can’t help it, I just am.
    unbelievably, I’m completely positive about everything.
    There is no such thing as luck.
    I write my own future. I think it so….. and it is so.

    I AM unemployable! I have no idea what’s next.

  • Richard says:

    I am a bit of a late comer Tim, but this is an incredibly important topic. I recently took my first 9 to 5 job (with the government) at the age of 50. Like many who have commented here, I am trained to survive in many environments…except a 9 to 5 job..with the government. For the first time I have realised I am not of corporate blood and will probably jump ship, purely because the decision making and productivity is so slow that I can see my life draining away for no purpose. The question is, have entrepreneurs like us created our own self destructive little world where comfort is living on the economic edge?

  • Meaningful Work | Guiding Vision says:

    […] about six months of job hunting I’m starting to think Tim Berry is right: entrepreneurs are unemployable.  In many respects I’d much rather work for myself.  Flexible schedule, I call the shots. […]

  • Tracy says:

    Thank God I didn’t read this post before I jumped off the employed diving board into the entrepreneurship waters! 😉

    Having taken the swan dive and seen it turn into a belly flop, I’m still ecstatic I took the dive. I’m currently what some people would call “employed” but as a commissioned sales position. The corporate mentality of my employer drives me crazy. I find ways to make it work, but once your mindset is all about quick and nimble solutions, it’s hard to “go back[ward].”

  • Brian of DomeApparel says:

    I just copy and pasted the word “entrepreneur” because my spelling sucks, but I have no plans on teaching a spelling or English class anyway so sue me. I started a Tshirt company after my previous position as a web designer for an onlnine lead generation company no longer needed my services. While there I was for sure happy with the paychecks but at the end of the day was not 100% content. As explained in the post I felt that if I got too comfortable in my place it would ruin my aspirations to want more. (will explain “more” later below)

    I often found myself having ideas surging about other possible business opportunities and even inventions in the middle of my workday, 1ish – 2ish. They didn’t distract me from the work I was producing partly because I’m very critical of my own creations and work produced but did realize I was never completely at “home”.

    One day after the company merged I was in a trendy office workspace in SoCal kind of Google-ish/like I believe was their intent, and the new boss was explaining the bonus program which had a 10% (anual) of salary cap that would change after 10 years of service to I think 15%. 10% yearly breaks down to 2.5% per quarter, no bueno. I wanted to fall out of my chair (laughing).

    10 years made my head spin. If I didn’t have something going on in 10 years I must be dead was my thought. The thought of having my financial growth potential capped was just crazy to me. People / employees need to be rewarded for their efforts and contributions. It’s like office space and now your goal is to do just enough to not get fired, which is never good for a company. That’s why service sucks today, nobody is a skilled professional or getting paid enough to perform better (in general). How many times have you found yourself telling a salesperson more about the product they should be selling you?

    So “more”, the company eventually went to shit and the old entrepreneurs I worked for started another company and I worked with them until the day came when my services were as stated before no longer needed. Not what I had in mind. I was hoping to have one of my side projects pick up to a point where I would be able to leave and help them find my replacement. But what’s over is over. Wanting “more” wasn’t always a financial thought but the “ability” to make more was. With a 10% cap it was not possible to make more. But having your own business anything is possible! It doesn’t matter if it isn’t probable in the mind of entrepreneurs because possible is a better thought. That’s what I want and what makes me happy. Will I be the next Zuckerburg from a Tshirt company? Probably not, but it does fulfill my want to create and operate and hopefully give some other people, friends, or family a place to earn an income while not being in too much of an uptight environment.

    I read the article and realized I may be unemployable and I guess that’s all the more reason I need to stick to my grind and try to control as much of my financial life as possible. Do what makes you happy.

    Oh yeah if your interested check out the brand I created “Dome Apparel”. The logo is a big brain which represents creativity and out of the box thinking and the tag line is “Creative Minds & Grinds” or CM&G abbreviated. That means be creative and you can make a come up. Be positive.

    sorry for the rant, but the article made me do it 🙂


  • Tim Berry says:

    Again, thanks for the comments, and I’m noticing two interesting subplots here, in the comments:

    1.) The “not me” theme; “that may be true, but it doesn’t apply to me.” And I’m not saying it does, either. I can except the exceptions to the rule. And you, if you choose, can be one. That’s for Chris, Amber, and others here …

    2.) The “and hooray” theme. We’re unemployable, and, like Joel says (thanks Joel), proud of it. Jon, Joel, others. Maybe the reason we’re unemployable is that we’ve seen the light, like it better on the other side, and don’t want to go back.

  • Joel Libava says:


    Spot on! I never want to work for anyone else again. Ever.

    (Unless I have to.)

    I’m totally unemployable, and proud of it!

    The Franchise King®

  • Jon Buscall says:

    I think I realised this a couple of years ago. Mind you, I don’t think it’s necessarily a bad thing. As long as my own business survives.

    The entrepreneurs of today are the employers of tomorrow 🙂

  • Adrian Dayton says:

    This is an interesting post. I lost my job working as a law firm lawyer almost 2 years ago and have since built up a thriving consulting business and I often wonder, “would I ever go back? could I ever go back?” and it doesn’t seem very likely. I’m addicted to the freedom and the ability to make changes and adjustments quickly to my business model. It would be much harder to be a “full time” employee.

    It would seem though that sales jobs would be a piece of cake for an entrepreneur to secure, especially is they had strong sales as an entrepreneur. I guess the big question is, do true entrepreneurs really want to work for someone else after having that freedom?

  • Scott Asai says:

    I agree entrepreneurs are a different breed. Once you have your own business and realize that’s the environment you desire, it’s very hard to go back.

  • Tim Redpath says:

    So true. I have been independent for 8 years and I find it harder and harder to imagine myself permanently in cubicle land. Short contracts are fine but not a life sentence.

    I find the longer I work alone the more potential clients understand that I am not looking for a job. If they are looking for consultant support, they want someone who is focused on their deliverable and will work until the project is complete.

    Thanks for sharing.

  • Mike says:

    Im here to tell you Tim is dead right. I built a reasonably successful business over a period of 8 years and sold it about 5 years ago.

    Despite spending 5 years working for Hewlett-Packard before that, running one of the biggest channel roles in the country and also one of their product lines the only jobs I have been able to easily slot into were startups that wanted someone entrepreneurial and a commission only role selling, I was never able to get myself into a Corporate gig, I just didnt fit the profile. This is despite having demonstrable skills in Financial Control, Sales, Marketing, Online lead generation and the million other things you need to run a business.

    If they were hiring for a marketing or sales role, you had to have 5 years just doing that in a similar big company.

    I think the problem is that they need to employ people like themselves, if you dont fit the box exactly, you are not cubicle material.

    However they may be doing you a favour as the entrepreneur would struggle in these arrangements, all my friends who sold businesses (I was a member of Young Entrepreneurs Organization) none have been able or wanted to go back into corporate/job scenarios.

    The only solution is to get back on the horse and go again, I must say though its much harder the second time around. Any similar experiences?

  • Pam Lawhorne says:

    I agree entirely! I think it may also be that they are not willing to take a risk…

    In this economy, most employers may have concerns that when the “shift” takes place, the people that they had invested time and resources into training (as one of their employees) will go back to being self-employed. It simply makes more sense to go with someone who is more “stable” i.e. someone who’s worked for a corporation all of their life!

    Great post! ;o)

  • Amber Wallace says:

    I have to say I agree with Chris that this isn’t always the case – I think work experience is important, but I think all interviews and hiring scenarios (at least when you’re an unknown candidate) have to do with how you present yourself. If you are applying for a non-management position and seem impossible to manage, that could be a problem! But that’s a problem no matter what your past experience is.

    In any interview scenario it’s important to tailor your discussion to how your skill set works for what that employer needs — in a sales position, talking about how you as an entrepreneur increased sales 200% by doing X, Y and Z,and how similar strategies would apply to that company might be very useful. And the entrepreneurial drive can be an asset to many companies, as can the often diverse skill set that often comes with starting/running a business.

    Depending on the position, I do agree there can be a threat factor. Not necessarily that someone will run off to be a competitor, but that as an entrepreneur you might shake things up (hopefully this is an asset, but you never know), or expect to move up quickly, or want to do things “your own way.” But I think these concerns can be overcome as well. And at some point, if you’re assets aren’t a good fit all around, and you absolutely won’t be appreciated, it probably is best to look elsewhere!

  • Dave says:

    To my earlier comment I should add that entrepreneurs may have job prospects with client firms, good friends or someone else who already knows them well. Their chance with strangers is very remote

  • Dave says:

    I’ve been an entrepreneur for about 25 years. No great business, just a solid consulting practice. Five years ago, my field was dwindling away due to market changes. I had little interest in starting over, so I spent (wasted) a year looking for a job.

    The jobhunt folder from that time has about 1,500 emails in it. I had vice presidents from seven substantial companies say, “We need someone like you. I have to get you in to talk to people.” I got one interview. The other leads were all shot down internally before going anywhere.

    Whenever you hear a corporate leader say, “We need more entrepreneurial types in the organization,” don’t believe it.

  • Greg Womble says:

    I am a small-business entrepreneur with heavy marketing and content-development experience. My most recent venture, a one-man marketing agency, tumbled into oblivion in early 2008. Two years and several bone-headed career moves later, I decided to fight my generalist tendencies and enter the “straight” workforce as a specialist: corporate copywriter.

    Far from an arbitrary choice, it’s what I’ve always enjoyed the most about the marketing world, and I’m pretty good at it. I was lucky to land a job at a growing company that valued my diverse business/marketing background. I was also able to have an early, frank conversation with my boss about the restlessness that invariably comes when serial indies like me start working for the Man.

    My suggestion to fellow entrepreneurs: find your specialty, build another resume around it, and sell it hard. To paraphrase
    George Farquhar, “Necessity is the mother of re-invention.”

  • Sal says:

    Companies are reluctant to hire someone with the entrepreneurial ‘bug’ since they know that they will spending their free time working on something else and will leave the company as soon as they come up with something that works. Corporations want people who dedicate themselves to being shills and technocrats. They don’t want free thinkers and self motivated people, even though many corporations say they do.

  • Doug Keith says:

    Great post, Tim. I’ve worked in the both the government and corporate worlds for more than 20 years, with my last position being a VP in a large global organization. But three years ago, after searching high and low for the “next” thing, I decided the ONLY thing I could do was go out on my own.

    And now that I’ve been out here by myself, I realize that it’s not the employer that won’t hire me that’s the issue — it’s me not wanting to be hired. I think I would have a very hard time going back to the endless meetings and 1K+ emails every day. I swear that I wasted 40% of my time every day when I worked for someone else, and now I think the trade-off for the steady paycheck isn’t worth it.

    So while I think I could still handle an interview well and do a good job of selling myself, I don’t feel like it. 🙂 And that would be likely to show through — as it did when I interviewed entrepreneurs for positions in my old company.

    P.S. I don’t believe there’s such a thing as a “9-5” job out there anymore. It’s become routine for employers to expect availability practically 24/7. So I’d rather put my 50-60 hours a week into myself than someone else’s business.

  • Chris Parsons says:

    lol, I just did a post about why this isn’t true…


    Basically, I think that many Entrepreneurs lack the ability to get things done in a large organization because they don’t understand or care about politics and tact. Thus, they’re better suited for owning a business where they get to make all the decisions.

    But just because you suck at this doesn’t make you an Entrepreneur, and if you happen to be good at it – it doesn’t mean you aren’t meant to be an Entrepreneur.

  • Ann says:

    In my traditional job life – I have to admit it was a major concern to hire a entrepreneur. The thoughts behind the hiring manager/managers is that you used to freedoms you might not have, you are used to being the boss yet you’ll have to be reporting to someone in the corporate enviroment..
    If the position is in a business development or the director over a start up department the skills of a business owner are a fit – again there is always a concern your’ll stay put.

    Now that I own my own business and we’ve hit a hard year. I have a renewed concern/outlook on this topic.

  • Tim Berry says:

    Thanks all for a really useful collection of comments here. Chris, you’re more than welcome to disagree and the way you put it, focusing on the exceptions to the general rule, makes perfect sense to me. There are always exceptions.

  • Nick Casares says:

    I agree with Daria’s first point. I think entrepreneurs are so used to wearing multiple hats that the concept of doing “one thing” feels very unnatural for most of us. It’s possible employers know this from previous experience with entrepreneurs making the jump to employment.

  • Kathy says:


    My first time to your blog, and I’m loving how insightful this post is. You are absolutely correct. Kinkos founder Paul Orfalea said he became an entrepreneur because he was “practically unemployable.” He’s not alone.

    It’s a common sentiment among established entrepreneurs. When asked in interview why they became an entrepreneur, the answer is not always that they wanted to change the world or an industry; usually it’s more about the fact that they knew they wouldn’t make it in the corporate world.

    Great post!

  • Kathy Bornheimer says:

    This issue can be very complex. While I agree with most of the comments; stealing company ideas is not one of them. Employers want to maintain the majority of control; Entrepenuers won’t be contolled.
    Employers would benefit from bringing Entrepenuers into their companies occassionaly for fresh ideas by an “outsider”. Inbreeding is occurring too often now. Corporate leaders should eliminate their “yes men or women” and have people that will speak the truth in their organizations. These relationship need only last a few years. The true Entrepenuer will be ready to move on by then and the employer will better for having them during that time.

  • M L Castellanos says:

    Wow! I hadn’t thought about that! For me, I was under the impression it was a combination of demographic (perceived age and descent) and too experienced. That said, I am fairly convinced the hiring managers (yes, even CEO’s) are scared silly of hiring someone who undoubtedly will come in get things done leaving no excuses for why tasks had not been accomplished previously.

  • Chris says:

    Tim I respectfully disagree, it all depends on your attitude and how you present your qualifications to your new employer. If you act like an insubordinate Type A who can’t take instruction then sure, they don’t want you- no one does.

    But if you can confidently demonstrate that you went out there and blazed a trail, grew an organization from X to Y in revenue or projects you are immediately at an advantage in my experience. I think if you put a search plan together and were proactive about it (rather than waiting for commission headhunters to call you) you may think differently. Great blog BTW.

  • Anon says:

    David– 10-20% annual raises? What decade are you referring to?
    Most are lucky to get 3-5%

  • So you want to be an entrepreneur? Starting a business thoughts | Paul Wallbank says:

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  • Ivan Walsh says:

    I think David’s on the right track with 2) Fear that they are more likely to steal ideas and start a competing business.

    The other is that there is often an anti–establishment element in Entrepreneurs, which is never going to work in a corp environment.


  • Daria Steigman says:

    Hi Tim,

    I’ve been noticing this myself the last 2 years as the economy dipped and more small business owners looked for the stability of a regular paycheck.

    I agree with David about the stop-gap concern, but I don’t think it’s just that. Entrepreneurs may work in teams, but they’re also used to leading them–and demonstrating you can fall in line behind someone else’s leadership can be a challenge.

    Two other quick thoughts–

    (1) The difficulty of defining core strengths (okay, this isn’t unique to entrepreneurs, but I’ve found many have a harder time honing in on the their unique selling point as an employee).
    (2) Adjusting expectations (especially in this economy), so you’re looking for the right job and not the perfect job.

    Just my random thoughts. Great topic!


  • David Petersen says:

    Two primary reasons why entrepreneurs scare employers:

    1) Fear that this job is simply a stopgap for them and they won’t be happy in the long run. Your typical corporate employee is happy making 10-20% annual raises, enjoys the security of a guaranteed paycheck and the ease of life from a 9-5 workweek. An entrepreneur doesn’t want this this. He wants greatness.

    2) Fear that they are more likely to steal ideas and start a competing business.

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