In the November 29, 2011 Ask The Headhunter Newsletter, a reader who’s run a business for years wants to know whether it’s true that the self-employed are unemployable.

I was on a discussion forum today where the consensus is that you’ll never get hired if you’ve been self-employed. Is that true?

I have had my own consulting business for the past 19 years. My original client base is drying up, but happily I have had some luck with a new market. I can definitely stay on my own, and there are good reasons to do so. BUT… I have not explored many job options over the years. Lately I have seen friends & neighbors get good-to-great jobs, things I would love to do professionally and personally. New challenges, terrific companies… and I find myself envying those folks.

I have been going on some job boards where I’ve seen jobs I would love to have. I’ve studied your approach and I feel confident that I could make good contacts with good companies. I know I would be a great, business-enhancing employee.

Then I came across that discussion forum today. Would it be hopeless for me to even try now? Given what you have written across-the-board, I feel like that forum’s assertion can’t be right. But I figured I’d rather ask you before embarking on a doomed-to-fail effort. (The people on the forum suggest all kinds of subterfuge to hide the “shame” of self-employment. I am very much against subterfuge!)

I have also read that people will “never get hired” if they’re over 50, stay-at-home moms, job-hoppers, or felons (!). I figure that, with the exception of the felons, there must be plenty of people in those categories who get good jobs. Yes?

Here’s the short version of my advice: (For the entire column, you need to subscribe to the free newsletter. Don’t miss another edition!)

My Advice

I’ll tell you what I said to a young man I know who is applying to colleges. He wants to study physics. Princeton is virtually impossible to get into and everyone has told him not to bother. But he wants to go to Princeton.

I told him that if you want to do something, then go after it like it’s the only thing in the world. Your goal is to succeed, not to worry or even to think much about the so-called odds. And you certainly should not listen to the comments and speculations of people who are afraid of failure.

Odds matter only if we’re talking about a population of people, because odds are descriptive of a population. They don’t matter much when we’re talking about an individual. Odds don’t prescribe the right action for an individual. That is, just because Princeton rejected 20,000 applicants is no reason not to apply. What matters is what one person is capable of doing — and what he’s motivated to do.

So, ignore and stop reading that stuff on the forums. Do what you want to do. Do it the best way you know how. People with their own businesses get hired. I don’t know how many, and I don’t care. Even if every single one of them has failed to date, your objective is to be the first one to succeed. If you think you can be a great, business-enhancing employee, that’s what matters. It’s better yet if you can demonstrate those qualities. That’s what will get you hired.

My advice is to ignore everything you’ve been told. Then go do what you set out to accomplish. Either smile or smirk at the naysayers. They don’t matter. They’re pretty pathetic. Failure in America is built upon their fears and chatter.

A 63-year-old reader told me last year she’d landed the new job she wanted — in part because she ignored all the discouraging things she’d heard about age being a obstacle. The young man I mentioned applied to Princeton. Will he get in? Will his outcome affect whether you pursue the jobs you want? Go for it. Stay away from the “You can’ts.”

Did anyone ever tell you you’d never get hired? What’s the secret to success in a “lousy” job market? (Hint: There’s no such thing as a job market.) Tell us what you’ve pulled off in the face of incredible odds — that’s what matters.

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  1. While I agree with the principles of your pep talk, having been self employed since 2008, I also understand where the discouraged job seeker is coming from.

    Reading your newsletter has taught me to aggressively protest my right to not disclose the hourly freelance salary (which was carefully researched and based on the 2012 Writers Market Averages) to prospective full time employers.

    Correct me if I’m wrong here but no hourly self employed salary will make sense to a company looking to fill a full-time freelance position. Reason is that generally those positions are only deemed “freelance” for purposes of denying benefits. If you are NOT having to devote time to market yourself and manage client billing because a company takes care of that, you’ll be expected to charge less. At least that’s what I’m assuming based on responses I’ve gotten from prospective employers who did actually manage to shake a salary quote out of me.

    Nick, I believe anyone in the same boat at the person who wrote you the letter –ie a self employed person looking for full time work– would appreciate any strategy you might have to offer in addition to the pep talk.

    I try and focus on the position and how I can uniquely help a prospective employer get from point a to point b. I also provide a four minute slideshow portfolio of project I’ve done in my freelance work.

    It is, nevertheless frustrating to know how much weight a “self employed” history has to an employer. I generally give interviewers an honest answer when they ask me why I want a full time job now. That honest answer is, “I’d like to be able to work 40 hours a week rather than 80 hours a week” (which happen when your job is so dependent on finding your next gig).

    The gap can be bridged but its still there.

  2. I couldn’t agree more with Nick (and used it nearly 30 years ago when wanting to the join the Portuguese Air Force as a pilot trainee ;-) and disagree with Susanna.

    The person having written to Nick has been, supposedly happily, self-employed for 19 years. He/she now sees opportunity for being even more happy (hope I’m not making any short-cuts ?!) whilst bringing business value to others. In my view it would be easier to explain 19 years (which should indicate a choice) than a much shorter period (which COULD indicate an obligation).

    Go for it, show your value, and be hired!
    Easier said than done, but one cannot succeed without trying ;-)

  3. I am self employed. I have heard some of the same type of general talk regarding switching to an employed status. What I have found is that folks are usually saying it is hard and more difficult in some circumstances to find employment for a self employed person. This is more common now than ever, something is hard or takes a special effort to achieve and therefore it is impossible or can never happen.
    Focus on what you know you can provide in terms of value and avoid HR, then you will likely be successful in what you attempt.

  4. First day at a new job, 10 years ago, another new hire beside me had just been self-emplyed. So it could be done at Y2K times. This was a great company with an open kind of mindset.

    I agree with Nick’s advice. Use your network, and go for it.

    Have fun in the process.

  5. If you let nay sayers on job board forums guide your job search, then you’re spending too much time on job board forums.

    Also, while you might consider yourself self-employed, you probably had a legal entity that you worked for. It might be (or have been) a sole proprietorship or a LLC. This is the company you should represent as your employer, because it was. Just because you happened to own 100% and were the sole employee, doesn’t mean you need to describe yourself as self employed. You should focus on what you did for your customers and how you delivered value to them and your company.

    I always go back to Nick’s basic advice, during the interview demonstrate how you would do the job the hiring manager is hiring for. Demonstrate how your past experience can be applied to the job at hand.

    As someone who has hired hundreds of people over the years, I like people who have owned their own business. They bring a broader perspective to the work they do for our customers. Our customers appreciate the experience.

  6. After working in my own company for 12 years, I got hired by a major large corporation after I decided to go back into the corporate fold. I’m 48. My wife (51) got hired at the same company. It happens. Perhaps if the hiring manager can’t see your worth then you just don’t want to work for them anyway!

  7. This is similar in a way to those who say they can’t go back to school because when they finish their coursework they’ll be 60 or 55 or whatever age appears to be a problem.

    The response to the above objection is that you’ll be whatever age anyway – so go and DO IT!

    You have absolutely nothing to lose in trying your best. You’re still self-employed, which is a lot more than some others have.

    • My thoughts exactly. I can be whatever age I’m talking about and going after what I want, or be that age and not. Guess what I’ll do?

  8. I’ve hired several hundred to a thousand people over the years including many that have been self employed for multiple years.

    The issues never been self employment. The issue is do you have the skill sets that I need for that job, do you fit in the culture of the company, and can you grow over time? If the answer is yes to all of the above, then your in the consideration set. If the answer is no to one of these, then your not.

    And just as a note, I work for a Fortune 300 company, have employed people in good positions with college degrees, without college degrees, hired women who took time off to be stay at home moms and re-entered the workforce, and self employed people.

    In addition, I also ran – at one point – the college recruiting for the company on top of my regular duties – so I have experience with new college grads, grads going back to get advanced degrees, folks getting out of the military and getting degrees – basically every kind of background you see in business.

    Getting through a restrictive HR is an issue. On average, we get 500 application per job posting. So HR gets very picky on the 10 or so it forwards to the hiring manager. In your case, making one on one contacts will be important.

    But a GOOD hiring manager will not turn away good talent. No applicant is perfect.

    Good talent is hard to find. And the general rule I use is that if an applicant has 75% of skill sets I need and has a lot of talent, a willingness to learn, then I can teach him the rest in less than 6 to 12 months. And the investment worth it to me.

    If its what you want to do, go for it.

  9. I agree with Nick.

    The job market is tight and both companies and discouraged job hunters can identify loads of reasons not to hire someone.

    However, while some issues may indicate problem employee (like felon, for instance), I don’t see what problems the self-employed intrinsically present as employees.

    Except that if the job turns out to be horrible, the individual can jump right back into consulting instead of shuffling and grinning until he has the numbers for retirement.


    Diana Schneidman
    Author of Start Freelancing And Consulting: How to take control of your life and make great money quickly as a solopro

  10. A few thoughts, gathered up in a list:

    1. An employer who hires a successful self-employed person should make sure the job includes some kind of project management. By definition, that’s what makes most self-employed people successful. And as the job hunter, I’d emphasize that and I’d perhaps avoid jobs where it’s not part of the work. You might hate that aspect of your self-employment, but if you’ve been successful, that’s probably one of your strongest suits.

    2. Susanna makes good points, esp about showing how you’d take it from point A to point B. (See #1 above.) Sorry this column was more “rah rah” than specific suggestions. Sometimes I think rah rah is what someone needs!

    3. Employers often regard self-employed folks as head-strong and set in their ways. The candidate’s job is to show how that will benefit the employer. There’s also the view that you’re going to leave to start another business, or that you’ll want to call all the shots. Again, it’s up to the candidate to address this. The biggest mistake employers make is that they often avoid these issues rather than address them head-on in the interview. So help them out.

    4. Thanks, Jamie, for explaining how some employers view self-employed people. I hope there are more like you out there!

    5. CJ’s bottom line is important: If they don’t want you, then it’s probably not for you. Walk away.

    6. And Don Green says it all.

  11. Horse hockey! Self emloyed people have plenty to offer and it is well received. I was just hire by the company I wanted making more than expected and after 10 years of being self employed.
    STOP listening to the negatives. Follow Nick’ s guidance on pretty much everything. I interviewed with about 18 people in 6 companies and they all saw the exceptional benefits of hiring somebody who was self employed. Especially if you have done it for a few

    Even if you look the basic problems companies have with new employees that you have proved are not part of your fabric.
    – You work unsupervised
    – You take on more responsibilities others avoid
    -You are financially responsible. ( every business owner knows how to save money and understands cash flow)
    – You respect and understand all aspects of what makes a business work and the value and needs of various departments. This is very important.
    -You are not afraid to do the crappy little jobs yet have the ability to to communicate, sell and service your best clients.

    Those are just a few suggestions. So slap the “woe is me” out of yourself and find a deserving company where you can maximize your strengths while maximizing their profits.
    A primary rule of sales is to stay away from the negatives. Job boards are the negatives with pretty packaging.
    They make you feel optimistic but then after awhile they make you feel worse as hope and dreams get brought out and crushed. Delete them ALL of your computer and reread Nicks advise and blogs.

  12. “Hide the shame of self-employment.” That was classic and illustrates the core problem. I guess that Steve Jobs, Bill Gates and Donald Dell should be ashamed of the millions of jobs they created because they were self-employed from a young age…

    The problem is the factory mindset, as Seth Godin has noted in his books, by most American hiring authorities and employees. A self-employed mentality does not add up to them. For as much as firms and their recruiters seek those “who think outside of the box,” they don’t know how to utilize such people who refuse to punch a clock or follow strict guidelines better suited to a century ago.

    If you ask me, we are all self-employed, but the freelance mentality is punished in a country that was founded on taking risks. The majority want security and factory work. Both don’t really exist anymore but the mentality is etched into stone, unfortunately. When an individual such as the protagonist in our discussion decides to “step back,” he experiences resistance, ignorant questions and suspicion.

    My advice to the reader: Stay self-employed. Use your entrepreneurship and considerable skills gained over 19 years to create another successful business. Your neighbors and friends have “temporary jobs” that could vanish tomorrow. You actually created something of value by taking risks. They should envy you; not the converse.

  13. One thing the letter writer is doing wrong: looking at job boards. S/he should ignore them completely, both their ‘jobs’ and their advice, and concentrate on talking to those “friends & neighbors” who got “good-to-great jobs, things I would love to do professionally and personally”. The more s/he learns about what those people are doing and where, the closer s/he’ll get to good hiring managers.

  14. I have to conjure up the old adage my mother used to use: “Hope for the best and expect the worst.”

    I agree with Nick’s advice that the guy should go for it and not let the “odds” or naysayers deter him. However, the guy needs to be realistic—the reality is that there is a tremendous bias against hiring consultants as full-time permanent employees. Therefore, he should have a plan and some idea of how much time and energy he wants to spend, especially in terms of lost opportunity costs with current and potential clients with whom he has a track record. He also may want to give himself a set timetable for how long he focuses on finding a job before he returns his energies and focus back to his own practice for long-run sustainability.

    I also agree with the people who said they would like some practical guidance on how to make this transition. Two final thoughts:

    1. He may be better off looking at smaller, entrepreneurial companies, rather than larger corporate environments—they may be more open to hiring freelancers, and he might fit better into their more informal cultures.

    2. He may find that HE doesn’t like working for someone else. I started my own consulting practice a year ago—the money sucks, but I love the independence and lifestyle, and for that reason would likely not be interested in a job.

  15. I don’t know about being self employed but I do know about ignoring the nay sayers. I started night school in my late twenties and people told me I was wasting my time because I would be 40 years old by the time I graduated, and who would hire a 40 year old just out of college? When I shared this concern with my boss, he said I would still be 40 someday with or without a degree – which one did I want? He was the smartest and the most generous person I have known, not only did he encourage me but he taught me how wrong it is to discourage others. He used to say “if you don’t ask, the answer is always going to be ‘no’.”

  16. @Charles L: Now we just need to get more employers to see your points. Maybe send them the link to this discussion!

  17. I have also read that people will “never get hired” if they’re ——— with the exception of the felons.

    I know of an old felon getting a job, albiet a low level job because he is working through a “transitional assistance”program. He has a “rap sheet” to prove it and therefore is a known entity to the employer, while the rest of us without rap sheets are a risk because they can’t easily “find” anything.

  18. I have owned my own architectural/interior design business since 1985 and am over 60 years old. Due to decreased work load, I find myself in the position of trying to find full or even part time work, either in my field or out and have submitted cover letters, resumes and applications to a variety of companies, all have gone un-answered. All of these attempts indicated I own my own business, hard to hide when is the only thing having done since 1971. I discussed with local employement counselor who said I would NEVER get hired if I showed self employed or owned my own business, and suggested instead to state that I was the “business manager” or “office manager” instead. Maybe I am naive, old fashion, or just stupid, but that does not seem righ to me. Sounds deceitful to me and that is not my way. It is difficult, but not impossible, to have been in one profession for entire career and then expect anyone to accept all those years of experience in some other field. Is a very disheartening situation to be in.

  19. To succeed at achieving any goal — large or small — requires a variety of things.

    One of which is: “Focus on all the reasons TO do something; rather than all the reasons NOT to do something”.

    Otherwise all that you will succeed at… is failure.
    Every time.

  20. Excellent column. I have had numerous employers tell me they are skeptical about prospective employees who have been self-employed. Their concerns are two-fold:

    #1 – There is a fear that if a person has a history of working for him or herself, they may decide after being hired to go back to their own business, leaving the employer in the lurch.

    #2 – People who are self-employed are used to doing things their own way and will resist doing things the company way.

    Note that these are concerns. They are not written-in-stone objections.

    I coach clients to be aware of and gracefully address these concerns in the cover letter, resume, and/or the interview, but to NEVER let it intimidate or deter them in applying for a job they want.

    As any successful sales representative will tell you, objections can be overcome. The main thing a hiring manager is looking for is is the value an applicant brings to the table. Clearly demonstrate and quantify your value. If you do that well, concerns about self-employment will fade away.

  21. After being self employed for most af my life (I started in the family business as a child). I decided to make a change. At 50, I took a job in Facilities Admin. at a large university.
    Nick’s advice is perfect. If you really want it, get out of your comfort zone and go for it with all your resources. And you know what? You’ll eventually be just where you want to be.

  22. The secret to getting in the door remains a mystery to me. When cover letters, resumes, phone calls go unanswered, gives the impression of non interest. I have been involved with a local head hunter, whose standard report is “no one is hiring”.

  23. When I asked Nick this question, I was heartened and so encouraged by his non-advice (!) advice.

    May I thank you all here as well. Especially Steve Amoia. You have, to a man and woman, hit it on m-a-n-y heads for me, and I am absolutely going to take your wise counsels to heart.

  24. P.S. And special thanks to Tony too. Your story is fantastic. Congrats!

  25. I agree with Steve’s points. If it’s a ‘side biz’ you’re probably better off not discussing it at all with prospective employers. They say they want ‘entrepreneurial’ people in their job ads, but they don’t – they want opinion-less, mindless robots to do their crappy corporate jobs for them.

    Having been open about my side business in the past (which is totally auto-pilot) with hiring managers has gotten some surprising responses. Mostly jealously but also the fear that you will not be giving all your time, heart, soul and life to their job. This is reasonable to question which is why if it’s a side thing you shouldn’t mention it – the same way you wouldn’t mention mutual funds or apartment buildings you may own. Your entrepreneurial skills from running an actual business will far supersede those of a prospective hiring middle manager’s. Big problem.

    It is also a huge challenge to take direction from some middle management air head after running your own business. It’s just tough to do both.

  26. no apologies, a couple more rah rah points because they are very important in retooling one’s attitude and approach toward executing change. Yes, employers and would-be hiring managers are problems, often beyond your control. But you can control yourself. By that I mean as a recruiter I see a LOT of job hunters disqualifying themselves, not trying, not reaching, not following up, as the writer seems to be about to do, disqualify himself. These are things under your control and Calvin Coolidge’s quote fits my point & the discussion to a T
    “Nothing in the world can take the place of Persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent. The slogan ‘Press On’ has solved and always will solve the problems of the human race.”
    and some sports notary said something like “you’ll miss 100% of the shots you don’t try”
    It’s been suggested implicitly but I’d advise the guy to try some positioning. “Self employed” is like saying you found a job(s) for yourself. “Starting and running your own business” is like saying I provide goods or services to my customers/clients, just like any company you apply to does. Position yourself as a business owner.
    2. People who generalize that “no one hires self employed” are people who mean THEY don’t hire self employed, people over 50, moms returning to the market place etc. Pure uninformed, myopic BS. True that these situations do present challenges, but people who take them on and persist, as far as I’m concerned signal some guts and nerve, highly respectable attributes for developing a successful business. Why wouldn’t I want this in my organization? . So don’t hide it, flaunt it, market it.
    3. As someone suggested, try small companies, where the rigors needed to start and run a business will more likely be appreciated. People who grew up in large corporations live in their own world, nurtured by budgets, and layers of management, can’t possibly relate to the guts it takes to fly alone. You’re casting pearls to swine when you try to make a dent in their cocoons.
    I’m not pitching spin.
    I’m 72: Got this job when I was 69, my 4th over 55. We just hired someone who had her own business, I’m setting up an interview with my President with a guy who’s been consulting just like the writer for about 10 years. And I’m setting up an interview with a guy who really doesn’t seem to fit anything, but he doth persist and I like persistence. We have two people on board who persisted.
    We LIKE people who’ve run their own businesses because they can relate to running ours.
    Our company has 84 people moving toward 100. We do 15 million a year.
    So lay out a target, focus, take a shot, learn, do a post mortem, tweak your approach, and try again, again, again. Persist. If you persist it’s not a matter of if, just when.
    PS: I think we’re talking about former-felons, because Enron as an example many felons are employed, just undiscovered. As a recruiter I’ve place a former felon too.

  27. Many of my friends were small business owners and have closed up shop for a variety of reasons including being generally worn out, tired of chasing money, business or product is no longer profitable or maybe wanting some simplicity. Just like starting your own business is a personal decision, closing one is also personal. In your heart you will know the right direction.
    If it is to close up shop and move on, then do it with full blown enthusiasm. Focus on strengths, not what you can’t do. By the same token focus on companies or locations that see such value. Because of our individuality some are our strengths are also our weaknesses and visa versa.

    The Military is made up of ground troops, cannon, tanks, aircraft, ships, etc. Each element has different capabilities that can be perfect or useless based on the situation or battlefield. A tank won’t win a sea battle and a submarine won’t work in street to street fighting.

    Therefore, it doesn’t matter if it is a headhunter, job board or some other adviser that says nobody wants you because of experience, age , sex, education, etc. then stop using their short sighted, self imposed limitations(ie no long term vision) to pour water on your fire.
    Nobody is going to surrender a job to you, you must fight to get one where your battle design is best utilized.
    Remember there are people hiring right now that are looking for an employee just like you, but there is no magical matchmaker that will make it happen.
    Investigate, network, read, get or stay in shape, pick up the house, clean out the car and prepare for battle with focus.
    Remember nobody cares more about your sucess than you. Positive sells!

  28. I just read Don’s post. Bravo! Bravo!

  29. I had a client who had started and operated a business successfully for 10+ years. At the time he came to me, he was looking for a new challenge that would let him contribute as a senior manager in an established company. The point we came up with was that he had encountered many challenges during those years and met all of them successfully, amassing extensive expertise that would deliver potentially large benefits to an employer. He had basically “been there, done that” to the extent that he wanted to do in that setting.

    The approach worked for him–multiple responses, interviews, and offers.

    It might be tougher if the business is being shuttered because it has run into economic difficulties, etc., but there are still valuable points to be identified and communicated that could benefit prospective employers.

    You can’t please all employers, but as has already been said, you probably don’t want to even try! Some of them won’t be worth your time and energy.

  30. Don Green’s (and as always, Nick’s) are right on the Mark. I have been a Headhunter foor 30 plus years and almost always find hiring managers (not HR screeners) ready to hire the right person: someone who can do the job! Don’t let anyone discourage you from seeking out and finding what you want to do.

  31. Thanks for another great post Nick and Don Harkness. One thing that I have learned over the course of the past year plus since signing up for this newsletter is just how incredibly short-sighted and pig-headed many businesses, recruiters, and HR folks are. They wail about the lack of talent, but they persist in ignoring perfectly good if not outstanding talent even when it walks in the door and smacks them on the head. Why? Because they of their prejudices against the self-employed, against older workers, against the unemployed in a depression, against women, against minorities, against people who don’t meet each and every single criteria. They’re still looking for that purple squirrel. Why? I think it is fear of the unknown and laziness. Laziness because it is easier to pick a random criterion (no unemployed need apply; must have a college degree) to use as a screening out tool rather than taking the time to think about what the job requires and whether the person in front of them (or least their letter or résumé) could do the job with some training. Fear because they believe that someone who is self-employed would never want to work under someone else or can’t take direction without setting up an interview and finding out what that person can do for the company. They fear that the person will leave at the first opportunity. How do they know that ANYONE they hire, even the elusive purple squirrel, won’t just leave at the first chance of a better opportunity? They don’t, but it is easier to hold onto prejudices than to think and do their jobs (fill the position).

    I don’t understand the prejudice against the self-employed any more than I understand the prejudice against the unemployed, against women who took time off from their careers to raise families, care for elderly parents, in-laws, sick children and spouses, against those without college degrees, against those with college degrees, against those with more than 3-5 years experience, against those with less than 3 years experience.

    It seems to me that they are looking for excuses NOT to hire, rather than solve the problem for the company–fill the vacancy.

    The challenge is finding those who are willing to overlook these dings. Those who aren’t are helping with the self-selection process–they’re probably not good places to work, or maybe they are, but just not for me. There’s having a job, and having a job that is a good fit, both for the employer and for me. It has to go both ways.

  32. I concur, ignore the forum posts and concentrate on your belief in yourself. There’s a bit in a Moody Blues song (that may well come from other sources), “It’s easier to try than to prove it can’t be done.”

    It may sound trite, but it’s a good way to approach a job search. Don’t look for reasons to be rejected before you even get started — instead, assume you’re the best candidate for the position, and approach it with that level of confidence. Will you always get the job? Probably not. However, I’ve turned down more offers than I’ve missed, and the ones I missed were generally proven out to be a bad idea anyway. Or so I rationalize, which is fine in small doses.

    I worked for myself for a brief time, until I realized that IT consulting is tough when you can’t drive a car. (I’m legally blind, cool white cane, dark glasses, and the whole kit.) It took very little time for me to pick up another job, and another after that.

    As I tell young friends just starting out, “Don’t write the script in your head beforehand. But, if you can’t help yourself, make it a story of triumph, not one of defeat.” These are not simple platitudes, how you go into a situation has a great deal to do with what you end up getting out of it.

    And, as a manager, I certainly have no problems hiring people who’ve worked for themselves, often they are more mature and know what they want. One of my current team came out of self-employment, he’s an exceptionally hard worker and does not need a great deal of hand-holding from me. He also works well from home, and there’s nothing an IT manager likes more than someone who can take care of themselves and produce good work in the process.

  33. I loved Nick’s answer, as well as the comments here. What Nick calls “odds” I call statistics. Because I started my career late in life and have been successful (I’m happy and prosperous), I’m often asked to mentor people in their job searches. Without fail I tell them to avoid statistics because they don’t need a thousand jobs. Each only needs one. I’m older than all my colleagues, including my boss, and currently have the job of my dreams. I recently was offered, and turned down for various reasons, another dream job. I learned that if my age doesn’t matter to me, it doesn’t matter to anyone else either. It helps not being decrepit.
    Successful self employment for 19 years is one of the most difficult achievements I can imagine. A person who can do that can do almost anything. Negative “common wisdom” from the boards is nothing more than a group of people trying to feel better about its own failings: “If I couldn’t do it, no one else can.”

  34. “The Galleries are full of critics. They play no ball. They fight no fights. They make no mistakes because they attempt nothing. Down in the arena are the doers. They make mistakes because they try many things. The man who makes no mistakes lacks boldness and the spirit of adventure. He is the one who never tries anything. He is the break in the wheel of progress. And yet it cannot be truly said he makes no mistakes, because his biggest mistake is the very fact that he tries nothing, does nothing, except criticize those who do things. David M. SHOUP, General United States Marine Corps

  35. I agree that the formerly self-employed are often viewed with unreasoning suspicion, and I agree that the formerly self-employed are often overlooked gems as prospective employees. Has anyone addressed the difficulty that prospective employers may face, however, with VERIFYING our claims of experience, or success, or anything? They can’t talk to your former boss, after all.

  36. Jim, the self employed are either providing a service or a product or both. They have clients/customers. You verify self employment claims by reference checks…talking to their clients. Much like you might do if you were going to use their services or buy something from them. The boss of the self employed are their customers

  37. @Addie –

    Thank you for this … “Successful self employment for 19 years is one of the most difficult achievements I can imagine. A person who can do that can do almost anything. ”

    It really warmed my heart.

  38. After working in various public and private sector management positions for more than 20 years, I had my own company for 21 years. A few of those 21 years provided the highest gross income I ever made; others were on the opposite end of the scale. Along the way, I gained exposure to an incredible array of businesses and professions and was fortunate enough to work with people from a wide variety of nations, cultures, religions and experience levels.

    All of these elements have worked in my favor whenever I have had to supplement my income. While I’ve sometimes had my share of difficulties finding ‘regular’ employment, I don’t believe the cause has ever been my self employment. In fact, my background has helped me win several long-term contract positions.

  39. One of my sons had his own business for years, a mix of programming and imaging work. His wife now runs the imaging side profitably and he recently joined one of the top companies in that business at a fairly high level.

  40. There were many reasons I wanted to give up the freelance life; many of which people have already mentioned here.

    I got called in for an interview, and I’m really not sure why. They questioned me about my work, and then said that my experience was unorthodox. This is the weirdest part: people calling me for interviews when they didn’t like my resume. I had interviews with several positions that I knew I’d be perfect for, especially with my experience, but it seemed like the self employed part was a bit of a hurdle. I’m not saying that it can’t be done, but I’m saying that my experience wasn’t pleasant at first.

    Many of the people, in my personal experience, were looking for people to manage. I think they wanted to know that I was reporting to someone and being told what to do. They weren’t looking for someone independent, and it didn’t seem to matter if I was courageous and could bring in business and raise the stakes. In short, I don’t think they wanted to hire me for fear I might outperform them. Now, take into account that these weren’t HR types, these were just average joes looking for monkeys, and not corporate types. I wasn’t looking for corporate. This may sound lame but I want a simple job with responsibility. I don’t want to be taken up with worth anymore, but I’d rather have my day be done when it’s done – at 5 or whatever.

    This was just my experience, but I also reside in an area with a largely uneducated workforce. I should also mention that I managed to eventually land a job immediately after I modified my resume, and claimed my friend – who does some work for me – was really my boss. I also gave myself a phony hourly wage, and took off most of my credentials. Yes, I lied and got hired immediately. As soon as they realized I was just a common as they, I went on 6 interviews and was offered 3. And the other 3, well, let’s just say the interviews went way better than when people thought I was educated and ambitious.

  41. Good pep talk but by that reasoning I should buy lottery tickets.

  42. I really appreciate this article and the comments as well. I have been an entrepreneur in my own, successful travel agencyand then in Commercial Real Estate / Property Management.

    I wore so many hats as Director of Operations, Manager, Controller, Consstruction Propject Manager, etc. basically running businesses, for absentee owners. I’ve recrafted my resume and different versions for everything from QuickBooks jobs to Property Management positions.

    Any suggestion on two items?
    1> How should I craft my resume so that I look like I have more direction?
    2> How do you get around the required applications and the burning question of previous salary?

    Thank you very much and best of luck to all.

    • @M Hunnewell: I think your success lies in forgetting about your resume and thinking 100% about what a specific employer needs – and addressing that. When you hand a resume – of any kind – to an employer, what you’re saying is, “Here I am. Now YOU go figure out what to do with me.” Employers suck at that. You have to explain it to them/i> in terms of their specific business.

      That’s where resumes are goofy, silly, useless. A resume is about you. A job is about the employer. Address the job, not your history.

      You get around the applications by not using them. Why fill out forms when you can start talking to insiders who can guide you and get you in the door? There’s nothing easy about that – but there’s nothing easy about the job you want, either. So do the hard work of developing the contacts you need to create the credibility that will get you in the door.

      Resumes? That’s faking it. That’s relying on a stand-in. Employers don’t pay for stand-ins. That’s why most resumes are rejected.

      Thanks for your kind words about this article. Please consider all you’ve done. To accomplish each of those jobs/tasks, you had to configure your constellation of skills differently to address each one. That’s what it’s going to take to get past the guard at the HR door and the applications.

      Finally, the burning question of previous salary is bogus. Don’t answer it. It’s no one’s business. When an employer demands your salary history, it’s a tacit admission that it doesn’t know how to assess your value to its own business. Make them do it. Help them do it. I wrote a short book about this: Keep Your Salary Under Wraps. More and more readers take the advice and politely but firmly say NO to questions about salary. Imagine telling the employer, I’ll tell you my salary if you tell me the salary of the person that wants to hire me – and the salary of the last person to do the job, and the salaries of those I’ll be working with.

      Imagine that. The salary question is bogus and is intended for one thing only: To put a cap on any job offer they give you. So think like the business person you are, use your good sense, and say NO.

  43. My experience about getting “extra paycheck hours” as an entrepeneuse is your success to hide depends on: how you present your self employed attitude, what you have been doing in its venues, if the regular time clock job is in ally to your past job and\or self employed venues. You can’t be too self sufficient minded or ego about it because that would ace you out. I try to come off as both a pay clock employee and self starting, creative, resourceful entrepreneur. I work effectively alone as much as in a team, and I am a very willing team player.

  44. The majority of my work experience is self employment. Ive built a multimillion dollar operation, and have achieved incredible things in my own, but I suspect that has made me completely unemployable. I’ve been looking for employment for 5 years now. I haven’t even landed a phone interview in 4 years. Good luck.

  45. It’s not got anything to do with what I’ve been told, it’s experience. My experiences are very similar to Derek.

    If you’re self employed and have run a business for a long time (10 years), you’re completely unemployable and it’s precisely because businesses don’t want to employ you and not because you won’t be able to adapt to working for someone else. After all, when you run a consultancy you constantly work for other people and are repeatedly told what to do by your clients. It’s an utter fallacy that you’re your own boss. Once again, I know this from experience.

    Most self-employed people as a minimum have business development, account management, project management and business admin experience. Sometimes it’s a lot more. Doesn’t make a blind bit of difference to recruiters and employers though.

    As a self-employed person, you’ll likely have far more experience than a junior or mid level employee in the corporate world and this bizarrely makes you a very a hard sell because you don’t neatly fit into a box and will very likely have more experience than the person hiring. Many hiring managers are intimidated by this.

    Recruiters only look at your CV for 6 or so seconds and most won’t touch a self employed person with a barge-pole because they’re not easy to sell to their clients. Why put effort into trying to sell someone when a candidate with conventional experience who fits neatly into a box comes along? Thus, it’s the path of least resistance for commission.

    People should always remember that recruiters aren’t out to help you, they’re simply after a quick sale to meet their on target earnings and will always disappear without a trace if you’re of no use to them.

    HR professionals are just as lazy but for different reasons and often can’t be bothered to read between the lines with regards to a CV because they’re inundated with CVs all the time. Being self-employed is just another excuse to filter you out of the sift.

    If you’re self-employed looking to make the transition back into working as a PAYE employee, you’ll be looking and applying for jobs for a very long time until you have success. Very few employers are willing to take the risk on a self-employed person.

    Why do I say this?

    I’m Master’s Degree educated and have run a successful internet based business for nearly 9 years. I’ve 16 extremely glowing client recommendations/testimonials on LinkedIn and as you can imagine, I’ve transferable project management, account management and business developments skills. My business is still profitable although I’m admittedly a one-man band.

    However, I’ve lost all passion for the job and want my life back as I even had to take work away with me on my honeymoon. I’m thus seriously considering my options.

    As a result of the above, I’ve applied for over 200 Account Management, Project Management and Business Development jobs in the last 4 months. I felt they were all jobs I could easily do and I ticked all the boxes with regards to the experience and skills they wanted. I’ve applied directly and through recruiters and took time to tailor all my applications. Yet, I’ve not had a single phone call or personal acknowledgement by email (apart from automated rejections).

    You’d think someone who’s intelligent, diligent, self-motivated, entrepreneurial etc would be in demand with recruiters and employers. Not the case at all. Employers want obedient workers who do as they’re told…even in sales.

    I know I’m unemployable and I know the only way I’ll get a job is if I’m dishonest and downplay my experience and qualifications to an almost ridiculous level. I think it could take me at least 2 years to get out of my business and the thought of that makes me very miserable.

    • James B is 100% correct. I’ve done the same things he has, and thousands of job applications later, I’m still unemployed. I’ve recently begun pushing hard again, thinking that since we are at nearly full employment, someone might give me a chance. Unfortunately, nothing is happening. After many months of doing nothing but applying to jobs for 8 to 10 hours/ day, I’m about to give up.

      Self. Employment. Is. Permanent.