When an Entrepreneur Quits and Has to Find a Job

April 28th, 2015

Being a entrepreneur is hard.

Even though I wrote a book about alternatives to a job (51 Alternatives to a Real Job), and I talk about multiple streams of income, and I regularly present to youth and adults about starting their own business, and I think that being creators trumps being consumers any day, I know that being an entrepreneur is hard.

It’s not for everyone.

And at times, it’s not for anyone.

In a recent email from a JibberJobber user, I read: “One of the discoveries I made is that I am an entrepreneur at heart, but not at the moment.”

Not at the moment.  Sometimes the timing is right, but that doesn’t mean the timing is always right.

A few months ago a close friend who has owned a software business for years closed shop and got a “real job.”  The emotions in this type of transition has to include:

Elation beyond measure, to get a regular paycheck (no more high ups and low downs).

Sadness, because of having  to move on from having built something that is just not buildable anymore.

Embarrassment and shame to quit on your dreams of so many years, and admit that you simply weren’t good enough to make it work.

But circumstances shift, needs change, support from family changes, markets evolve. At the intersection where dreams meets reality, you learn just how hard it is to get something close to break even, much less highly profitable.

Your respect for those who founded and created businesses from yesteryear skyrockets as you realize that to get to what looks like an easy, privileged and exotic lifestyle, founders had to sacrifice health, relationships, and sanity.

I’ve seen this over and over.

I’ve seen entrepreneurs-at-heart pull the plug on their dreams and get a job.

And here’s what I think: THAT IS OKAY.

I read Seth Godin’s book, The Dip, and what I got out of it was you have to learn when to quit or change course.  He’s not talking about quitting in a depression and giving up on life.  He’s talking about figuring out when to change what you are doing, either in a big way (close your business) or a small way (change your strategy, offering, packaging, etc.).  Change, re-evaluating, and some-might-call-it-failure, is OKAY.  It’s necessary. It’s expected.  It’s important.

You’ve heard that you should fail quickly, learn from it, and move on, right?

This is a really, really hard pill to swallow when it’s your idea, your business, your attempt.  It’s your ego, and eventually, your identity.

Quitting means you don’t believe in yourself.  You slip into a depression where you have validated, once again, that you weren’t as competent and qualified as you thought you were.  Perhaps you will only amount to being a cog in someone else’s wheel.  This is not the career you envisioned.

But in reality, you shouldn’t think that way.  Whether you are a cog in someone else’s wheel, or you create the next Facebook, you have value.  And as I mentioned earlier, circumstances change.  Maybe your role as cog today will lead you to successful entrepreneur in the future.  Or maybe you’ll be a great cog, with a great career, with financial stability and all the joys that can come from having a fulfilled life.

I admit that I have always wanted to be an entrepreneur, but I couldn’t figure it out until the idea for JibberJobber came.  There were a few false starts with other businesses, but my heart wasn’t in it, and they weren’t the right path.  I eventually pulled the plug on them.  But when JibberJobber came, it was like a calling from God.  And for parts of the last nine years, that calling has been hard to fulfill.  I’ve done the stuff I’d heard about from other entrepreneurs: lived off of credit cards, borrowed ridiculous amounts of money from family, burned through my 401k, payed my employees for months without taking any salary, etc.

Glamorous?  Only in the movies.

Hard?  Indescribably hard.

Did I think about giving up?  Many times.

Did I have any way out?  I’ve had job offers and buyout offers over the years, but none of them were right.

For now, this is my calling.  I’m blessed to have a wife who is all-in, and gets the vision of what I’m doing. Not to say that there haven’t been times when she wanted something different (like a paycheck every other week), but she gets it.  She supports it.  And that’s the reason why I can still be here, as an entrepreneur, fighting the fight, while I might otherwise get a high-paying job with benefits and vacation, and some facade of security.

Luckily we figured out the money part of this business, which is something that my ex-competitors can’t say.

I choose to fight this bloody, messy fight.

Getting a job?  Pulling the plug on entrepreneurship?  If it’s right, right now, then do it.

I think that’s only a step in the big journey of being an entrepreneur.  After all, with the state of job security being what it is now, aren’t’ we all taking entrepreneurial risks?



Laura Labovich: The How-To Guide for Meeting Your Career-Focused New Year’s Resolutions, KASH and using JibberJobber

January 20th, 2014

laura_labovich_headshot_2I met Laura Labovich at various career conferences over the years.  She is really outstanding.  She is a giver, passionate, knowledgeable, and the type of person who makes you feel good about yourself.

She recently wrote a great article on LinkedIn’s blog titled The How-To Guide for Meeting Your Career-Focused New Year’s Resolutions.  I hadn’t heard of the KASH acronym before, but it stands for knowledge, attitude, skills, and habits.  In the blog post she talks about how to continuously improve each of them.

Of course, I loved the last part where she says (and then expands on):

To improve your Habits, resolve to get organized (thereby killing two resolutions with one stone!)

She talks about tracking various job search activities… and of course JibberJobber is the tool to do that.

Go read her blog post, and then resolve to improve your KASH, and get organized with JibberJobber (thereby killing two resolutions :p)!

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Four more weeks until Jan 2. What are you doing to prepare?

December 2nd, 2013

I’ve run JibberJobber since 2006 and have found that January through March or April is the time when most people are (finally!) really serious about their own career management.

December feels like a month when you can’t really do anything… people complain that it’s a horrible month for the job search.  Employees are out of the office, on vacation, and hiring decisions are left until the new year… so why try?

When I was in my job search I didn’t care what holiday it might have been, or whether it was a weekend or 3 am.  I had anxiety, and I felt a great sense of urgency to do something to end my unemployment!  I wasn’t doing the right things, but I certainly wasn’t going to celebrate anything (like a national holiday) simply because everyone else was.  It’s hard to feel festive when you feel like an incompetent.

What’s more, many job search coaches say the holidays are definitely a time to do job search stuff, even if you employ different tactics.  But let’s say you doing believe any of that stuff… what COULD/SHOULD you do between now and January 2nd?

Whether in a job search or not, smart, astute, “self-driven” professionals are going do something.  It might be as baby-step simple as listing 10 – 20 people they need to talk to, or 10 – 20 companies they want to network into come January.

It might be something as in-depth and time-consuming as writing a book (even if it is a small ebook) with the purpose of establishing and enhancing their personal brand.

That “something might be seriously considering, or starting, a side business, to create an alternative/multiple revenue stream and maybe even start down the path of 100% self-employment.

Depending on what your year (or last quarter) looked like, you might simply take this month off to do “nothing” – like read some books or articles you’ve been meaning to catch up on, take a real vacation and mentally, spiritually and physically recharge, to be ready for the next year.

Whatever you do, please don’t give up on December.  Whether it is a strategic and very tactical job search to hopefully get some interviews or offers lined up in January, or a more long-term career management strategy, take the time to do something on purpose to finish out this year.

I can’t tell you what it should be – so you tell me… what will it be?



Never again say: “I lost my job.” Instead, say this:

November 25th, 2013

A few years ago I was inspired to write a post suggesting we don’t talk about or refer to “job security.”  The idea was that there is no such thing as job security… of course.  I proposed that we replace the phrase with INCOME security.  That is, I am working on securing my income, which might come from multiple sources (not a single employer), might come sporadically (when I make a sale, or through quarterly royalties, or monthly rent payments, etc.).

Doesn’t that make sense?  Shouldn’t we be working towards securing our INCOME, instead of chasing the 1900’s romantic idea of JOB security?

I thought it was brilliant, and wished I could come up with more of those ideas.

Last week I did.  I was thinking of a friend of mine who lost his job as a programmer.  My wife was concerned for him and his family (the sting of our unemployment can come right back when a loved-one starts their journey) but I told her I wasn’t worried about him at all.  As a programmer of some hot languages, I was sure his job search would be very quick and easy.  And it was.  He has since landed and really has nothing to worry about.

As I was thinking about him, and his very short journey, I was thinking about the scariness, and stigma, of being unemployed. Or, of losing your job.  Especially now, with the holidays near, where we’ll “have to” spend time with family and loved ones, and we all talk about what’s going on in our life… no one wants to be that one person who is unemployed.  The token loser.  Something must be wrong with you.  Right?  I know how it feels.  I was there, for many months.

I was thinking, what if we go away from those stigmas (and assumptions) of “I lost my job,” and shift the mindset (or, have a “paradigm shift”)?  What phrase would change the meaning and take away the sting?  I came up with this:

“My contract ended.”

Think about it… a lot of people have contracts that end.  And when the contract ends, you move on to the next contract.  It’s not a horrible surprise (contracts are meant to end, whereas in some fantasy universe we tend to think that jobs aren’t supposed to end).  Okay, sometimes the contract ends early, but not contractor believes their contracts will end when they are ready to retire.

Contractors should always prepare for the ending.  They do this with:

  • fiscal responsibility (spend less than you make, save money for the bouts between contracts, etc.)
  • filling the pipeline (networking, putting bids out, etc.)
  • marketing themselves (know how to talk about your products/services, know when to talk about them, know who you want to talk to about them, etc.)

An employed person, though, who fears losing their job, doesn’t do these things the same way a contractor does.  The employed person fears losing, the contractor prepares for the loss.

This phrase, when said out loud, changes the course of the conversation.  Instead of “oh, you poor person who must have caused too much friction at work!”, it is more of a “Oh, sorry to hear that, what’s your next contract?”


This phrase, when you INTERNALIZE it, empowers you to be more in control of your career.  You really do become the CEO of Me, Inc.  You are no longer a victim of a bad boss, of HR, of the market, etc.  You are empowered to prepare for the end of the contract.

Isn’t this awesome?

Many years ago I started working at a janitorial firm.  In the first month or so of that job we lost a $5M contract.  I went to work the next day a little nervous, wondering what kinds of cuts they might make at the corporate office.  The CFO seemed happier than usual, and I somehow remember him whistling in the hallways as he went about his duties.  Later I asked him to explain how they could lose such a big contract and still be happy, or not be overly worried.

He replied that the company had been in business for a long time, and that they had won and lost many contracts.  It was no big deal, and there would be more contracts they would win.  And in fact, they did win many more, and the company grew a lot while I was there.

That mentality is the same mentality that we, as CEO of Me, Inc., need to have.

What do you think?




Pamela Slim and Merideth Mehlberg: Test Often and Fail Fast (free webinar)

February 26th, 2013

I’ve known Pamela Slim for years.  She’s the creator of Escape from Cubicle Nation.  Anything she does is awesome.

She’ll join Merideth Mehlberg tomorrow at 12:15 PACIFIC time to talk about starting a business.  The entire title is:

Test Often and Fail Fast: The Art of Rapid Deployment to Quickstart Your Business.

Here’s the link to join the webinar. Merideth has a really cool program called The Career Gold Club, which she has interviewed me for.  Definitely worth your time to check out.

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What Does Emergency Gall Bladder Surgery Cost (aka: health costs when unemployed or self insured or as an entrepreneur)

February 16th, 2013

A month ago, at this very minute (note: I started this post on Friday but took a very rare sick day during the post), I was laying in a hospital bed trying to “breathe through my nose.”   I never disliked breathing more than that day.

You can read the entire story here (I need to clean it up because I wrote it when I was on narcotics… it doesn’t read as well as it should).

The purpose of this post is to talk honestly about what you can expect to pay if you have an emergency that requires you to go to the E.R.

There were five or six vendors or service providers involved in this.  Below is what I was billed (approximations):

Hospital, including emergency room, operating room, recovery room: About $18,000

Operating surgeon: about $1,600

ER doctor: Bill amount: $888

Pathologist: To do what, I have no idea. Bill amount: $49

Anesthesiologist: Bill amount: $1,275.

Radiologist 1: Bill amount: $119.86.

Radiologist 2: Not sure if there was one, but was told there might be one.

Each of those are independent from one another, and no one would tell us what the bill might be, or even who to contact.  It was either make calls and figure it out or wait for the bill to come.

There is a reason to make the calls immediately.  Many medical vendors provide a discount for “self-pay,” which is the term you use if you don’t have insurance.

Why we don’t have insurance is for another post.  Trust me, we tried to get it (more than once), but the insurance industry is so corrupt it is disgusting.

Anyway, if you are self-pay there are two things that happen:

  1. 1. You get offered a discount – up to 50% off.  You can see the discount amounts below.
  2. 2. No one believes you will pay.  The government and media has done a masterful job creating an image of uninsured people (aka, self-pay) that if you are self-pay people think you are going to not pay.  Not true, but thanks to the gov’t and media, that’s a new stereotype to live under.

Here are the discounts we got:

Hospital, including emergency room, operating room, recovery room: About $18,000. They gave 50% off to self-pay if you pay within about 2 weeks.  That meant our bill would be about $9k.  We went in to talk about it, and when to pay, and the finance person lowered it another $1k (because much of the time billed was when I was in “recovery,” which didn’t really take the same resources as a bunch of people doding on me every minute.  Total bill: a little shy of $8k (for about 55% discount).

Operating surgeon: about $1,600. When I went in for the post-op checkup they said they would offer a 50% discount if paid THAT DAY or a 30% discount within (I don’t remember how many weeks).  We paid that day. I wish they could have given a little flexibility – perhaps 50% if paid in a week.  It wasn’t fun to pay that day, considering the payment to the hospital was made in the same week. Total bill: I think it was almost $800. Are you blown away that the person who controls the operation gets only $800 (less whatever his company takes in overhead)?  Crazy.

ER doctor: $888. I found their information and called them and learned they offer a 50% discount. I have to pay that by early March, which is about a 6 week timeframe.  Very thankful for this discount and the extra time. Total bill: $444. Nice savings :)

Pathologist: To do what, I have no idea. Bill amount: $49. They offered a 30% discount, which we were thankful for.  Ended up paying $34.

Anesthesiologist: Bill amount$1,275. I was highly disappointed in their discount, only 20%, to bring it down to about $1,000.

Radiologist 1: $119.86. 20% off put it down to (total bill) $95.89.  Not liking the small discount but the amount was so small that it was sixes.

Radiologist 2: Not sure if there was one, but was told there might be one.

The total out of pocket for this emergency surgery was about $10,375.

Are you ready for that capital outlay right now?

I wasn’t either.

Aside from being on insurance, what can you do to get ready?  I’m not talking about preventative because this could have been an ambulance ride from a car accident (and healthy eating usually doesn’t prevent that).

If you got a $10,000+ bill from the hospital, would you be in a world of (financial) pain?

You can prepare for medical emergencies.  I recommend:

1. Regular insurance

2. Accident insurance

3. Robust and growing savings

4. Knowing who you can tap into to get help from (family, etc.)

It’s a scary time without this $10k bill, but being able to do it can come from planning and preparation.  Start NOW!



The REAL Unemployment Rate (it is not what the news tells you)

October 12th, 2012

I hate reports of the unemployment rate.  They are lies, usually.

Check out this post from Bill Humbert on to understand the unemployment rate.

Check out my commentary on it at Career-Resumes.

Here’s a visual… Bill says the government reports an unemployment rate that is just part of the picture (U3).  The real unemployment rate, he says, is a few lines down (U6). (click image for original source)

Of course, the reality is if you are unemployed, your PERSONAL unemployment rate is 100%.

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Job Search News: What’s Up

April 13th, 2012

The economy seems to be getting better… at least, when I speak, the job clubs say they are having people not come back because they land.  I’m hearing this a lot, lately.  That’s great, right?

In other news, layoffs are still abundant. Yahoo just dumped 2,000 engineers into the Silicon Valley area (again). Sony dumped 10,000 people (not sure where they are, I’m guessing many of them are outside of the U.S), and the Detroit Public School system pink-slipped “at least 4,100teachers.

No one is safe from this.  Nowhere is safe.  No industry is safe.  What used to be safe (teacher, gov’t employee, etc.) is now fair game.

What does this mean for you?

Prepare on your own with the right skills and credentials.  In the olden days (a few years ago) that meant a good, solid education.

I think today it means something else (not necessarily replacing education).  Here are three things YOU can do to protect yourself, and try and get some sense of what we used to call “job security”:

  • Sales ability. When I got laid off my younger brother said to get a sales job for one to three years, just to get sales training and experience. I think this is brilliant advice.  We sell all the time, but we aren’t trained, and we aren’t fearless, and many times we do a bad job.  Whether you think you are a “salesperson” or not, start learning sales techniques and strategies.
  • Entrepreneurship. Decades ago you were a cog in a wheel.  You had a place, and depended on all the other cogs to do their job, and things would work.  You let higher-ups make the strategic decisions that would affect your livelihood and future spending capability.  TODAY it is different.  This year you might have multiple jobs, or multiple income streams.  That’s not bad. Personally, I think it’s empowering!  It’s awesome.  But we need to have that mindset change so we understand that we need to do our career more intentionally, rather than just “show up.”
  • Career Management. For me this means cultivating and nurturing your network and your brand.  No one else is going to do this.  It’s up to you to finally get serious about your relationships, and how you manage them long-term, as well as how others perceive you (aka, your brand).  Keep neglecting this and your degrees and experience will sit on the shelf getting dusty while you have long, painful job searches.

What have I been up to?

I’m cranking through my book 101 Alternatives to a Real Job.  I hope to have it done and shipping by July, when I head to the D.C. area for some presentations.  If it’s out in July, it will only be 7 months behind schedule :p

What have YOU been up to?



I wonder if the election will make employers cautious about hiring? #bad_news?

January 25th, 2012

On the user webinar this morning someone asked my thoughts about their situation: two advanced degrees, and not even able to get an entry level job.

I have a few thoughts on that:

The idea of a career and job has changed.

I’ve blogged about this quite a bit.  No longer are we shooting for a long-term career with retirement benefits.  We’re happy if we find a place where we might settle in for a few years.

My recruiter friend Robert Merrill told me a couple of years ago that he thinks we’re getting closer to becoming a world of 1099 workers.  What’s that?  1099 workers are contractors.   No more FTE (full time employees).

Have you seen a trend moving in that direction?

Even if you are hired as a FTE, the company treats you as a 1099, with frequent layoffs and rehiring.  Crazy stuff.

That’s one reason why I’m writing the book 101 Alternatives to a Real Job.

Whether we are out of the recession or not, employers are going to be cautious/skeptical.

Until they feel really good about their market and customers, they aren’t going to commit to the salary and overhead of a new employee, unless it’s critical. (So, how do you prove you are critical?)

The pending election will probably make employers wait on big (hiring, strategy, product line, etc.) decisions.

What impact would Romney or Gingrich have on our economy, trade, markets, taxes, etc.?

What impact would another Obama term have?

Whatever you think it will be, each employer has their own opinion, and they might be waiting on big decisions until… the end of the year :s

Trivia: One of the biggest spikes in JibberJobber signups was when Obama was elected President, through the inauguration.  I was amazed to see how many people started to seriously take career management into their own hands upon hearing that news.

If that’s the case, what does 2012 mean for job seekers?



Surgery without Health Insurance

December 1st, 2011

A couple of years ago we had some expensive hospital work that we were trying to plan for.  For various reasons outside of our control, we didn’t have health insurance.  Today, with a different kind of health insurance we get from employers, and more people out of work, I thought it would be important to bring this up again.

Here’s a post that describes what happened.  It was scary, but such an amazingly positive experience (with regard to the finances). From an August 2009 post:

Three months ago we had a baby and paid for it without health insurance (even cheap health insurance) or government aid.

Last week my wife had a surgery and we’ll have it paid for as soon as we get the final invoice, again without any health insurance or government aid.

You should note that I have NOTHING against private health insurance (well, I think it’s grossly overpriced and doesn’t offer what it should) nor am I against getting government aid when appropriate (more on that tomorrow). This isn’t a political post, or a bashing post… I just wanted to share a couple of ideas that might help you save money (or, be able to afford the health care you need).

When asked what our insurance is we simply respond that we are “self-pay.”  This means it doesn’t go through insurance, rather that we pay for it ourselves.  As self-pay you can finance the service(s) through the service provider (hospital, doctor., etc.).  Or you can pay in full.  Why would you pay in full? Read on.

When we had our baby we told them we were self-pay and asked them if they offered a discount.  Guess what the discount was?

OVER 50%!  Instead of paying more than $8,000, our total hospital bill was around $3,400.  That is a huge, significant savings.  I like getting things on sale, and I like saving almost $4,000.

Note: We had to pay this in full before my wife got out of the hospital.

Fast forward three month (yeah, surgery three months later sucks).  My wife goes in for a surgery, fairly standard, and the doctor said he would do surgery wherever we wanted, so we could shop around.  We didn’t know you could or should shop around, asking hospitals what the cost would be.  We found there were pretty significant differences and chose to stay with this same hospital, which offered 50% off of this procedure. (we also learned that if you are insured and pay the copay up front you save 25%)

The doctor also offered 50% off – we took advantage of this for both the birth and the surgery.

Did you know you could save so much?  We had no idea.  But for us it’s a necessity.

We also learned we could get a prescription for any oral medicine the doctor would prescribe that was to be administered in the hospital and get that filled at our local pharmacy and then just bring that in for another significant savings.  I have no idea how much we saved but it was cool to know we could do that.

My point with this post is that health insurance isn’t the only way to get stuff paid for… if you don’t have it simply ask your doctor or the staff (the medicine thing was a suggestion from his front desk staff), and the hospital finance people… there are plenty of people who are self-pay and it isn’t as bad, scary or undoable as we thought it would be.

The scary part of this is that it exposes how expensive health insurance is.  If a doctor and a hospital are willing to discount 50% of their invoice just to (a) get paid in full upfront, and (b) not go through the insurance system, can you imagine what healthcare would be without health insurance in our system?

Do you have any other suggestions on finding affordable healthcare.

Two years later the question is still highly relevant – what suggestions do you have?

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