Many small businesses fail when their owner has to take an extended leave due to health concerns. Your ability to handle stress is significantly reduced when your body has been neglected for a long period of time. Also, whether you want to believe it or not, there is plenty of science to show a healthy body and healthy mind go hand in hand.

So, if you want to get the most out of your business, handle stress better, and keep your mind sharp, it is your JOB to take care of yourself.

I should probably go back to my Part 7 post and add “I will take care of my body every day no matter how much it sucks” to my list of 20 things.

The first argument that always comes up when I say this is, “I don’t have time to workout.”  You have to MAKE the time. Just like it’s critical to always make time for your family when you are working, it’s critical you make time to take care of your health as well. That hour you spend in front of the TV could have been spent going for a good walk/job/run. That time you spent surfing the internet when you got home? You could also try going to bed earlier and waking up extra early with a great workout.

You have kids? Great! That provides dozens of ways to work out, not obstacles. If you own a business, it’s a part of your life just like your family, friends, and community. You have to make adjustments to the reality of what that means.

Married, engaged, boyfriend/girlfriend who deserves a big chunk of you time? Perfect! You now have a full time workout buddy. One of the best bonding experiences you can have is having a really fun workout together. Ride bikes together, jog together, entire a half marathon together, roller blade, join a team sport like a volleyball league, etc… The ideas are endless and the options can be really fun.

Single, no kids? Then you really have no excuses to not take care of yourself. Seriously. My partner and I worked 16-18 hour days in the first year of our company and we both still found time to work out 5 days a week. As I said you have to MAKE the time, no matter what.

Another one I hear is, “But I don’t have a gym membership” or “I can’t afford a gym.” Who made it a rule you have to go to a gym to workout? As I have already listed above, there are so many fun and free ways to go get some good ole fashioned exercise.

You just have to make it a part of your daily routine. No excuses, it has to become second nature.

For me personally I wake up at 7am and workout for 45 mins. Typically cardio. Quick shower and off to work. Then after work (that varies from 7pm -10pm) I typically walk around downtown a little while. It provides a good bit of time to relax, get some more exercise in, and allows me to clear my mind. That’s what works for me and my lifestyle, obviously that’s not possible for everyone.

A couple times during the course of the 6 years we have hit some pretty significant money problems. Moments where neither Lev nor I was sure the company could last another month. One time it was something we saw coming and we had time to prepare and the other we were caught completely off-guard. Both experiences were very different and required their own unique solution.

Based on that, plus a few stories I have heard from some of my friends, here are some tips on trying to survive a financial meltdown.

First off and most importantly, are you out of money because your business model is flawed and/or your management is terrible or are you out of money because of an unforeseen problem or something outside your control?

If your business model is failing, honestly it might be a good time to consider getting out while you still can. The combination of no cash on hand and a failing business model is the final nail in the coffin. Knowing when to walk away is one of the traits of any good entrepreneur.

If you are financially devastated by something outside your control or unforeseen (a lawsuit, a credit line cut in half, your biggest customer decides to cut back on spending, a fire, flood, etc…) then you do have a lot of options, but it’s very important you understand the financial and emotional risk you are taking on.

You have decided to push onward and try to get your bank account back on track. There are a lot of ways to perform financial CPR on a dying company.

Do you actually need a loan or credit line or do you just need to do some creative bill balancing? Take a hard look at your cash flow, who owes you money, and who you have to pay in the short term.

• Is there a creditor you can negotiate a late payment with? If they are an unsecured creditor, are you willing to default on the debt?
• Is there an accounts payable you know you can ask for a delayed payment to and buy yourself some more time?
• Try to negotiate seller financing with all the people you owe money. You would be surprised to discover that when faced with getting $0 or working out a payment plan with you, a lot of your accounts payable will work out a plan.
• If you have employees, are they willing to take a pay cut or go a month without salary? (This includes you by the way.) If they are unwilling, can you operate with a smaller staff?

If you decide you do need financing there are a lot of options for that route as well:

• Traditional – In this economy, what is traditional financing anymore? Walking into a bank and getting a small business loan has become as difficult as getting into Harvard. You probably have a better chance of getting run over in the crosswalk outside the bank and getting $200,000 from the driver, then stepping into the bank and trying to get it from them.
• Sell something – Do you have a non-core asset that you can part with? It may be painful, but if all you need is 30 days of operating cash and you feel you will be right back on your feet again, consider which company assets you could sell off for quick cash.
• Your Home or Cars – Use the existing collateral you have to secure a loan for the company. Do you have any equity you can pull out of your home? Keep in mind in this economy it’s become harder to secure large second mortgages or mortgage refinance loans. So, this option isn’t nearly as useful as it used to be. Also, if the business goes under and you can’t pay your mortgage anymore, now your homeless.
• Credit Cards – Many a small business has been launched and saved by the good ole credit card. One advantage is the debt is unsecured so you won’t lose any assets, the bad news is the debt tends to be high interest and most likely we are only talking about maybe $10-20,000 in credit anyway. So, this isn’t going to be a good source for a large loan, but it might be suitable for you.
• SBA Loans – Maybe you qualify for a SBA loan. Check out their site and find your local SBA branch http://www.sba.gov/localresources/index.html
• ARF – If you have a large volume of accounts receivables, you may consider an Accounts Receivable Financing company. I consider this to be pretty low on the list of options since the interest rates and fees tend to be really high. Consider it a pay-day loan for a business because that’s basically what it is.
• Family and Friends – Now this may actually be the easiest of all the options to secure, but by far the dangerous to your long term happiness. Taking money from loved ones is going to increase your anxiety and it could be turn into a huge debacle with not only the risk of losing their money (which could be their life savings), but now whether you like it or not, you have brought your family into your business. They aren’t going to behave like a bank. They are going to call or email you every few days to ask about their money. They are going to ask about your plans, throw advice at you, and really start to treat you like a business partner. If that’s something you aren’t comfortable with, then don’t take their money!
• VC – Venture capital companies love to pour money into growing and successful start-ups. However, they don’t like to put money into failing ones. If your revenue has been going down for a while and your growth is non-existent, it’s highly unlikely that you will be able to secure VC funding in this economy. Also, the process of doing due diligence can take months, which means you may be out of business before you have a chance to get money from them.
• Angel Investors – There really are wealthy people sitting out there looking to put there money into start-up companies. These are typically just individuals or a small group of successful business people who get a thrill out of investing in small companies, struggling companies, etc… The downside is it can be very difficult to find one, let alone actually get their attention. If you do however, they tend to move a lot faster than a VC company.
• Mafia – Are you connected? Just kidding. But, seriously are you connected? Then you know what to do to those accounts receivable. Make them an offer they can’t refuse.

Hopefully that helps you get some ideas flowing about what to do when the money runs out. When money is tight is the time you need to step up and be as creative as possible. It’s really one of those moments where you either rise to the occasion or get out.

I can remember when we first started off back in 2004, we were completely focused on building insurance websites. There were no distractions, no big dreams just yet, just good websites delivering a rather simple, but profitable service to our customers.

One day though in the spring of 2005 I heard a song I really liked on the radio, Googled her name, saw she didn’t have an official website yet, so I decided “What the heck, I’m a web designer, I’ll build a little fan page for her.”

What started off as nothing more then a fun personal project, ended up turning into a giant waste of time. The worst thing that could possibly happen ended up coming true: the web site was a big hit. Within 3 weeks of launching my little fan page the site was getting over 2,000 visitors a day.

The website actually climbed all the way to the #1 spot on Google for her name do to my SEO optimization and people started to think it was actually her official website. The traffic exploded when this person’s song ended up climbing all the way to the #1 spot on the Billboard Hot 100. The site was now getting close to 15,000 visitors a day.

I was running Google AdSense on the site, which allowed me to earn revenue for every time someone clicked on one of the ads being displayed. By the time the traffic started to peak I was making about $150 a day off the site. When you are 22 yrs old and completely broke, $150 a day feels like a million.

Then I made the first of many mistakes. I thought, “Wow, I bet I could do this over and over again!” Mistake #2 was I told my partner Lev that I bet we could build dozens of these sites and start earning a thousand dollars a day in probably six months of work. Mistake #3 is we both agreed to give it a try.

Next thing you know we are dedicating 25% of our time to building these sites and the rest to our core product of insurance websites. Everything on the insurance end started to back up and slow down because of this, but we were so blinded by the amazing traffic growth in our network, we didn’t notice.

About five months into the project we had hit 1.5 million visitors per month (about 30% of that was my original site by itself). Revenue had climbed, but was a measly $8000 per month. Our server costs had climbed to $900 per month, we had a full time writer to keep all the sites updated, and we were wasting nearly a third of our company time on the music network now.

One day Lev comes to me and says, “We are in this to make money right?” I didn’t really know how to respond, because I had my head down the whole time grinding out these websites and all I saw was the traffic growth. I wasn’t looking at the bottom line.

We took a good long look at the last five months and decided to kill the project. At the end of the day we had become so distracted by growth, we forgot to make money.

My message from all of this is you need to focus on profit from day one. Keep your costs minimal, hire slowly, and focus on making a profit from the first month you are in operation onward. Of course I understand for many businesses it’s impossible to generate a profit for several months just due to the nature of their industry. Also, I realize for a lot of industries like the restaurant business generating a profit is incredibly difficult in the first year, so the focus should be on being cash-flow positive as quickly as possible.

Regardless, the focus needs to be there from the first second you open for business. Growth is fun, large volume of product is great and all, but at the end of the day all that matters is if you are profitable or not. I see companies taking round after round of VC funding and burning through it like it’s toilet paper.

They are fantastic at spending money. You need to be fantastic at generating profit.

What was the end result of switching our focus back to profit instead of growth? We put all of our efforts back into our insurance sites and by the end of 2007 we had approached nearly one million in revenue. By the end of 2008 we did $12 million. 2010 is shaping up to blow all of that out of the water.

Looking back I can’t believe I ever let myself get distracted by growth being the sole factor as a measure how successful the company was.

(This post was the inspiration for my Business ADD post by the way…)

I have seen it with business associates I know and first hand with myself. You taste success and my lord does it taste good… All of a sudden that 65”  HDTV doesn’t seem so unaffordable. All of a sudden your office strikes you as the perfect place to put in a pool table. Company paid getaway for everyone? Sure, why not…

Success can fool anyone into thinking that more success is right around the corner.

Maintaining humility in their start-up years is one consistent theme you will find in nearly every single highly successful company. When you finally start to get a little success under your belt and a little profit in your pocket, understand that your hard work and frugality was what got you there.

So, first off try to keep things in perspective. The old saying “success breeds success” is nice and all, but like my last post talked about, short term results to not predict long term trends. You don’t know how long the good times are going to last, so stay frugal. Give yourself a reasonable reward. Ideally it’s something involving a hobby of yours or something that will help you relax. Success can bring additional stress, like expansion and hiring new employees. So, reward yourself with something fun and something that will help you get away from the stress of work. Maybe it’s buying used SLR camera because you love photography, maybe it’s a round of golf at a nice golf course, maybe it’s a romantic night with your partner. All that matters is you enjoy it and you give yourself a pat on the back.

Secondly, you deserve a reward, but if you have employees, they do as well. You first success can be one of the single best team building moments you will ever have. It’s your first opportunity to show your employees what kind of owner you are going to be when the money starts to flow in. Are you going to be the boss who takes 95% of the profits and buys yourself a new car, or are you going to be the boss that takes everyone out to dinner and gives them all a small bonus?

Every dollar you invest in your good employees in your start-up years will come back 100 fold in the long run. That’s something I can speak for personally.

Third, start saving! I don’t know why this isn’t covered more in business blogs, but saving money is not just for personal finances, companies need to save money as well. I realize in the start-up days all your funds are typically depleted each month, are all going toward marketing, paying down loans, and trying to expand. But you need to place something aside as a rainy day fund. Having cash on hand be an absolute life saver.

Fourth, remember you have to pay taxes on profits. Don’t treat profits like a credit card that you hope you will pay back in time for next April. This goes along with my third point above and is a very common reason why so many businesses end up with tens or hundreds of thousands of dollars in back taxes. You don’t want the I.R.S. chasing you.

Try to keep those four tips in mind and I think you will find when the day comes where you really have “made it”, the big rewards will feel so much sweeter.

The easiest place to find fantasy is in those first months of any new business. When Lev and I started off back in 2004 we continuously made unrealistic expectations one after another. Especially once we tasted our first success, our imaginations ran wild.

The more the confidence builds the more you can start finding yourself making some pretty ridiculous assertions. “I think we can keep up our 3000% growth for at least a couple more years.” “Wow, this month was our best month ever, I bet we are going to just keep exploding like this for the rest of the year!” “Hey, I got an email address finally for one of the contacts over at XYZ company, I bet this is the in we needed and we will be talking to the CEO in no time!”

Keeping realistic expectations and keeping your optimism in check are really critical for a couple reasons.

1. You won’t be crushed when things don’t work out the way you dreamed they would.
2. You won’t waste a whole of bunch time chasing some fantasy that was never achievable in the first place.

I’m not saying be a pessimist and a cynic. There is no place for pessimists in business other than corporate accounting and Economics departments at universities.  Other than that, the business world is a place of optimism.

What I am saying is the next time that adrenaline kicks in and the light bulb goes  off in your head, try your best to make sure you are not reaching for the stars, but a low hanging branch first. Take things slowly; step by step. Set small realistic goals for yourself, your company, your employees, etc… and as you achieve them, give yourself a pat on the back and move on.

To think because you closed one great deal and you did it quickly, that you will be able to do it from now on is silly. I have closed major deals in a matter of days only to have a small deal drag on for weeks of negotiations. The business world is relatively unpredictable in many ways, so trying to build concrete dreams around it is an exercise in futility.

If I could come up with a list of the best ways to avoid leaving optimism and falling into the pit of fantasy, it would be this:

1. Don’t base long-term expectations and hopes on short term results. I have done this many times myself and it’s a really hard habit to break. You had a record month? That’s great; now buckle down and try to match it again the next month.
2. Set realistically optimistic goals on a short time line that you want to hit. Setting really grand goals and putting them on long time lines is a recipe for failure.
3. Be pragmatic. Base your expectations and plans on what you can actually verify or quantify or logically presume. You second cousin’s ex-wife’s dog groomer says he has an amazing business opportunity that can make everyone millions! Where do I sign up?

Leave fantasy where it belongs: the entertainment industry, children’s books, and politics. Business is a place where optimism must exist and it must drive your actions, but where it must always be kept in check and balance with rationality.

I feel like many people really appreciated it and felt a strong connection to the content. However, I also feel that my words were misunderstood  by many readers. So, in order to explain my list a little more I have decided to break each of the 20 down with further explanation:

1. I am willing to lose everything. When I say I am willing to lose everything I mean that in a very relative way. Think of it more as an mental attitude than a literal loss of everything you have. Not everyone is going to approach the thought of losing everything the same way. To some losing everything might mean their house, car, and credit score but still living in an apartment and having the ability to rebuild their life. To some it might mean living on the streets homeless and divorced. To others it might mean losing their life savings, but they still have their house, car, and can support their family regardless. And to some it might simply mean losing that particular business, but nothing else in their life.  For me personally, losing everything takes me all the way down to being homeless. I can’t say that’s a good idea, nor would I suggest anyone to consider that a rational approach to business, but it’s just built into my personality and who I am.
2. I embrace failure. I can’t stress this one enough and I really don’t feel that any list of qualifications for being a entrepreneur should ever exclude this one. You have to fail to succeed. You will learn so much from the mistakes you make as an entrepreneur. The successes are so easy to take for granted and sometimes even ignore as you are too busy growing your business. The failures though hit you right in the gut and force you to re-evaluate what you are doing and more importantly make sure it never happens again.  I have made many mistakes in my business career; some humiliating and some financially devastating. Every time I walked away with a new set of lessons learned that you will never find in a single chapter of a business textbook.
3. I am always willing to do tedious work. What I mean by this one is you have to always be ready to jump back into the trenches. Even if you are taking home $150,000 in salary and you have hired 30 employees, if there is work that must get done and no one around or qualified enough to do it, the entrepreneur is always ready to jump in and do the work no matter how menial or tedious it is. Personally, a while back an employee left unexpectedly and this employee held a rather critical job that no one was really qualified to do except a few people in the company. I stepped up and did the work on top of my normal work even though I must admit it was some of the most boring tedious work I can ever remember doing. I quickly gave the people in that department a raise shortly afterward once I realized just how tiring their work was.
4. I can handle watching my dreams fall apart. When you start your first business it becomes your baby. You build a whole set of dreams, hopes,  and plans for its future in your head. You can see it all playing out just they way you designed it and the uncertainty combined with excitement is just wonderful to be honest. Then like 50% of small businesses, according the Small Business Administration (SBA), the company fails. Watching your dreams melt away either strengthens you or it defeats you. When I say “I can handle watching my dreams fall apart.” I mean in it the sense that a successful entrepreneur can pick themselves up after a failure and march on. You move onto the next idea, you learn from your mistakes, and you don’t let your past company problems destroy your happiness.
5. Even if I am puking my guts out with the flu and my mother passed away last week, there is nothing that will keep me from being ready to work. OK, some people have taken issue to this one, saying that I was being too crass and if someone followed this item they would die young. Yes, I did take a little creative license with my wording to spice the post up a little. Maybe the mother passing away part was a little crass and to anyone who thinks so, sorry about that one. The truth of the matter is when you run a small business, especially in the very early periods of it, YOU are the business. When you are sick and out of the office, the company does not function anywhere near as well as it should. When money is tight and every single sale, customer, or contract is absolutely critical and you have deadlines looming, there is no such thing as a sick day.
6. My relationship/marriage is so strong, nothing work related could ever damage it. Does this one really need any further explanation? If you love your quality of life, love your ability to be able to spend weekends and nights free with your family, like getting a steady paycheck and having the emotional security that it brings for you and your partner, then you should probably think long and hard about how much starting a business can change that. Also, if your marriage or relationship is already having issues and you really want to make sure it improves or you can repair it, then bringing even more stress and limits on your personal time is pretty much a terrible idea.
7. My family doesn’t need an income. Having a family and then starting a business brings all sorts of new challenges into the equation. For many lucky entrepreneurs, including myself, we started our companies at a young age or during a period of time without kids or anyone to support. For everyone else you really have to take a step back and look at your finances, potential revenue, expenses, etc… and do some pretty darn important math. “If my business doesn’t generate enough revenue by X date, there is a very good chance I will have no money to support my family.” This is a very real concern that should not be taken lightly no matter how good your business idea is or how many potential clients you have lined up, you never know how much its going to generate or cost until you start.
8. This is a connected world and I don’t need alone time. I want to be reachable 24/7 by my employees, customers, and business partners. The internet, cell phones, email, text messages, and voicemail are all wonderful but the downside is you are always connected now.  Employees for the most part get to go home, relax, separate their work lives from their personal, and for the most part be unreachable if they want to be. However, when you are the boss it’s the other way around and that employee is calling in sick at 9:30pm the night before they are supposed to deliver a critical proposal that you now have to cover for them. Or when a customer calls panicking while you are sitting at your son’s baseball game because the garage door you installed has crushed their new convertible. Or your business partner calls during Sunday night’s family dinner to let you know there was an accounting glitch and you lost $10k that month, not profited $10k. Since it’s your small business and your partners, customers, and employees are the lifeblood, you are now connected to them at all times.
9. I like instability and I live for uncertainty. Owning your own business means a lot of not knowing. You plan the best you can, you put in the long hours, you do your research, and build the best product or service you can, but at the end of the day, you never really know how it’s going to work out until you start the daily grind. These leaves a lot of uncertainty and instability in your life. You’re not going to be able to count on paychecks each month or which weekends you are going to have free anymore. The phrases, “we will see” or “I’ll let you know” become a very common part of your vocabulary when talking to family and friends.
10. I don’t need a vacation for years at a time. I want to stress that this isn’t forever. I’m simply stating that when you start a business it’s pretty darn likely that you are going to be working. A lot. For a long time. It could be a year at a time, maybe two years, for some people I know know it took three years for them to finally get some decent vacation time away from work. If you are wondering about your vacation time when you are starting a business, you really aren’t asking the right questions.
11. I accept that not everyone likes my ideas and that it’s quite likely that many of my ideas are garbage. If you think that every idea you come up with or try is going to be a success and that everyone is going to want to buy it product or service, you are in for a really rude awakening. Great ideas are great because they come along rarely and they make a real change. Even a good idea is going to be few and far between. So, if you honestly think you are coming up with a great new idea or product every day or week, there is just no way that’s possible.
12. If I go into business with friends or family, I am OK with losing that relationship forever if things end badly. This has probably been beaten to death, but seriously, think long and hard about going into business with a close friend or family member. There is a reason you hear so many people saying don’t go into business with family or friends. You are risking one of your best relationships in the process.
13. I don’t have existing anxiety issues and I handle stress with ease. This one was a personal one for me. Maybe this doesn’t apply to a lot of the people reading this, but I entered the business world with pre-existing anxiety issues. I was terrible at managing my stress and running a small business just amplified that by 100 times. You really need to manage your stress and have a good safe and smart way of dealing with your anxiety on a daily basis. You don’t want to start having anxiety attacks in the middle of dinner where your hands start shaking so bad you can’t eat and you feel like you are having a heart attack. Deal with your stress early and take it seriously.
14. I am willing to fire or layoff anyone no matter what how good of a friend they are, if they are my own sibling, if they just had a baby, if they have worked with me for 20 years, if their spouse also just lost their job, if I know they might end up homeless, if they have cancer but no outside medical insurance, or any other horrible scenario millions of bosses and HR people have faced countless times. Well, this is a sad one but so true. If your company is around for a couple years and you have hired 5 – 10 people, then you probably know exactly what I am talking about here. I remember having to let someone go where I had to leave the office for 15 mins to choke back the tears because I knew I was putting this person in a really bad position by firing them. It’s part of business and on a long enough time-line we all have to do it.
15. I am OK with being socially cut-off and walking away from my friends when work beckons. Just like I said in some of the posts above, owning your own business can really cut into your fun time and can cut you off from your friends. All of a sudden drinks with your buddies after work, going shopping together, and that annual trip you all take to wherever actually has a question mark after it for the first time in your life.
16. I love naysayers and I won’t explode or give-up when a family member, friend, customer, business associate, partner, or anyone for that matter tells me my idea, product, or service is a terrible idea, a waste of time, will never work, or that I must be a moron. At some point in your business life you are going to be questioned. Whether it be someone questioning your product, your business plan, or even your integrity, it’s going to happen sooner or later. It’s how you react to those moments that make you a successful entrepreneur or not. If every entrepreneur quit after someone told them their product was worthless, nothing would ever get built. It’s just the nature of opinions, everyone has one, and a lot of time they aren’t the same as yours.
17. I accept the fact that I can do everything right, can work 70 hours a week for years, can hire all the right people, can arrange amazing business deals, and still lose everything in a flash because of something out of my control. Many people took special offense to this one as if I was being ridiculously pessimistic. 50% of businesses will fail in the first 5 years. Now to assume all 50% of those businesses were all utter failures, terrible ideas, run poorly, etc… is just downright silly. A good percentage of them were probably successful, growing, or amazing ideas. The fact of the matter is you can do everything right and along comes the worst recession since the Great Depression and it annihilates your business at no fault of your own. On the sad end you have many solid businesses fail when the owner falls ill and can’t run it any longer. Or when a customer slips on the front steps, snapping their neck, and takes every last penny you have in a lawsuit. Life happens and maybe this doesn’t belong on the list because it is something that is out of your control, but at the same time, knowing that this happens to other people can be a little something to keep in the back of your mind if it happens to you. That way you don’t think you are the only one that has ever suffered that same fate.
18. I accept that I may hire people that are much better at my job than I am and I will get out of their way. The best thing you can ever do to grow your company is hire amazing employees. But when you see that a certain employee is actually better at doing some duty you consider to be the “boss’s” territory, you need to step aside and let them do it. Maybe you aren’t a very good motivator, so let them give the pep talks or run the sales meetings. Maybe you really aren’t very good at closing deals, so bring someone else with you to close the sale with an important client. Step out of the way of your best employees and crush that ego of yours.
19. I realize and accept that I am wrong ten times more than I am right. This goes along with #11. You can’t always be right. Just because you are the boss and you can crush an employee’s objection or opinion, doesn’t mean a darn thing. Just like #18, the boss is not always right or the best at everything and an employee or customer might honestly have the right answer. Sometimes you really need to get out of your own way.
20. I am willing to walk away if it doesn’t work out. If you can see the end coming, more power to you. So many entrepreneurs, including myself, put up the blinders and charge on even in the face of almost certain failure. It wouldn’t be in the spirit of being a business owner if you didn’t believe in the potential of your business and when information comes along that disputes that, the natural reaction is going to be to ignore it.

Overall my list is designed to help illuminate the potential struggles you may face as an entrepreneur. It is not a checklist of requirements where a Yes to all 20 is required or you shouldn’t even try. Also, anyone who has already become or has found a lot of success being an entrepreneur will say that this list would never have stopped them anyway. That would go against everything an entrepreneur stands for.

Anyone who thinks I am a pessimist really needs to take a second look at that list. It takes pure un-adulterated optimism to launch your first business and to survive the items on this list, it takes even more. Optimism is why the world of small business thrives and why anyone would ever put up with the things listed in my 20.

I find too many business bloggers fail to describe the real experience of starting up a company. They ignore the human aspects. It seems like there is some unwritten law of business blogging that says you can only write about the inspirational and positive aspects of creating a start-up business.

Yes, starting a company can be a wonderful experience. It can be empowering, life altering, etc…….

But what so many business bloggers forget to mention is everything else: stress, anxiety, doubt, heartbreak, sleepless nights, emotional roller coasters, destruction to relationships, lost friends, embarrassment, failed marriages, financial ruin, lawsuits, failing health, creating family rifts, social isolation, unrealized dreams, favors for family and friends, guilt, and the always painful “if” thoughts (“if I just would have ….” “if he just could have ….” “if I had just bought ….” “if the bank just would have ….” “if the customer just …..” etc…. Yes, the wonderful if statements that can haunt you for life.).

I read blog posts like this and I cringe. That idea a simple checklist of idealist generalities can be a qualifier for a potential entrepreneur is leaving a big chunk of questions out.

I answered a definitive yes to 18 questions on the list. But I feel that is missing another 20 questions that are just as important.

Before I go into my list, I want to clearly state that I am 100% for starting a business and chasing your dreams. But I will never imply that is easy or that even a majority of people are good candidates to try it. It can be a nightmare and it can severely alter your life in unpleasant ways.

My list pulls from my personal experiences, but it also pulls heavily from my friends’, family, and associates’ business ventures too.  Hopefully you didn’t think everything I listed above as a negative happened to me alone. I have experienced some of them, but thankfully not all.

In addition to the 20 he asks here, ask yourself if you can answer Yes to this list of statements before deciding whether or not to become an entrepreneur:

(I have written a follow-up post which explains all 20 items in more detail.)

1. I am willing to lose everything.
2. I embrace failure.
3. I am always willing to do tedious work.
4. I can handle watching my dreams fall apart.
5. Even if I am puking my guts out with the flu and my mother passed away last week, there is nothing that will keep me from being ready to work.
6. My relationship/marriage is so strong, nothing work related could ever damage it.
7. My family doesn’t need an income.
8. This is a connected world and I don’t need alone time. I want to be reachable 24/7 by my employees, customers, and business partners.
9. I like instability and I live for uncertainty.
10. I don’t need a vacation for years at a time.
11. I accept that not everyone likes my ideas and that it’s quite likely that many of my ideas are garbage.
12. If I go into business with friends or family, I am OK with losing that relationship forever if things end badly.
13. I don’t have existing anxiety issues and I handle stress with ease.
14. I am willing to fire or layoff anyone no matter what how good of a friend they are, if they are my own sibling, if they just had a baby, if they have worked with me for 20 years, if their spouse also just lost their job, if I know they might end up homeless, if they have cancer but no outside medical insurance, or any other horrible scenario millions of bosses and HR people have faced countless times.
15. I am OK with being socially cut-off and walking away from my friends when work beckons.
16. I love naysayers and I won’t explode or give-up when a family member, friend, customer, business associate, partner, or anyone for that matter tells me my idea, product, or service is a terrible idea, a waste of time, will never work, or that I must be a moron.
17. I accept the fact that I can do everything right, can work 70 hours a week for years, can hire all the right people, can arrange amazing business deals, and still lose everything in a flash because of something out of my control.
18. I accept that I may hire people that are much better at my job than I am and I will get out of their way.
19. I realize and accept that I am wrong ten times more than I am right.
20. I am willing to walk away if it doesn’t work out.

UPDATED 2-27-10:

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From the emails I have received and the comments here and on HBR I feel like many people have categorized me as a pessimist. In reality, if you look hard at this list of potential problems/disasters countless entrepreneurs have faced over and over, there is only one way to survive these and that is relentless optimism.

There have been moments, that I will be writing about in future posts, where I was 99.9% sure the company was failing, moments where my partner and I just stared at each other in defeat thinking the company was done. Every time though we would somehow find the will power to keep on pushing and never giving up. The only way we made it through those moments is our endless supply of optimism we both seem to share.

Also, as far as this list goes don’t think about it as a set of requirements that you must answer Yes to each and every one of these. This is more of a set of warnings to be aware of and cautious of and to keep in the back of your mind as you decide to enter the business world. To be an entrepreneur is to accept these problems and push onward anyway.

The second part of my post can be found here where I detail the 20 items in this list further.

Each time these things would work temporarily and I would get a brief boost but it would always fade. Finally I decided to try a to dig a little deeper and see if there weren’t some core reasons holding me back.

What I found were several critical aspects to the way I was approaching business that were askew.

# 1. I viewed business simply as a stepping stone to move onto greater things later in my life and therefore I was willing to postpone all my hopes, dreams, desires in the meantime to work 70 hour work weeks. I gave up on everything that made me happy, dropped all my hobbies, and decided that I could simply fast forward through my twenties for the sake of business.

# 2. I viewed business and fun as two completely separate things that could never mix. Work wasn’t supposed to be enjoyable and loving what you do was reserved for artists, musicians, and a lucky small bunch of other careers.

# 3. I approached work simply as that; work. I thought of it in these very finite terms that you go here, you do these set of things for 12 hours, you leave, you go home, you change into a completely different person and you live two completely separate lives.

So after that hard look at my life, I decided I was going to make some pretty drastic changes that might seem counter productive, but they have actually made a huge difference for me.

To combat #1 I decided I couldn’t continue without something fun and exciting outside work. I decided to take up one of my old favorite hobbies of photography (I grew up with a make-shift dark room in my basement). I went out and bought a decent camera and required myself to start shooting at least one interesting photo per day. I posted my shots to Flickr so family and friends could see and also to put a little pressure on myself to shoot often so I could keep posting continuous updates for everyone.

I also accepted that I was throwing away some of the best years of my life to go out and travel, enjoy friends, have some crazy adventures, etc… Your twenties are supposed to be your opportunity to be young and enjoy life in a carefree manor. Instead, I was living like some corporate 45 yr middle management guy having a mid-life crisis.

To combat #2 I started going out to lunches and after work drinks each week with the employees. The end result was a lot more camaraderie between myself and everyone else in the office and my overall enjoyment each day at the office definitely increased. I never would have thought that going to lunch would help my work performance, but the end result was that everyone in the office felt a lot more comfortable approaching me, telling me about problems they were having, and it built a sense of trust.

I also started to dedicate at least 30 minutes a day to doing nothing but reading my favorite business blogs, art and design blogs, and web design blogs. I have always been a creative person, but I had pretty much crushed all my creative outlets for the first few years of the company. I started dedicating time each and every day to nothing but learning about the latest trends in web design, advertising, and user interaction. The end result was my creativity at work increased significantly and I found ways to blend that into my work.

To combat #3 I came to the realization one day back in 2007 that I was two completely different people inside and outside the office. I ran into an employee outside the office on a Saturday night and they were shocked at how different I behaved when I wasn’t in “boss” mode. I was genuinely surprised since I thought I was the same person in the office as I was out. They replied that I was quiet, highly reserved, and lacked a sense of humor in the office and the person they were seeing that night was a much nicer person to be around and I seemed much more confident.

I took their comments to heart and made a conscious effort to loosen up around the office a little more. It didn’t come natural at first, but I was mindful of my attitude and demeanor around the office and if I caught myself being off-putting or melancholy or disheartening I would pause for a moment, take a deep breathe, and let my tensions dissolve away.

The end result of my actions in #1, 2, and 3 was a much more pleasant workplace for not only myself, but for the people around me. I don’t have to struggle to find motivation anymore like I used to and have found ways to make my work more interesting. I realize not all my tips can apply to everyone, but I am sure you can come up with your own interpretations of them.

We did $252,000 in revenue in our first year. Which would put us somewhere in the neighborhood of 0.005% of the industry wide revenue. Not exactly striking fear into anyone’s heart at that point.

When we would talk to these larger competitors about working together we would typically be told to come back in 6 months, if we were still in business.

So what did we do? We grabbed a phone and started calling everyone, everyday. We had a relentless attitude that if the industry wasn’t going to pay attention to us, we were going to force them too. We called and emailed every lead generation company, every major insurance company, every major insurance website, and thousands of insurance agents nationwide every day.

If they told us to wait 6 months, we  called back the next week. If they told us they would probably never do business with us, we told them yes they would and we would prove ourselves to them.

When you are the tiny new company on the block, no one will “give” you anything. You have to fight for every sale and every dollar of revenue.

No matter how small your company is, talk like your big. That’s probably one of the oldest rules in sales, but it really does work.

Finally we have gotten to the point where we are big enough and well known enough in the industry where the roles have finally reversed a little. Now it’s probably about 50% of the time going out and hunting down new business opportunities and 50% of the time these companies are now coming to us to try to negotiate deals.

It’s a great feeling to know that our amazing employees have created a brand that people now seek out and want to partner with. The hard work does payoff in the long run, but getting through those first couple years can be a nightmare. Remember, it’s worth it in the long run, so toughen up, grab that phone, and start making something happen.

To sum it up, I’m invisible in nearly any social situation. This does not bode well for business.

As time has gone by, I have had to learn how to adapt to a business world that not only demands that I be exceptionally outgoing, but requires that I do anything but blend in. To be honest, this could not possibly place me in a more uncomfortable situation. I’m miserable in social situations where I am the center of attention.

So, how do I deal with the stress of meeting business partners, attending conferences, business dinners, and conference calls? There is no elegant way for me to put it, I simply “survive”.

1. People want to talk to you: I try to approach any business interaction with the mindstate of, “these people are hear to talk to me because they want to hear what I have to say”. In reality, this could be the furthest thing from the truth and for many of the business interactions I have had, I was probably one of the least important people they talked to that day. However, to keep my confidence high and to prevent the social anxiety from strangling me, I keep reassuring myself that someone standing hear listening to me actually cares what I have to say.

2. It’s not that big of a deal. In the grand scope of life, I think we put way too much pressure business and money. There are so many more important things to worry about, that I really try to keep things in prospective when I feel the social anxiety starting to rise up. I remind myself that whatever situation I am in is just temporary, in the grand scheme of my life it will mean very little, and to just relax and try to be “in the moment” as much as possible.

3.  You’re not going to make a fool of yourself. Don’t worry about always sounding ultra professional. I find so much of my anxiety comes from my obsession with always coming across as professional, knowledgeable, and confident about anything someone asks about business, my company, or our industry. This completely unnecessary pressure is 100% self induced. You don’t have to have a witty answer, an insightful comment, or in-depth knowledge of every topic that comes across.  Don’t put that ridiculous pressure on yourself. People don’t like a know-it-all anyway.

4. Be yourself, but not for the reasons most people usually tell you. I’m not saying to be yourself for the chicken soup for your soul kind of reasons. However, in the business world when I say be yourself, I mean don’t distract yourself with trying to be something your not. I accept the fact that I’m very introverted, I’m a casual speaker, and I prefer one-on-one interaction. So, when I am approaching a business interaction, I talk like I have known the person forever and we are close friends, I talk casually without using much business lingo, and I usually single out one person in the group to focus most of the conversation toward.

That’s what works for me.

I would love to hear some other ideas on how to handle business social interactions.