Bad:

• /jobsearch/cover_letter.pdf
• /jobsearch/resume.pdf

One resume. One cover letter. If you’re only applying for one job, having one resume isn’t too bad, especially if it is a well designed resume. But your cover letter should be tailored to each company you are applying at and you should have an archived version of each as well.

The other big mistake here is that the person’s name isn’t included in the filename for either document, which gives it a very good chance of getting lost in the shuffle. Especially if the reviewer organizes things electronically.

Okay:

• /jobsearch/john_doe_cover_letter_design.pdf
• /jobsearch/john_doe_cover_letter_webdesign.pdf
• /jobsearch/john_doe_cover_letter_marketing.pdf
• /jobsearch/john_doe_resume_design.pdf
• /jobsearch/john_doe_resume_webdesign.pdf
• /jobsearch/john_doe_resume_marketing.pdf

This is actually much better. John’s full name is included in the filename for both resume and cover letter and he is creating multiple versions of each file based on the different jobs he is applying for.

Better:

• /jobsearch/design/john_doe_resume.pdf
• /jobsearch/design/john_doe_cover_letter.pdf
• /jobsearch/marketing/john_doe_resume.pdf
• /jobsearch/marketing/john_doe_cover_letter.pdf
• /jobsearch/webdesign/john_doe_resume.pdf
• /jobsearch/webdesign/john_doe_cover_letter.pdf

Here is where a simple change in the way John organizes his files can start to payoff. It’s the same set of files as in the last list but its no longer obvious to the person receiving the files that he is applying for different positions. Why does that matter? It’s the difference between hiring someone who does something well and is passionate about it versus hiring someone who does lots of different things and, well, they really need the job.

Best:

• /jobsearch/company-a/john_doe_resume.pdf
• /jobsearch/company-a/john_doe_cover_letter.pdf
• /jobsearch/company-b/john_doe_resume.pdf
• /jobsearch/company-b/john_doe_cover_letter.pdf
• /jobsearch/company-c/john_doe_resume.pdf
• /jobsearch/company-c/john_doe_cover_letter.pdf

This is the cream of the crop because it works whether he wants to specialize in something as specific as Interface Design or he is just looking for something creative. It also reflects the high level of detail he is putting into his job search. Because he should be paying a high level of detail. He should be researching each company he applies at so that he can tailor his resume and cover letter to them. He should be dropping one or two relevant facts about each company in their respective cover letters to demonstrate that knowledge.

I quit my job at the end of May. I took a two week vacation and then I went to work on my own business. As a web developer, I had to build my own website. As an entrepreneur, and a one-man shop as is frequently the case for the budding entrepreneur, I had to write my own copy, brand myself and market myself. When businesses responded, I had to sell myself and then close the deal.

The first month-and-a-half was spent on creating my image and the website (Studio Green) to go with it. I didn’t start soliciting business until around the beginning of August. When I quit my job I had no clients, no business plan, and no actual company. It was a huge leap of faith.

That brings me to the first requirement for a successful entrepreneur: balls. Cajones. You can call it by another name, but what it comes down to is that it takes a certain kind of person to toss the dice knowing that they’re gambling with their financial future.

For some people, like myself, there is almost no other choice. We don’t take orders well. I have a great deal of respect for the military, my father and step-father were both in the Air Force and my brother served in the Army, but I can guarantee you I would have been dishonorably discharged. It isn’t in my nature to follow blindly where others lead.

That I’ve only been fired once in my professional history is, quite frankly, amazing. There have been times when I would have fired me, had I been my own boss. This is a great place to point out that this article isn’t meant to be self-aggrandizement. Yes, on the one hand I have confidence, but I’ve also just pointed out that it cuts both ways. Having issues working under someone else can cause, well, issues.

So along with balls you have to know who you are. You have to be able to recognize both your strengths and your weaknesses. I’ve always had a strong work ethic and been extremely well organized (I’m hardcore obsessive-compulsive), but it turns out I’ve become very used to having a guiding influence. Left entirely to my own devices, I’ve floundered a lot in the first months. What do I do today? At times I had so many things to do that my brain just shutdown and I did nothing. Other times, I felt like I was really on top of things and I allowed my brain to shutdown and I did nothing.

A startup cannot allow that to happen. So I’ve taken to making lists. Lists help structure my day and provide concrete metrics for me to measure progress by: I can cross things off my list and write down how long each one took.

Okay, so we have balls and self awareness. What else? Intelligence? It can certainly be an asset against your competitors, but it turns out it isn’t the end-all. In fact, most geniuses lead very average middle-of-the-road (and income) lives and are quite happy working for others and not taking big risks. Your average successful entrepreneur isn’t dumb by any means, but tends to be in the average for IQ. That makes sense to me. It can be very easy to over-think things end up not taking enough action or taking the wrong actions. Doing can be more important than thinking in some respects.

As with all of my posts, I tend to ramble from one item to the next without much organization. I’m not being graded (unless you count readership as a grade), and I don’t have time to edit my book reports. Again, doing is more important. So consider this my segue to the next qualification: curiosity.

Curiosity may be the single biggest requirement for an entrepreneur and it’s actually the impetus behind this post. I had the opportunity to meet with another entrepreneur today, to discuss a possible business relationship. During the course of our conversation, I had the opportunity to ask him questions about how and why he started his own business. How long he’s been an entrepreneur, why he chose his particular service or product (note: I’m being vague because his business isn’t pertinent to the discussion and because I don’t publicize what business I’m seeking), and other questions. He probably felt like he was the one being interviewed.

The one thing that stuck out was his curiosity for a broad range of things that covered the gamut of his business. He is curious about the aspects of running a business, about his product/service, about the technologies behind his product/service, those used to produce it, the mindset of the people involved, his clients, their mindsets, the interrelationship formed by all of these items, and more. He is a jack-of-all-trades, master of none. He has a broad understanding of each area, but not the deep understanding that comes from devoting oneself to that one thing.

Dreamers often drift from subject to subject and have a broad range of interests. If you can turn a dreamer into a doer, you would have an entrepreneur. We have too much curiosity to sit still and do the same thing every day. But dreamers typically lack the energy and will, that’s why they are dreamers.

And that will be the last requirement to go on the list: energy. Under the self-awareness category, I have to admit that this is my weak point. Entrepreneurs are out pounding the pavement, shaking hands and kissing babies. Okay, that’s politicians, but take away the baby part, and you have an entrepreneur. They go wherever they have to go and do whatever they have to do to be successful. They have boundless energy, they are social creatures, and they thrive on challenges.

Me? I’m practically a hermit. That wasn’t always the case. When I was single and all of my friends were single, I went out all the time. But I was looking for something other than business. Now I’m married and I don’t have to go looking for love in all the wrong places. My friends, for the most part, are also married. These days I get out a lot less and I’ve gotten used to that. My sedentary lifestyle has had a crippling effect on my energy and drive.

That doesn’t mean I can’t be successful though. It means that I have an obstacle to overcome. All it takes is a little strategy, like making lists so I always have something to do. In my case, it means not networking through the local chamber of commerce and various local networking groups. I find them boring and stale and I have nothing in common with the other people there. (The ones I’ve been to were almost universally an older, more sedentary crowd with businesses that were decades, if not generations, old.) My time is much better spent hanging out with designers and artists.

The services I provide are split pretty evenly between designing and programming and I much prefer hanging out with the artists than the programmers. I found plenty of places to hangout, both virtually (Deviant Art) and in the real world (AIGA, Meetup.com). It turns out that a lot of designers have no designer to build websites for their clients and need to subcontract.

I don’t go to meetings or hang out at these places to solicit business. I go there to socialize, have a good time, relax, talk to my peers, and to just get away from my desk and my computer. But I recognize the business potential that also exists. I make sure I always have business cards available and I give them out to everybody. Networking and soliciting business is something you do 24 hours a day, seven days a week. That’s why being an entrepreneur takes so much energy: because you are always on the clock. What makes it bearable is that you get to pick what that is that you’re clocking in for. Pick something you love and you’ll be alright.

Your strengths and weaknesses will be different than mine. But if you can take an honest look at yourself and know what your strengths are and what your weaknesses are then you can play to your strengths and find solutions to your weaknesses. You just have to have the balls, the curiosity and the drive to do so.