Failed entrepreneur? Hope lives for your job-hunt


Dear Evil HR Lady,

My mom is 50 years old and is on the verge of losing her second startup in 15 years. Both cases are due to her partners (different people) embezzling money and leaving the company in more debt than can be handled.

She seems to have finally had enough of this whole scene and has asked me to do her resume for her so she can look for a job. I'm more than willing to help, but I'm concerned about her actual job options once we get her resume out there. 

Finally, I'd like to ask how we can write her resume? She was C-level in both the startups (as one can imagine), so the responsibilities are more or less given. But she tells me the achievements are less defined, because her business was mostly in distributing Hazmat [hazardous material] equipment and only did Hazmat certification sessions for free.

Does she have hope?

Of course she has hope! There is always hope, even though it seems like the economy has done its best to squash it like a bug. 

And speaking of hope, it seems like the two of you are working very hard to squash it even more firmly. This is a problem. You've got three big misconceptions going on here. Let's get rid of those so we can restore your hopes.

Because she was high-ranking, or C-level, executive, her responsibilities are more or less given. No need for false modesty. As an entrepreneur, your mother had all sorts of unique responsibilities. That's because C-level jobs are always different. When compensation specialists come up with salaries for C-level jobs, they don't just call up the competitor and say, "Hey, what are you paying your chief marketing officer? OK, thanks!" and then write that down for the salary.

In other words, your mother had specific responsibilities. She had specific achievements. Even if her day-to-day responsibilities were identical to every other person with the same title, her achievements are wildly different. Besides, a resume needs to focus on achievements, not responsibilities. This is the area of her resume where she needs to shine. 

Her achievement are less defined because she mostly.... Bah humbug. If she's only been a part of two companies in the past 15 years, then she can list tons of achievements. If not, there would have been two failures within six months. Often we see our daily duties as boring and therefore not true "achievements." For instance, she distributed Hazmat equipment. How much equipment? What kind of distribution? How big was the business? Were there ever any profits? How many customers did the company have? How did she get new clients? That is all-important, and it will also be important to a person considering her for a job.

The Hazmat certification sessions don't count because they were free. True, we discount free. But she did them and they do count, especially since her specialty was marketing. If she's looking for a marketing role, how did these free certification classes help her business? Did it bring in new clients or preserve existing relationships? How many people signed up for them? How did she publicize them? Did her clients pass actual certification exams? All of this information belongs on a resume.

It is true that it is somewhat difficult to make the jump from entrepreneur to employee. Many people will wonder if she just wants a job long enough to raise capital to start a new company. Assuming this isn't the case, she will need to come up with an explanation for why she wants to be an employee, rather than a business owner. And remember, there are challenges that go with being an employee, just as there were challenges with being the boss. It's hard to take orders from other people, and she needs to be prepared to explain how she'll do that.

It's also true that failed businesses are black marks on a resume. That's why it's so critical to focus on actual achievements. There needs to be a clear explanation for why each business failed and what she did differently with business No. 2 that shows she learned from the first business's failure. If her partners truly did embezzle funds, did she press charges? If not, why? She needs to be able to answer that question.

Because she hasn't had a boss, she won't have standard job references. Rather, she needs to get references from former clients. Find people who can speak about how she helped their businesses grow and succeed. 

Any good entrepreneur knows that marketing can make or break a business. You've got to get people interested in your business and products, right? Well, finding a job is like marketing yourself. A resume is a marketing job. When we market, we focus on the positives and the successes, not the failures (If you doubt this, watch television for a while. Ever see a Coke commercial that says, "Empty calories, plus caffeine! Plus, remember that grade school science fair exhibit where it dissolved teeth?" Of course not, because they are marketing Coke.)

Your mom needs to go into this job search with that mindset -- one that says, "Here are the absolutely best things about me and why you should hire me." Trust me, she can deal with the failure issues when they come up (and she will need to be prepared), but that doesn't go into the first stage of a job hunt.

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