Career Advice Tuesday – “So You Want To Be the President?”

February 21, 2012

Dear Infosecleaders:

I am writing to you as my last sounding board, as I believe that I have made the decision to leave the world of “employee” for the career of “1099 information security consultant.” 

I have arrived at my decision due to the fact that I am frustrated working at my current employer.  I worked for a boutique professional services firm, where I am the only person who delivers my specific type of technical information security services – application security and code review.   All of my co-workers do a lot of policy, compliance and governance work – and my firm has a pretty large PCI practice.   

My company likes to tell its customers that we are adept at performing technical security assessments, web application tests, and code review – but in this case, in essence the “firm” is “me.”  When our sales team sells work, my phone rings off the hook.  This means that I am responsible for additional travel, RFP’s, delivery, and reports – much more than my other colleagues whose skills are repeatable and more plentiful.  Although I am unique, my compensation is not, and I do feel underpaid. 

 My thought is to start my own business, leave my current employer and offer them to use my services to their customers as a 1099.  This should enable me to earn additional monies and give me some flexibility on the projects I want to work on.  Upon completion, my plan would be to partner up with some others independent consultants, and try to find additional work.

I figure that in the end, if it does not work out, I can always get another job with a services firm similar to my current employer.

Do you have any words of wisdom for me?  I have always wanted to be the president of a company, even if I am its only employee.


Mitt Santorum


Dear Mitt –

The first thing that I will do is to agree with you.  If you decide that you want to leave your current consulting company, to begin your own venture, you most likely will have very little risk.  If you decide after a short period of time that you do not like working as an independent, you can always go back to the work force and attempt to find a job.

However, I am going to caution you to think through your decision a little bit more thoroughly and begin to think of the bigger picture, which is your career.   A decision to leave traditional employment and enter the world of independent contracting is great, when your skills are in demand and the market is hot – but good times do not always last forever.   If you decide to take this route, you need to be cognizant of this – and make sure that you continue to invest in yourself and your career, and make sure that you remain on the leading edge of your subject matter expertise.

One thing that you may or may not be aware of is how good your skills are in comparison to the remainder of the market.  In your company, since you are the only one who does what you do, you may be the “big fish” in the “little pond.”  Your skills may only be viewed as “outstanding” because of what they can be compared to.

In order to truly be successful as an independent consultant – you have to be exceptional and unique.

Before deciding to step out on your own, my advice would be to join a firm that has an area of specialty that aligns with your core competency of application security and software review.   I would select one of the smaller boutique firms – maybe one that has between 10-30 people – who are known in the industry for their expertise in this area.     The first indication of your talent should be your success in the interview process.  These firms traditionally hold a high bar for talent, passing these obstacles with a good degree of ease, should be the first indication that you have talent.   Then, upon joining the firm  – I would treat your employment like it was your own business and incorporate all of the elements into it – delivery, customer management, and sales.

See how this goes for a year or so, and see how successful you are, in all of the stated components.   You should be able to have enough data to understand if you would be happier in this type of environment or out on your own as an independent.  At the end of this experiment, you will definitely be able to make a more informed decision about your future.

Regardless of your choice, you are always the President of your own career, and the CEO of You, Inc.

Good luck,

Lee Kushner

Posted by lee | Filed Under Advice, Behavior, Career Advice Tuesday, Planning, Position Selection, Resume, Skills 


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