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5 Questions to Ask Before Going Freelance

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Recently I took the big leap to going consulting / freelance with my career.  This was not an easy decision by any means and made even more difficult by having a great job with some pretty incredible people.  Going freelance should not be taken lightly.

Going freelance is not for everyone and I have to admit, I had my reservations.  I have worked for other companies my whole life starting from when I was a kid delivering newspapers for the local paper growing up until now as employee #7 at a pretty incredible start-up right here in Portland, Maine.

I have been extremely fortunate in my life to work for some great companies and with some incredible individuals.  I could never replace all the great experiences my professional career has given me.  Every job has taught me valuable lessons, which will ensure success as we move forward.  One of the biggest examples is the Navy was great in building the confidence to know we can do anything if we want it bad enough, especially if you have great people around you (family, friends, and mentors).

Leaving was extremely difficult for me since I actually helped to build Vets First Choice over the past 5 years.  What an amazing journey and incredible experience to be part of a start-up at the very beginning.  Not many people get to say they were employee #7 in a very successful company.  Luckily I will be able to wear that badge of honor for many years after this experience (I helped build that).

You want to go freelance, what are the five questions you should ask yourself before making the jump?

  1. Are you debt free?  I feel this is a big one as we are leaping into the world of no guaranteed income vs. a known paycheck every so many weeks.  If you and your family are debt free, then that is one less worry on your plate.  It reduces the need to make a high income right off the bat and allows you to build up your customer base.
  2. Can you get health insurance?  Health insurance is a big issue for families.  We need to have some insurance in order to protect what we have built.  Not having insurance is not an option, since one Murphy issue could cause chaos in your emergency fund and other assets including your home.  Health insurance has changed a lot lately and I can probably write a post just on this topic alone from what we have learned over the past couple weeks of research.  I will share our learning in a future post.
  3. Do you have 6 – 12 months of living expenses set aside?  Taking a leap into freelance means taking an initial hit in income for a little while until we build clientele.  If you have your emergency fund built up, you will be able to sustain the short term issues while you build your business.  Don’t worry, if you push hard and are aggressive, you will gain back that income before you know it.
  4. Does your spouse have an income?  If you have all your debt paid off and your have your emergency fund, that is great.  If your spouse also makes an income that is even better.  Your spouse can pull the slack while you build your client base.  The best part of being a family is the ability to get through opportunities and challenges as a team.  Alone we only as strong as ourselves, but with a partner we are twice as strong.  We have been building my wife’s business over the past 5-7 years and that will help the transition for us to be much easier.
  5. Are you willing to be uncomfortable?  Probably the biggest one of them all, since you now have to generate your own leads and get your own business.  Are you willing to make cold calls, walk into local businesses and send emails out to companies unsolicited?  As a freelancer you are your own sales team, marketing team, finance team, and operations team.  We do everything and that sometimes includes the things we may be a little uncomfortable with.  It is okay to feel a bit uncomfortable and over time, it will get easier.  If you are providing a valuable service to organizations, you will get business.

The power which resides in him is new in nature, and none but he knows what that is, which he can do, nor does he know until he’s tried.  – Ralph Waldo Emerson

Now it is time for our family’s new journey to begin.  We have already taken that very difficult first step forward towards our professional independence.  If you have read anything by Dan Miller, he actually believes working for one company is much more risky than working for yourself.  If you have 5 companies you do work for and one decides not to continue with you, you only need to replace 20% of your income.

The why we move to freelance is a post for another day, but there are a myriad of reasons many of us go this route.

Have a great day!

{ 1 comment… add one }
  • Aleksandra April 15, 2015, 10:51 am

    The most important tip for new freelancers, is having some money in a savings account before you start your freelancing journey, it’s very important. When I started freelancing, I literally had all the things on this list blank, except the first one. I didn’t have a savings account, or a spouse to support me financially, and I sure as hell didn’t know how to deal with clients, but luckily for me, it all worked out well. So make sure you have at list three things on this list checked, so you can avoid stress and frustration.

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