Roadmap to Self Employment – Are You Cut Out for It?

Do you have what it takes to be self-employed?  It can look so easy from the outside looking in, but that is a total mirage because it barely provides a peek into what it really takes to run a successful business.

In Part 1 of this series, I talked about “How Do I Get There?” and the path I took from corporate employee to solopreneur.  Mine was truly an accidental entrepreneur journey.  Because of that I never gave a ton of thought to whether it was a fit for me or not (at least not proactively).  What I did do, however, was employ my secret weapon of conducting informational interviews with people I knew who were self-employed.  This gave me a great baseline of what to expect, expanded my network, and allowed me to get a peek behind the veil before taking the leap. 

That said, there is nothing quite like being IN it to truly get what’s required of the job.  When a mentor told me that self-employment would be the deepest, most transformational personal growth journey I could undertake, I thought she was exaggerating.  She was not kidding!  And the journey continues because as your business grows, you must continue to grow yourself over and over to that next level. So, plan on it being a lifelong journey of personal growth and be willing to get the support you need to do so.  If you try to be a lone ranger you will suffer along the way and likely fail.

When I wrote about the 10 red flags that signal you are not cut out to be your own boss, I focused on personality traits and habits that would likely set you up for failure.  Today, let’s look at who you need to be if you wish to be a success over the long haul.

Be Willing to Take and Tolerate Risks

Nothing spells risk like ditching a paycheck to blaze a new trail. When you are self-employed the risks never end: hiring team members, making investments, launching new products/services, becoming more visible, and the list goes on and on. It is never-ending.  That’s OK.  It’s part of the variety, excitement, and potential of taking the entrepreneurial journey.  The key is to take calculated risks and to be fully conscious of what you are doing, why you are doing it, and possible outcomes (from the greatest successes to the biggest flops).

Believe in Yourself

Without belief, nothing is possible. I’m not talking about airy-fairy wishful thinking here. I’m talking about a to-the-core confidence and belief in yourself and your ability to handle whatever comes your way.  Whether you work alone in your home office in a strictly virtual business or grace large stages your belief and personal presence will be felt by everyone. People make choices based on what they feel from you.  You will need to be able to maintain this confidence in the face of adversity and during the shittiest days in your business (and don’t fool yourself, you will have some of those).

Practice Excellent Self-Care

You are at the hub of your business.  Without you, there is no business (or at the very least the business becomes a lot less important).   While you may burn the candle at both ends at times, it cannot be your mode of operation.  You will burn yourself out, potentially get ill, and most certainly decimate the personal relationships that matter to you.  Remember, this is a distance run.  Treat it as one.


Speaking of distance runs, you need to be willing to persevere.  That looks like continuing to walk the path even when it is difficult and following-up far more than you might think necessary.  Plan on having a stash of cash to keep you going as you build.  One of the reasons I see so many solo businesses fail is simply because they ran out of cash and had to close their doors.  It takes time to get established, so plan for the worst case scenario and then add more working capital.

Create a Structure

One of the biggest joys about being your own boss is that you have total freedom over your schedule. Hurrah!  Without disciple, though, this freedom becomes your downfall. I see one of two things happen – the highly structured, came from corporate, high achievers (like me) tend to initially over structure themselves to the point that they hate their boss.  As I said when I hit this point – if you’re self-employed and working for an ass, you have only one place to look (hint: in the mirror). Or alternatively, the idea of freedom leads people to no structure at all resulting in a lack of focus and thus a lack of results.  Think of growing your business like you would a plant.  It needs a container in which to grow, but too tight of a container will kill it.

Seek to Learn

There is so much you can and need to learn about running a business.  If you don’t love learning new things, you will not thrive as your own boss.  As the Chief Everything Officer, there is never a dull moment. Always be willing to learn and budget time in your schedule to learn new things consistently.  That said; avoid the drinking from a fire hose phenomenon of trying to learn everything all at once (or trying to learn the things that you’d be better off delegating).  Focused learning and application.

Love What You Do

It takes a lot of time and effort to build a business. If you don’t love what you do, you should really just get a job.  Being clear about what you offer, why it serves other people, and feeling passionate about it is very important.  It is pretty hard to persevere if you don’t have any oomph behind it.  Passion and loving what you do provides the oomph.

Relax and Take it in Stride

Yes owning your own business is a choice not to be taken lightly. That said I was so terminally serious about what I was doing and the money part of the business when I first started that every day was a form of self-torture.  In today’s business climate being self-employed is not necessarily more risky than having a job (we’ve seen a lot of those vanish at the drop of a pin – so much for “security”, right?).  It is very different, though, so you have to be willing to roll with the punches and enjoy the journey. If you can’t enjoy the journey, what is the point?

Get Support

You are not meant to do this in isolation.  This is no time to try and figure it all out by yourself.  You have to be willing to invest in yourself and open to receive support.  Tap into resources and people that can help you shorten the learning curve and increase your chances for success.  You can find resources through local business organizations (for example: SBA, SCORE, small business divisions of your county, and local colleges); professional networking groups (women’s groups, chamber of commerce, etc.); mastermind groups; private, custom, individual support through coaches and mentors.

What do you think?  Are you cut out to be your own boss?  If you’re already  your own boss, what other traits have you found crucial to success over the long haul?  I’d love to hear your thoughts, experiences, and questions in the comments…

How to Become Self-Employed
Credit Image: Joel in Southern CA via flickr

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