While I was wedding planning, I found a great website: It offers sane wedding advice and a lot more besides. My favorite essays there deal with balanced relationships, thoughtful decision-making, women in the workplace, and entrepreneurship. Today there’s a discussion about roadblocks — the real barriers and self-imposed excuses that keep us from achieving what we really want in business and in life.

You all know about my goal to become a full-time freelancer. It’s been almost a year since I first posted about it. Today I have one regular client and a few Elance jobs under my belt, but other than the tax bills I just paid (OUCH) there’s not much evidence of progress. So what’s standing in my way? What are my roadblocks?

I’ll be honest: there’s a lot of fear. Fear of leaving my team in the lurch when I quit. Fear of failing to earn enough money. Fear of networking. Even fear of too much success — attracting so many clients that I get overwhelmed with work and can’t execute any of it well, ruining all my contacts and overworking myself into misery.

In the past, the best way for me to overcome roadblocks has been through research and preparation. Entering new situations unprepared makes me incredibly anxious. So I have learned to set myself up for success by picturing in detail how things will happen. If it’s a job interview, I can try on the outfit I’ll wear and drive to the location the weekend before, just to make sure I’m familiar with the place. If it’s my wedding, I can fill out the license application ahead of time so I don’t make a poorly considered choice on the spot (like my coworker who wasn’t prepared to decide her name change when she went to get her marriage license — she thought she had until the wedding date). If it’s woodworking, I can sign up for a workshop at Home Depot before using my new power tools at home.

The problem comes when research and preparation stop me from taking action at all. I’ve been reading articles and books on freelancing for several years now. I’ve created budgets in interactive Excel spreadsheets. I’ve done actual freelance assignments for actual clients. Still, I don’t feel prepared to take the leap.

Some practical roadblocks did clear last month when I married Dan. As his legal spouse, I’ll be able to go on his health insurance policy when I quit, at a much lower rate than private insurance. I also get the official commitment that he can support me financially if my income starts out slow. What’s his is mine, even more than it was before, and that’s really reassuring. Plus, my freelancing business and website carry my full name. I had worried about the problem of rebranding myself if I married and changed my name long after my business was established. Now, though, I can make that transition while the business is still in its baby stage. I’ve already bought the new URL and started working on a site migration plan.

My biggest remaining roadblock seems to be the false belief that I can and should be 100% prepared for everything. Of course nobody advises abandoning your day job without any safety net. But maybe I’ve done my due diligence. Maybe it’s time to gather my knowledge and climb over this roadblock with confidence, even though I can’t clearly see the other side.


2 thoughts on “Roadblocks

  1. so hey, i quit my job today, you should do the same. you know, in solidarity. what better reason do you need? (well, besides the fact that you HAVE done your due diligence, you do have a supportive partner, and that you will absolutely ROCK. IT. OUT.)

    personally, i think life is effing terrifying. there will always be something on the horizon that you don’t feel prepared for, no matter how much research and planning you put into it. i’m not sure that feeling will go away any time soon, given all the milestones we have yet to pass. and sometimes i think the anticipation and preparation stage is more stressful than actually going through with the actual plan. you know, too much time overanalyzing all the “what ifs.” maybe it’s time to give yourself a break from all the mental anguish and just DO it.

    • Hey! I’m so happy you did that — hooray to taking back some of your freedom!!! Your words ring so true. Despite solidarity, today isn’t quite the right time for me to quit… But once I pass that important milestone at work that I told you about, GAME ON.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s