Should-Free Living by Heather Strang – Freelance

Heather Strang, and co-author Brooke Emery, wrote the upcoming book Stop Shoulding On Yourself! A Woman’s Guide From Obligation to Inspiration. The book encourages women to live from an authentic and should-free space.

So, grab a cup of tea and read on…who knows, you just might find some great ideas for your own life…

Dear Heather,

My should is this: I should stay at my 9-5 job to pay my bills, save money and be responsible. The trouble is I fantasize about going freelance or starting my own business….though I’m scared of finding the money to make it work to survive. My burning question: how do i become my own boss??????

Dear L.H.,
It’s an age-old question, one that many of us battle with. Do we follow our heart (in your case to have our own business) or continue to follow what everyone else is doing (i.e., work for “the man” in corporate America)? The thing is, it’s different for each of us. Some of us were born to rock our own business, while others prefer to be part of a larger team. Either way, there´s no wrong answer. Just dig within yourself to identify what´s authentic and what is merely a “should”.

And here´s some perspective: working for yourself and having your own business doesn’t mean you won’t be able to “pay your bills, save money and be responsible.” In fact, you can do all of those things and run your own freelance business.

If your heart says you need to be your own boss, then by all means—begin making preparations to do so. The “should’s” tell us to ignore these inner urgings and instead chide us on the importance of “being responsible”, which apparently involves only doing what everyone else is doing. If 9-5pm in a cubicle doesn’t make your heart sing, then it’s time to find what does.

Here are some tips on how to get from “How do I become my own boss?” to actually becoming your own boss

-Allow yourself to dream. Journal about what your business would look like, who your ideal clients would be and what type of flow you´d like each day to have.

-Perform an informational interview with someone who is successful in your field. Pick their brain—how did they do it? What were the challenges? Joys? How did they get through the hard times?

-Hire a coach to start making this “dream” a reality. A coach can help you make this big picture dream a reality by breaking it into tangible steps and providing the additional support you need.

-Start visualizing yourself as your own boss. Create your office—either in your home, or begin looking for other space options. Print up business cards, and overall begin acting as if this “dream” is already your reality.

-Start applying for contractual freelance gigs that would bring you a step closer to being your own boss.

Most importantly, realize that your “dream” would not exist inside of you unless there was a reason for it to do so. You long to have your own freelance business because that is, in fact, what you are meant to do. Now, show the “should´s” who´s boss and go out there and get it!

Much love & blessings,

Have a question about this topic or any other? Next month we’ll focus on the should’s surrounding your MONEY. Send your questions to: