The freelance life is full of uncertainties, and yes, fear. I should know, since it took my just 20 years to leave my “day job.” I’d had a side business of coaching and speaking for year, but going solo on this was a revelation. To honor the journey, here are some nuggets from the road: 5 Strategies for an Uncertain Future.
People often ask me if going out on my own is:
Scary? yep.
Exciting? absolutely.
Creatively challenging? HELL, YEAH!
Like Columbus, we’re all headed into uncharted territory—we’re navigating into the future. And like Columbus, we have a destination in mind, but are unsure of exactly how we’ll get there.

“Nobody knows how things will turn out, that’s why they go ahead and play the game . . . You give it your all and sometimes amazing things happen, but it’s hardly ever what you expect.”
― Gennifer Choldenko, Al Capone Does My Shirts
That’s certainly true of my career. I never expected to become a music career specialist or to have my own business, but from where I stand now, I wouldn’t have it any other way.
And Columbus? He was headed toward the East Indies to help the Spanish Crown secure the valuable spice trade routes. But oops, on the way he “discovers” a whole new continent. Unexpected outcome with results both good and bad, depending on the interpretation.
Career development can work the same way: we may be focused on a specific project (such as launching a new ensemble, expanding our teaching studio, or booking a tour) and we need to move ahead not knowing what the results may be, and deal with a wide range of outcomes along the way.
These situations call for courageous inventiveness. To help, here are my
5 Strategies for an Uncertain Future
1. Get accustomed to getting out of your comfort zone.
Watch this short Seth Godin clip on why and how.
Since there are no guarantees of results, you have to . . .
2. Plan the work and work the plan
Use the best information and advice you have available. There’s a terrific segment for those who hate to plan in Andrew Simonet’s Making Your Life as an Artist.
This means you need to . . .
3. Learn how to deal with unexpected challenges along the way.
Shit happens and you can’t let it derail you. Notice what helps you maneuver past obstacles and challenges.
4. Navigate as best you can based on interpreting the immediate results as you go.
We learn by doing. This means we ultimately learn to build and promote our ventures in public. Yes, there will be mistakes along the way—it goes with the territory. Perfectionism and trying to predict and control outcomes only gets in the way.
So we must . . .
5. Feel the anxiety and move ahead anyway. Inertia is the only real enemy.
Being a freelancer or “solopreneur” brings with it risks: maybe not shipwreck and drowning as with Columbus, but financial uncertainties and risks. It’s an emotional rollercoaster.
Smart (entrepreneurial) musicians take calculated risks: they figure out what they can afford to lose so that they don’t gamble everything. And they create beta versions of projects to test them and get feedback along the way.
So set your internal compass to your “North Star”— your ultimate purpose. If fear is stopping you from moving ahead (and it usually is what keeps people stuck), then ask yourself, what would Columbus have done? Or what would Gilda Radner have done?

Question: If you knew you couldn’t fail, what would you do?
Now: does the risk really need to keep you from doing that project? How can you minimize the risk?
Anytime we venture beyond our comfort zone we take a risk. Sometimes staying with the status quo instead of following our calling is the bigger risk: because we risk not fulfilling our life’s destiny.
for fun: check out this clip of Gilda Radner playing Roseanne Rosannadanna on SNL
Bonus help:
Another short Seth Godin clip: Uncertainty is not the same thing as risk
Lori Deschene’s 7 Ways to Deal with Uncertainty
Pamela Slim’s Confused about which of your inner voices to trust?
If you’d like to create a custom-tailored plan to move ahead in your career and life, let’s talk abut how coaching can help you. Reach me at Angela@BeyondTalentConsulting.com
Dream Big, Plan Smart, Live Well



