SMALL BUSINESS, BIG DECISIONS

The freelance life is full of choices. The good news and the bad news is: they’re all yours. 

When there’s no boardroom of colleagues to vote on your latest proposal and no backing creative team to diffuse the responsibility, you are the sole recipient of both the risk and the reward. Going from acting at the direction of your superiors to steering your own ship takes a heady mindset shift — and a healthy tolerance for the unknown. 

If your self-employment journey has brought you to a crossroads, you’re facing the challenge of acting decisively and independently, with the full knowledge that life’s only real certainties are still death and taxes. Whether you’re making big choices or little ones, the what-ifs will drive you crazy if you let them. Here are our best practical strategies for organizing our thoughts, weighing our priorities, and actually making a decision you can stand behind.

The Worst-Case Scenario Exercise 

It may not seem like a very good idea for the already-anxious business owner, but hear us out. 

When it comes time to make a potentially impactful decision, our abstract fears often hold us back the most. If you’re living in wide-eyed terror of humiliation or failure, there’s no real problem to solve, which is… a problem. 

Let those fears play out in your mind. Look at all the options in front of you, and imagine what would happen if they each went horribly wrong. What does that look like? What do you actually stand to lose? Can you recover, and how? A lot of the time, our minds jump to a van-by-the-river scenario when we’re actually afraid of bad feelings. 

Imagining the worst-case scenario helps you think systematically about risks and their likelihood — all while reminding you of the safeguards you already have in place. It’s much easier to make a choice and move forward when you’ve already confronted failure realistically. 

Phone a Friend (But Not Too Many)

Sometimes another person’s technical expertise, experience, or even just their active listening can simplify a complicated-feeling decision. 

Think about what would help you get clarity, and ask for input from 2-3 trusted colleagues. Multiple opinions are helpful because they can help you discover whether there is a general consensus about the right path forward amongst people with relevant experience, but too many will quickly get overwhelming. 

Freelancers don’t have to operate in isolation by any means, but it’s smart to build your inner circle intentionally and be selective about the advice you attune to. Identify people whose perspective you value, and pay attention to how you react to their advice. You may realize there was something you “wanted” to hear — a valuable data point as you make your choice. 

Weighted Pros and Cons

Everyone loves the simplicity of a nice chart, but listing out pros and cons can overlook the fact that some cons are a lot more con than others. 

Some potential benefits are worth significant risks, and some risks don’t align with your personal values. If you’re seeking a more representative way to stack your options against each other, try assigning weight to each of the items on your list. 

Using a scale of 1-10, with 1 being the least important and 10 being the most, rank each potential benefit and drawback and compare totals. If terminating that contract early will add flexibility to your schedule (5) but is likely to get you sued (10), the decision doesn’t have to come down to which side of the list is longer. 

The Retirement Party Game

Heightened emotions can make it hard to be objective about high-pressure decisions. A little thought exercise can help you attain some distance. 

Imagine you’re a fly on the wall at your own retirement party. Fill the scenario with as much detail as you can — think about who is in attendance, what the room looks like, and what kind of food and drinks are being served. As you inhabit the mindset of future-you, looking back on all your accomplishments as a business owner, how does the choice that present-you is struggling to make factor in? 

Can you see yourself reflecting on that decision decades in the future as a pivotal moment in the future of your business? Does it make sense as a potential catalyst for other important developments? Does it seem unlikely you’ll even remember it at all? 

Thinking about how a single choice point fits into your life story doesn’t make it inconsequential, but it can ease some of the fear of being “wrong.” The longer view generally reveals just how constantly we’re learning, pivoting, and coming back stronger. 

Be Realistic About Urgency

Rushed decisions aren’t always great ones. Fortunately, there’s a good chance that the pressure to act quickly is mostly in your head. 

There are very few genuine creative emergencies in this life. Most of the time, our feelings of urgency come from our own discomfort with uncertainty. Not knowing what to do feels bad, so we assume that doing something will make that bad feeling go away. 

When something heavy is looming large, humans are known for seeking a sense of accomplishment anywhere they can get it. In practice, this can look like putting off a difficult conversation with a client by clearing out old emails or impulsively purchasing new bookkeeping software because you were overwhelmed by comparing product reviews. 

Sort out your priorities (and remember that time is your friend) with tools like the Eisenhower Matrix. For each decision in front of you, ask yourself 1) Is this important or unimportant? and 2) Is this urgent, or can it wait? 

When everything is an emergency, nothing is — learn to sit with the discomfort of self-doubt, and move forward at a pace that’s right for you.