Given that the vast majority of companies are self-funded, it makes sense that many entrepreneurs choose to start their businesses on the side and grow them slowly over time.
Some moonlight in their new venture while holding down a traditional corporate gig, or use larger and longer freelance projects where the work might be ho-hum to balance out a growing portfolio of smaller, more exciting clients. Others rely on temp work or day jobs to cover their living expenses while they’re starting up a seedling business.
And I’m a big fan of the easing-in approach. For one, it helps mitigate the risk of starting a business, which generally allows for a clearer head and better, sounder decisions. It also allows you to taste entrepreneurship, determining which particular flavor is right for you. And it gives you the opportunity to get lots and lots of feedback from your customers and the marketplace before you’re fully reliant on your business.
But at the same time, having this crutch can also make you feel as if your business isn’t yet “real” and undermine your identity as an entrepreneur. Having another gig delays the inevitable “now or never” decision and all the urgency, commitment, and adrenaline that accompanies it.
Many entrepreneurs get too comfortable in this entrepreneurial purgatory—reliant on the safety and comfort of their employment, but unable to fully leverage the benefits and freedom of entrepreneurship. The question of when to kick the crutch and go full force into your business is always there, waiting to be answered.
So if you find yourself in this position, here are three questions to ask yourself:
Do I know what I need to know?
One of the primary benefits of having a crutch is that it gives you time and space to explore the market and learn about your business. When you’re not pressured to make things work (and make money) in any way possible, you can take your time being a student of entrepreneurship. What’s the response to your offering? How should it be priced? What are the best marketing and sales venues? Who are the most helpful peers and groups? What tools will make your business more efficient?
If you’re still figuring these things out, then by all means, hang on to that crutch! But, there also comes a time when most of the big questions have been answered. And at that point, instead of supporting you while you learn, your crutch becomes a hindrance that monopolizes your time—time that could be spent moving forward.
How close am I to getting more business?
Starting a business is a lot like gardening—it takes time to get a crop after planting the seeds. Even if you’ve built an amazing offering, created a terrific online presence, and told everyone you know about your company, you’ll likely still need to wait for business to start rolling in—at least at a predictable and steady rate.
Crutches serve as invaluable lifelines during this waiting phase. However, once your reputation has been established and business starts finding you, it’s time to reconsider your crutch’s value. Could you get more business if you had the time? Are you limiting how much you’re taking on because you’re overextended? If the answers are yes, it’s time to cut the cord.
What are the costs of my constraints?
Another way to think about the value of your crutch is to do a simple cost-benefit analysis. Consider the impact it has on your time, energy, creativity, and outlook. Is your day job affecting your ability to meet new people, make more product, or go above and beyond in ways that will drive more business?
I know a lot of entrepreneurs who, over time, begin to resent their “other jobs” for the impositions they cause. You want to preempt that—after all, that negative energy and fatigue won’t do your own business any favors.
But be really honest with yourself, too—most of the time, people overestimate the benefits of their side gigs and underestimate the costs. And it’s only after you identify the real costs that you can accurately assess whether the benefits truly outweigh them.
A crutch is there to support you while you set your business up for success. But once it starts standing in the way of that, it’s time to let go and do things on your own. After all, that’s why you became an entrepreneur in the first place.
