Win Some. Lose Some. Bid Again.

There is a particular kind of optimism required to own a small business. You see an opportunity. You read the scope. You immediately start imagining what you could do with it. Then comes the research. The phone calls. The emails. The vendor quotes. The spreadsheets. The creative ideas. The budget revisions. The second budget revisions. The “Wait—I have another idea…” conversations. 

Eventually, you hit Submit. And for a few minutes, it feels fantastic. Then you wait. 

Welcome To The Roller Coaster 

Sometimes you win. There is nothing quite like opening an email and seeing the words you were hoping for. Someone chose your company. They trusted your ideas, your experience and your team. You celebrate. Then you get to work. 

Other times, you lose. Someone else had a better price. A different approach. An existing relationship. Maybe they simply checked a box you didn't. Sometimes you never really know why. 

And occasionally, after investing hours—or days—into chasing an opportunity, nobody wins. The project gets postponed. The budget disappears. Leadership changes direction. The event gets cancelled. The dates move. The scope changes so dramatically that everyone goes back to the starting line. 

And all those hours you spent researching, planning, pricing and dreaming? Well... Welcome to self-employment. 

Freedom And Uncertainty Come As A Package Deal 

People talk a lot about the freedom of owning a business. And they're right. There is incredible freedom in building something of your own. 

We get to decide what opportunities we pursue. We get to choose the kind of company we want to be. We can work from an office, an RV, a hotel lobby or occasionally somewhere with a pretty spectacular view. 

We can chase projects simply because they sound interesting. We can have a crazy idea in the morning and decide by afternoon that maybe it isn't so crazy after all. 

That freedom is one of the greatest gifts of entrepreneurship. But freedom has a traveling companion. Uncertainty. There is no guaranteed paycheck arriving every other Friday. A fantastic month doesn't necessarily mean the next one will be fantastic. A proposal worth tens of thousands of dollars can turn into a signed contract—or a very polite email thanking you for your time. 

Meanwhile, insurance premiums, software subscriptions, licenses, memberships, certifications, accounting fees and all the other decidedly unexciting parts of running a business continue showing up with impressive consistency. Funny how that works. 

Losing Still Counts 

This might be one of the biggest things we've learned. A lost bid isn't always wasted effort. Every opportunity forces us to think. We learn more about destinations. We meet new vendors. We discover venues we didn't know existed. We build relationships. We sharpen our pricing. We figure out where we're competitive—and where we're not. Sometimes an idea developed for one proposal becomes exactly the thing another client needs six months later. Sometimes losing teaches us more than winning would have. 

That doesn't mean we enjoy losing. Let's not get carried away. 

There is absolutely a period after some losses when the appropriate business strategy is to grumble, question every decision we've ever made and perhaps use a few words that won't make it into the company blog. But then something else happens. Another opportunity shows up. And inevitably one of us says: “Ooooh. This could be interesting.” And off we go again. 

The Part I Wouldn't Trade 

Owning a business can be exhausting, unpredictable and occasionally terrifying. It can also be ridiculously fun. There is joy in creating something from nothing. There is satisfaction in watching an idea scribbled on a piece of paper become an actual experience. There is pride in winning work because someone believed our little company was the right company to do it. And there is something deeply satisfying about knowing that whatever happens next—good, bad or completely unexpected—we'll figure it out. 

That's proven to be a pretty good philosophy for business. And, as it turns out, for life too. Maybe that's the real secret of self-employment. You don't eventually reach a point where the uncertainty disappears. You just get better at riding the wave. 

The wins feel wonderful. The losses still sting. The cancellations still make you shake your head. And the opportunities keep coming. So you celebrate the wins. Learn from the losses. Pour a bourbon when necessary. And then? Bid again.

Cheers,

Bethany