Sequels can be a hit or miss, can’t they? You can end up with Speed 2 or The Godfather Part II .

You can either have a masterpiece, you can have a disaster, or you can have something in the middle. Seconds acts in life aren’t much different. I am currently entering my second act. After years in the medical products industry, I’m launching a new tech company, trying to find a good relationship so I can settle down, and I’m unsure of what all these new challenges will bring.

While I want this second act to be a success, there’s always a thread of uncertainty that runs through your mind. Even when it comes to dating, I’m well aware that dating someone who is starting a new company is a gamble. The smart women I gravitate to know that “startup” is a much nicer way of saying, “doesn’t have any customers” or “unstable future.” Stability is at a premium in the 30s dating scene. Will I find a romantic partner who embraces the uncertainties of that life?

My new company, Trylancer, is similar to online matchmaking. The premise is to hire top creative talent with small, custom work samples, giving businesses a realistic feel for what the freelancer can do. Scouring through resumes and profiles in search of a freelancer is a lot like using a dating app. Online profiles can be misleading, and you have to ask the same boring questions over and over. Actually, interviews are even harder because you can’t enjoy a drink if the interview isn’t going well.

Few things are scarier than starting all over again. This venture will show me what I am truly capable of achieving, and could also illuminate where I fall short. Will I be able to adapt fast enough to propel the company forward at the right pace? Will I be able to keep up with the technical lingo of the younger designers and developers who counsel me?

Sometimes I say a silent prayer for strength and insight. I’m scared my friends and family will laugh at me for building a company that is too dreamy. Right now, we plan to pay freelancers for their work, even if they don’t win the project. I’ve yet to find a single business adviser who thinks this is a good idea. I find comfort, however, in my favorite prayer in the High Holiday book Mahzor Hadash : “There is holiness when we are willing to be laughed at for what we believe in.” Even though my friends and advisers laugh at my idealism, deep down I hope they are on my side. I don’t want to fail when so many people are counting on me. Most of all, I’m afraid my sisters will lose faith in me because this concept is such a wacky one. I would never want to disappoint them.

There are always a lot of reasons not to do something, but I know it only takes one compelling reason to overcome your fears. If I don’t launch this company, I know I’ll regret it for the rest of my life. Just like many of our decisions that we are constantly faced with: at some point, we must decide to dive into our fears.

I’m choosing to gather up my courage and plunge in, knowing that, as Rabbi Zelig Pliskin said, “A person who takes a walk of 100 feet and a person who walks 2,000 miles have one major thing in common. They both need to take a first step before they take a second step.”

Falan Austin is the founder of Trylancer.com and lives in Chicago. He likes chatting with other entrepreneurs-drop him a line at [email protected] . He also tweets frequently say hello to @faustin.