Smooth Seas Do Not Make a Skillful Sailor, 5 Ways to Turn Trouble into Triumph

June 25, 2021

The T-Minus Team

A phrase that stands the test of time because it should, rings true in the software engineering world. A notion near and dear to our own founder, Craig Ceccanti, he reflected about his life experiences on the water to that of his experiences as a startup founder. Growing up sailing with his family, Craig learned a lot about “cause and effect” and the “domino effect” as it related to successfully sailing. He talked about the many times they had to prepare for a “man overboard” emergency and attributed much of his preparedness in business to those early days.


Accepting that an entrepreneur can’t always prevent error or issue from happening and instead leaning into preparation for organized chaos will help to isolate issues. This can stop the issue in its tracks before it has time to compound other areas of the business such as company culture, or buy-into the company’s mission.


Beyond just the software project itself, entrepreneurs and startup founders want to get comfortable with this mindset of becoming a“skillful sailor” and Craig gave us 5 reasons why:


1. The quicker a founder learns the art of chaos, things going wrong, timeline delays, miscommunications, the quicker that same founder can embrace the importance of operational efficiency. While not an end-all-be-all fix, operational efficiency allows a founder and team to better prepare for what happens next, and that’s when things get fun.

2. Now don’t go looking for trouble there but “expect the unexpected”. Take an open inquisitive mind to learning through the problems that inevitably arise as the business gets off the ground. Ask why they happened and grow together as a company. It can be easy to go on the defensive or sometimes attack when issues happen. Stay focused on keeping a good attitude, staying positive, and finding a resolve.

3. Document problems that happen in a way you can go back to, revisit, use to enhance process and procedures over time.Documenting things is also a great way to notice emerging patterns in behaviors which can help you pinpoint where or how the issue is happening.

4. Reverse-engineer the successes you’ve had for the business to better understand how to repeat those processes. Think about what went right, what was most effective, how was the team communicating during that successful project for the company? There is great insight in stopping just long enough to stair step processes both in times of success and in problematic moments. Never for the sake of pointing fingers or claiming fame, these outlines raise up the entire team to be better prepared next time.

5. Stay curious. Sometimes when even the littlest thing starts to go wrong, it can mentally drain an entrepreneur who is stretched thin, fighting for mindshare in her/his own brain and constantly prioritizing what comes next. Anyone knows that mental or physical exhaustion compromises a person’s ability to fight the good fight. Committing to a curiosity about how to keep making the business better is a great way to encourage mental fortitude. It takes a lot of it sometimes.


Starting a business is not for the faint of heart and as fellow entrepreneurs, our team stands in support of anyone who wants to“start”. What happens next is where the success of the business gets challenged and T-Minus Solutions is here to help as a stand-in CTO and software development firm for those non-technical or spread-too-thin entrepreneurs who want to grow the right way.

The T-Minus Team

Building software projects the way they should be done; predictably, strategically, on task. Very importantly, let's have a good time while we do it!
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