I recently was at the beach and watched seagulls flying across the water with large objects hanging from their mouths. Upon closer examination I realized that they had plucked seahorses from the waves. But they were struggling to eat them. To begin with, the seahorses were way too large to swallow. And there was no way for the gulls to tear them apart because seahorses have a tough armor-like skin. A few weeks later I watched another seagull flying with a large fish in its mouth while being chased by two more seagulls. Finally one of them stole the fish from the first (in mid-air!) but ended up dropping it in the water. The third retrieved it, landed on the beach and tried to swallow it – but the fish was too big.

All of this seagull activity got me thinking about an interesting issue that we entrepreneurs face from time to time. We often chase a piece of business that we very much want to win. Sometimes it’s a really, really big piece of business and we think to ourselves, “This may be way out of our league but why not give it a whirl? Maybe we actually could win!” Our pursuit of this business may be somewhat fanciful, but stranger things have happened and lo and behold we do win. OK, now what?

A number of years ago our apartment management business unit was pursuing a very large property management assignment. We had not previously done business with the prospective client, but the firm was well-respected in the industry. Months and months of relationship-building culminated in a “mystery” dinner with the client representative where we were told we were going to be awarded a large management contract. The client explained that a portfolio of apartments was going to be assigned to us but we couldn’t be told where the properties were located until right before we assumed management. The reason – the client was self-managing the properties and didn’t want the on-site or corporate office staffs to know about the management change until the day the company-wide announcement was to be made. We had also been told that the property assumptions would occur over a phased period of time – two or three months. When all was revealed we ended up with more than 3,000 units in 52 apartment properties scattered across the country. Oh, and they were dumped in our lap all at once with no phase-in. We were literally the dog that chased and caught the bus!

Needless to say, this assignment did not work well for us. It turns out that this client gave us all of the “dogs and cats” (tough properties) in its portfolio – so we were behind the eight ball from the beginning. Client expectations were unrealistic; our compensation did not begin to cover our costs, and our team was running ragged. After 18 frustrating months, we resigned the account at a loss of approximately $250,000.

What did I learn from watching the seagulls and my own experience? It’s very simple. It’s great to plan to catch a whale, but we must have a plan for what to do with the whale once it’s caught. There’s no question that the property management assignment I described overtaxed our resources. Unfortunately we had no idea how large the portfolio was going to be in the first place – we never should have put ourselves in that position. But as a quintessential entrepreneur I’ve often had the attitude, “Let’s just get the business and then we’ll figure out how to deal with it.” I’ve found that this approach is a great way to crash and burn. Pulling together the entire team for a series of planning sessions is paramount. Understanding how to scale our human and capital resources is vital. And sometimes we just have to say “no.” That’s pretty tough for an entrepreneur to do, but saying “yes” to the wrong opportunity could be extraordinarily costly.

Thinking big and pursuing big opportunities are part of our DNA as entrepreneurs. Comprehensive precision planning for the big wins paves the way for long-term success.

This blog is being written in tandem with my book, “An Entrepreneur’s Words to Live By,” available on Amazon.com in paperback and Kindle (My Book), as well as being available in all of the other major eBook formats.