The Startup Juggling Act

How do we win the tug of war with time?

Richard O'Leary
CultureTech
3 min readNov 18, 2019

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This Egyptian wall painting from the wall of Tomb 15 at Beni Hassan appears to depict toss jugglers. Illustration from “Illustrerad verldshistoria” by Ernst Wallis et al, 1875

Have you ever noticed how calm circus jugglers look; as if they wouldn’t even notice if a ball dropped? Maybe it’s the same for entrepreneurs. Each one of the tasks at hand is important: which one to spend time on when? Where and when NOT to spend our time, at least at that particular moment? Startup leaders have varying tasks dividing up the days, weeks and months as they work to get a business off the ground. Business & technology strategy, investor pitching, technology development, talent recruiting and managing- all are central. And so much of our time must be spent cultivating, selling to and learning from customers? Having spent many years in the advertising (aka marketing services) industry, I learned juggling becomes a means of survival: simultaneous management of clients, pitches, campaigns, distributed global teams, P&L’s, quarterly/annual plans etc.

There is an old adage: ‘if you want something done, find a busy woman to do it.’ We all need to emulate busy women and strive to model our behavior in their likeness. I have a 93 year-old Mother who has always been and continues to be busy and productive. I have been striving to match her juggling skills my whole life and still have not quite gotten there; but strive, still, I do.

So, how do we mere mortals win this tug of war with time? As is often the case in life, the very problem presented to us conceals the opportunity.

Juggling many balls is the foundation for developing a keen sense of priority and patience. Of course, keeping a highly organized to-do list and calendar, having a clear plan; these are key tools. But they can also enslave us. When that customer meeting gets cancelled, that investor prospect we have met with several times suddenly disappears, when scope creep in the product development plan rears its ugly head, we tend to punish ourselves for the lost time. In fact, what we lost in time, we gained in learning if we keep our big priorities in focus and our patience in hand. How many times do we document the learning from a lost prospect, project scope creep, a customer who says no?

Famed hedge fund leader and entrepreneur Ray Dalio often says: ‘Be radically open-minded.’

Ray Dalio — GETTY IMAGES

Read ‘Principles’ by Ray Dalio

I’m beginning to believe when bad things happen to us as startup leaders, that is our chance to practice what Mr. Dalio is preaching. How can we open our minds to learn from mistakes, failures and just become more patient as people? The leading consulting firms normally perform a ‘postmortem’ on projects; both the successes and the failures. How about we perform ongoing postmortems on our time with as much discipline and focus as we plan our time going forward?

Finally, with whom do we spend our time? The customer, of course; our team, naturally; investors, influencers- yes, all of them. For me, time with everyone and anyone that can help me better understand how I can make the business a success is time well spent. I relish lots of one-on-one conversations with team members, with customers especially; investors, and very often, people who just care about what you are doing, have no stake in it, but just want to help you. I am learning to be patient and allow myself time with a lot of people with no vested interest in the business. They are often the most honest and supportive: they know that’s what you need.

So, fellow entrepreneurs: let’s actually spend the time. Let’s not worry about wasting it, let’s be patient with it, and most of all, let’s learn from it. None of it is really wasted if we don’t waste it.

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