The Time-Travelling Agency Owner – Lessons From the Past to Change Your Future (Part 2)

business growth

Welcome back to the second article in this four-part series, detailing the biggest mistakes I made as an agency owner – and how you can avoid doing the same.

This week, we’re going to talk about one of the most common traps agency owners fall into: bailing out the boat instead of plugging the leak.

A Day At Sea

Picture this: you’re the captain of a small fishing vessel, and you’re out at sea with your crew. The ocean is calm. Waves gently lap against the hull of your small boat, a gentle breeze blowing past you. You can taste the salt in the air as you survey your surroundings. All is quiet. Peace at last.

But suddenly, there’s a commotion.

You look around from your post at the helm to see your crew all in a panic. You don’t know how it happened, but there’s water filling the boat at an alarming rate. Your crew are desperately bailing it out, but it’s pouring back in as fast as they get rid of it.

The shore is distant – too distant for you to hope for help to arrive. This is a job that requires all hands on deck, so what can you do but get down there and join in? If you don’t, you’ll be sunk for sure.

Everyone needs to do their part to keep things afloat – and as the leader, it’s up to you to shoulder the heaviest burden, direct everyone to where they’re needed, and even get down there and handle the work yourself.

There are times when this is the best approach. After all, life is unpredictable, and sometimes you don’t have a choice. But when you’re on your hands and knees desperately scooping out bucketfuls of water like your life depends on it, you’re blind to the reality of the situation:

  • All that water is pouring in from three small holes in the hull.
  • As long as these remain, the boat will continue to flood.
  • If you could just direct your energy towards patching these holes instead of bailing the water out as fast as possible, you’d return to a safe state that much quicker.

The captain that realises this simple truth can save his crew for certain.

The captain that gets caught up in dealing with the immediate threat in front of them (bailing out the water at the expense of correcting the root cause) is leaving their survival up to chance.

One of these is an effective leader… and the other is not.

But why is this relevant to you as an agency owner?

Because while you might not be the captain of a literal fishing vessel, you lead a team of your own (even if you’re just working with freelancers and other outside partners). And when your agency starts to take on water, what do you do?

Do you jump down and start bailing like a madman, shoulder to shoulder with your employees?  Or do you take step back and figure out where the water’s coming from?

How you answer will determine the success of your business. Sometimes the choice is out of your hands. Sometimes the best thing to do is to plunge in headfirst and lead by example, but other times, we simply default to this approach – even when it’s not the best move to make.

If you’re tired of being stuck in your business, then read on. You’ll get two tips you can use immediately to get some breathing room and start plugging the leaks, rather than getting bogged down in the bailing.

Tip #1 – Surround yourself with a great team

A lot of people are attracted to the idea of having their own business so that they have complete control over everything. Maybe you’re highly creative and very good at your job. In this case, it’s understandable that you like to be involved. You’re skilled at what you do, and you feel as if you can handle difficult situations better than your employees can.

But Apple would never have grown if Steve Jobs spent all day tinkering with computers and electronics. A landscaping company doesn’t grow if the owner pulls weeds 8 hours a day. And your agency won’t grow into the business it could be unless you can take a step back and become more like the effective boat captain we discussed above. From a detached perspective, you can make the right moves, not just the urgent ones.

During my 12-year stint as an agency owner, this was one of the biggest obstacles I had to overcome in order to grow my agency. Through my coaching practice, I’ve encountered dozens of other agency owners who had the same problem… until I was able to help them to conquer this issue and scale their businesses into something that worked for them (not the other way around).

Truth be told, I loved the work I did. I loved the process of engaging with new clients, landing new business, and delivering great creative work that generated big returns. Back in the early days, I was the key man in my agency, putting out fires and solving problems left and right. There was no limit to what I’d take on.

But over time, I started to enjoy my “key man” status less and less. I felt like a one-armed juggler trying to keep 12 balls in the air at once. Inevitably, some of them started to fall, often with negative consequences for the business.

My agency was suffering because I was trying to manage it all by myself… so the very first thing I had to do was to find a strong account manager. This simple step created some separation between me and the agency’s operations, which freed me up to focus on the bigger picture.

Managers can come from inside the business (i.e. you can develop and promote existing employees that have potential) or outside. Both are viable options – the most important thing is that they’re suitable for the position. We’ll talk more about what makes a great manager in another article, but don’t be afraid to go with your gut. Experience is the best teacher, and taking this first step away from low-level work is crucial in making your business into all it can be.

And if you’re not in a position to bring on a full-time manager (if you’re a smaller agency, or just starting out on your journey), then don’t be afraid to outsource some of your work to a freelancer (I use Upwork). If you don’t have the funds to take on a new member of staff, delegating to someone like this can be a viable option.

Tip #2 – Get Clear On Where You’re Going

After I had successfully detached myself from the day-to-day operations of the business, I suddenly had more free time to focus on where I wanted my agency to go.

And with all this free time, I soon realised that I wasn’t very clear on what I wanted.

As strange as it sounds, I had been so engrossed in running the business that I hadn’t stopped to consider where we were running to. All I had were some vague ideas as to the kinds of clients we wanted to serve, what we stood for, and how big I wanted the business to be.

Knowing your goal is one thing, but having a plan to attain it is entirely another. I didn’t have a precise destination in mind, so constructing a road map to get there was practically impossible. Like a ship without a clear course plotted ahead of it, my agency was liable to go around in circles – or even head straight for an iceberg that I didn’t spot until it was too late.  

At this point, I knew that I needed help once again – but this time, it was different. This time, I needed to sit down with someone and figure out what I wanted to do with my agency. So I did what I thought was best and hired a business coach.

He was local, recommended to me by a few colleagues. While I don’t remember the exact details of our meetings now (25 years is a long time!), I do remember that our sessions together put me back on the right track. I came away with a clearer vision of what I wanted to do with my agency, a plan for achieving these aims, and confidence that I could make this plan a reality.

This positive experience also pushed me towards becoming a coach later on in life – but that’s a story for another day.


The two simple tips I’ve described in this article have the potential to greatly improve your business when they’re put into practice. If you’re anything like I was, you love working in your business… but to grow and become all you can be, you need to set aside at least some time to work on your business. There will still be plenty of challenging situations, urgent problems and important clients that require your personal touch. However, being able to separate yourself from the day-to-day operations (at least every now and then) will enable you to take tremendous leaps forward.  

Getting an effective manager/management team in place is a vital step in freeing up your time to focus on the bigger picture. And if you’re not entirely sure what this bigger picture is, don’t be afraid reach out  for advice.

Gaining perspective from someone who has been in your position and advised countless other business owners just like you is the smart move. It’ll save you time and money, help you avoid unnecessary struggle, and help you to develop your agency into something that serves you in all you do.

Remember: the captain that chooses to bail out the boat alongside his crew is risking their lives…

But the captain that stays calm, spots the leak and moves to fix this underlying issue is hailed as a hero.

In our next article, we’re going to deal with the third mistake I made as an agency owner – one that has a huge impact on your business: choosing the wrong strategies. Stay tuned!

    Rob Da Costa