Why “Upgrading” Can Feel Worse Before It Feels Better

Click here to sign up for our weekly newsletter

We’re halfway through the year, and it’s useful to reflect on what’s been achieved… and what hasn’t. I can honestly say that there have been some big wins, but there has also been tremendous frustration.

As a coach, I always urge people to put themselves out there. To not be afraid. To take a punt, to get over yourself, to step into the unknown. Failure is hard, but it’s part of success. It’s easy to say, hard to do. So I needed to also look inward, and fix the plumber’s toilet.

A year ago, I decided to take my own advice, and stop playing small. I started taking my hobbies (writing and golf) more seriously, and upped my investment in both. New equipment and a proper membership with golf, and higher levels of risk and marketing for the books. I can confidently express that neither investment has yielded tangible results as yet… with the exception that now, I have no excuses. Either I do the work or I don’t, but I can’t hide behind the grey of not trying.

Take golf. A total club upgrade has yielded occasional results, but my overall game has consistently gone backwards. It’s actually not that much fun compared to two years ago when I was rediscovering the game. But isn’t that also business? The first wild years are all excitement and adrenaline, but then once you settle things down and start upgrading systems and resources, it feels like you’re doing more work with less reward and it’s not as much fun. But experience also tells me this changes too, and when everything clicks, you hit a new level of experience and opportunity. So I’m going to keep faith.

In my investment business, I’m circling closer and closer to a proper equity stake in a growth business. Unfortunately, the opportunities I have seen so far have not qualified through my criteria, or they have gone cold before we could get serious about a deal. I ask myself the question, and this is like business or golf: Am I asking the right questions (or metaphorically is my swing sound)? It’s not enough to allocate the resources - how you build with them also requires you to tinker with your technique, and maybe there’s room for getting a coach or expert in to help take a fresh look.

In our operational businesses, it’s the same. We are looking at a new way for both the tourism business and for my coaching and training practice. In both cases, the answer lies in upgrading our resources and investing in growth… but knowing that results will not be immediate does make one hesitate, and the temptation to just hold out a bit longer is real. We’re bringing in coaches and experts to help navigate. And here’s why:

There are three big pains with growth.

People – you need to hire better, get more specialised in the roles, and build a system for consistency. And the hardest part of hiring is to check yourself for fit rather than chemistry, i.e. someone you really “vibe” with.

Systems – what got you here doesn’t get you there. Interrogating the way you’ve been doing things and doing the hard work to build a better way isn’t just a piece of tech or an SOP, it’s also the change management, the communication and the buy-in. It’s a pain in the ass, which is why so many of us hold on to old systems, and why so many new ideas fail quickly.

Marketing and sales – you build a bigger machine, it gets hungrier. And you need a consistent pipeline of business to feed that hunger, which means more intentionality around where and how you get your clients. Organic growth and great referrals is fine at the early stage, but doesn’t serve you once you get really serious.

Mind you, I’m having a tremendous time. I played an exceptional approach shot for a near-eagle on the 18th at the Lost City the other week, my training work has kept me very busy, the new book on the Ryder Cup is about to launch, I have learned a lot about due diligence this last month and things are picking up speed in terms of a level-up people structure in the travel business.

I exited the Greek training chapter of my life leaving behind a vibrant community that is seeing massive growth, and I do believe I had a small part to play in that. Now, July brings the opportunity to refocus on maximum impact on home soil, and that, in the end, helps me stay true to my charter.

PG’s Pro Tip:

Bring in outside eyes. You need good people who will give it to you straight, and help you navigate the complexities of life and business. And, taking my own advice coach, I think it’s time I got a swing coach. This is ridiculous.

Share on LinkedIn