Depending on what you are trying to do, on the surface doing it yourself isn't that hard. The trick is not to hurt yourself.

A training plan you download off the web for free or for a cost is still a set dummy training plan that you need to adapt to your own life. It also doesn't have any flexibility for situations like slight niggle injuries, random work issues that stop you from completing something, random circumstances that force you to miss a long weekend session, etc. It won't accommodate a planned vacation, or any other known restriction. It won't be able to help you when you have some specific restrictions that prevent you from getting, for example, all of the swimming in, but maybe you have time for extra biking.

That's where a good coach comes in. A coach can help you balance your schedule with your life, can update things on the fly when you have the inevitable misfire on a session, can tell you when it's OK to just skip vs when you should try to make it up, can rewicker the plan when things get derailed, etc. Especially if you are training for a number of different events throughout the season (vs a single goal event), a coach can help balance the training for the multiple events such that you get optimum performance at an appropriate number of them.

I think it mainly depends on your budget, your goals and your current level of ability.

Assuming that the plans you might buy or the coach you might hire are actually good then there should be a progression you can make starting out doing something on your own, then once having a level of fitness you could purchase a plan.

Those two options will have diminishing returns as you develop your fitness and ability in the sport. At some point you might reach a plateau using either of those options when it makes sense to move up to the next level of input/cost.

So it's hard to compare those three options against each other so instead I like to think of them on a scale. Sometimes a coach won't be able to get the best out of you until you are at a certain level so the return on investment might be lower than the return you get from just buying a plan, and on the flip-side at some point you won't be able to get the best out of yourself using just a plan. That's when a coach makes sense and the return on investment for a coach could be higher than that of a training plan.

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Cam Langsford, Founder at Training Tilt
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Good coaching, assuming it can be afforded.

Purchased training plans don’t account for many important factors, such as how you performed the day before, two days before a week before, what life responsibilities you have the next couple of day, a niggle, etc.

Good coaching, (emphasis on “good”) will take all of these factors into account to create an optimal training plan designed for you.

My coach gives gives me the plan every 3-4 days. I won’t know what I’m doing 5-6 days from today. It all depends on how I’m doing now.

That's the key that makes coaching worth it. It's the adaptation to reality that you get. "No plan survives first contact with the enemy". About half the athletes I coach I can give two weeks at a time, and they just put their heads down and do it. I only occasionally get comms from them saying something or other needs to change.

Others I might only write one week of training, and fully expect to change it on the fly.

I have one I only give 3-4 days at a time to due to lots of short-notice work travel and it works best for both of us if I don't bother putting workouts in for 5 days from now knowing full well it's likely to have to change. Some for work/kids/life, some for fatigue or injury.

The coach's job is to know this and anticipate it, and build the perfect plan for the athlete. And since no two athletes are the same, no plan is the same nor is it written the same way. There is a reason good coaching isn't cheap.

+1

I started out with free plans when I started out and did okay with those for sprint, Olympic, and my first few HIMs. But my goals and expectations were fairly modest at that point. Once I raised my expectations a bit, I trained harder but ran into the issue of not recognizing when to back off. Then I started adding in gravel events, other road races, and triathlons scattered throughout the year. It became a challenge for me to manage. Having a coach has made it all so much easier.