Guest post by Raven Solomon

I cannot swim. Wade maybe. Float, for sure. But swim? Not so much.

I was hesitant when I was invited to travel to Costa Rica and be part of a leadership development program that promised to teach me to surf. And surf as a way to strengthen self-awareness and my leadership? I was skeptical.

As a solopreneur focused on coaching and developing multi-generational workforces, I typically go to a place of solitude and I rely upon myself and myself alone. A good friend intervened, “There’ll be other people there. There’ll be professional instructors. Trust them.” She was right and the thought of relying upon others sounded refreshing and also challenging. This was the first lesson learned from the program and I hadn’t even said I would go.

Well, I signed-up and went to the program, where I did learn to surf, and also went through a series of scientific assessments to learn more about myself and my leadership, individual and group coaching, and participated in a service project to teach me about serving others.

It was surfing though that taught me about humility, overcoming fears, celebrating failures and embracing others. Here are six lessons I learned.

Lesson #1: You are not alone

Yes, this does sound like a cliché Michael Jackson song; however, for we solopreneurs, it’s an important reminder. Although much of the weight of our business is on our shoulders, we are not alone and we are not the only ones going through whatever it is you are going through. That’s called self-compassion.

Every time I entered the water, the surf instructors would gently and patiently remind me that I was not alone. My success was their success. My failure was their failure – and they wanted to avoid that at all costs. Knowing that I had them as a non-judgmental safety net gave me a sense of security and they continued to coach me even though my surf performance was quite terrible.

I reflected on the members of my professional network, friends, family, community resources, outside consultants, and so many more people who are available to support me. We all have them. These are the people vested in our success.

Lesson #2: Embrace the uncomfortable

For someone who never learned to swim, the ocean is about as uncomfortable as it gets. As adults, learning something new is the ultimate in discomfort. We get so comfortable in our cocooned routines that we sometimes forget what it’s like to push ourselves to the boundaries of our comfort zone and venture out to acquire a new skill.

Embracing my discomfort was losing the excuse of being too busy, letting go of my fear of not being able to swim and doing something I’d never done. And even though I failed a lot more than I succeeded, the pride and exhilaration when I got up on the board (maybe 10 times all week) was well worth the discomfort.

So, maybe it’s learning a new language or practicing a new sport. The options are endless and the reality is the same— getting out of our comfort zones and trying new things expands our thinking, pushes our limits and opens us up to new and fresh possibilities.

Lesson #3: Fail fast

When surfing, I quickly learned that regardless of whether you caught the wave or crashed, the next one is coming soon, and it might just be the biggest one yet. I needed to pick myself up, find my board, and push back out. Otherwise I risked missing the perfect wave – which is what I was seeking the whole time.

In a sport where you fail more than you succeed, resilience and learning how to celebrate failure is key. Entrepreneurship is quite the same.

We push out, we prepare, we feel like we’ve done all things right but the moment we step on the board, we crash. We could potentially spend weeks licking our wounds and feeling sorry for ourselves yet business has no time for that.

The next idea, the next product, the next iteration could be the right one and it could be here at any moment. Failing fast and resiliency are critical.

Lesson #4: Every wave is not worth taking

In surfing, discerning the waves worth taking is just as important as getting back up on the board when failing.

I noticed the surf instructors’ intense analysis and the study of wave patterns. They knew almost ahead of time whether the upcoming wave was a wave worth taking or if wait for the next one.

Wow. Surfing is based upon analytics and patterns which I quickly translated that into business. Not every opportunity is the right opportunity and not every possibility is worth pursuing.

Being strategic and applying judgement is vital to the sustainability of your business and yourself. Since the program, I’ve forgone multiple waves in my business that, in the past, I would not have had the maturity and strategic approach to forgo.  

Lesson #5: Set your failures to “Public”

Probably my twentieth time falling off the board and into the water, I noticed how quickly I would get up and look around to see who had witnessed my failure. The truth is I’m a perfectionist and perfectionist don’t like failing. As an ex-athlete on top of that, my immediate reaction was to protect myself from the opinions of others and to hide my failures in an effort to not appear weak in front of my “competition.”

There are some fatal flaws with that approach:

• Peers weren’t my competition, they were my support

• The instructors wouldn’t be able to give me proper feedback to improve my performance if they didn’t see me fail

• No one else could learn from or be comforted by the fact that I was failing too

• I’d push people away with a lack of vulnerability (a key leadership trait)  

After reflecting, I realized I was doing the same thing in my business. I would publicly celebrate the wins and conveniently set my failures to “private.”

I was inspired by my program experience to share failures and let in more people. Not only were they able to help me avoid the same mistake twice, it encouraged them to share experiences failing and bouncing back.

Lesson #6: You are a wise investment

As business owners, we are constantly spending money on just about everything outside of ourselves. We often see investing in ourselves and our development as a prolongable expense that belongs on the back burner until we have the extra cash to move it to the front.

Does that extra cash really ever come though, or do we find another, “more pressing” expense to cover with it? If you’re anything like me your answer is the latter.

If I’m honest, not knowing how to swim was only half the reason why I strongly hesitated to participate in the program.

The other half was not believing I deserved to make the investment in myself. I believed that there were far more important things that my business needed that were more worthy than spending the money on myself.

What could be more important to the business than a healthier, stronger, greater skilled me? I’d forgotten that as a solopreneur, I am my greatest asset and that investing in myself is the wisest expense I can incur. Making investments in my own personal development feels good and the return is evident.

The program I attended was called Leadersurf and it was one of the most rewarding learning experiences of my adult life. Conferences are nice. Classes and certifications are awesome.

There is something to be said about pulling away and building authentic connections with others, in an unfamiliar environment that stretches you as a person and as a leader. In today’s fast-paced environment, we need to be doing more of these things, not less. When I think back on my Leadersurf experience, it reminds us of what matters. It gives way for re-centering, intimate personal development and silent self-discovery. It is far more than just surfing.

It is life and leadership school on a board.