Sometimes when we’re on the brink of investing in ourselves, we can freeze or get stuck. In this article I share observations I’ve had with clients who have hit that inflection point, and ways we’ve navigated through their blind spots to a successful engagement in support of achieving their goals.
Adding some observations of my own…
Fear of Failure. I think you should modulate this with age and position from ‘bet the farm’ when you are young to ‘don’t put all your eggs in one basket’ when you are older while still maintaining a risk-on position. Nothing ventured, nothing gained. That is just how it is.
When you are young or in a position to lose everything (because you haven’t got much to lose) it makes sense to do one thing obsession with the mindset, “Failure is not an option”. You’ll probably accomplish a great deal that way and you’ll learn a lot from when things don’t work out. As you get older, have more responsibilities, and failure becomes more catastrophic then you can take the portfolio approach. That way none of the failures collapses the basket.
Lack of Confidence. As you say, ‘action sparks confidence’. You probably lack confidence in the first place precisely because you don’t know what lies ahead and need to take action to figure it out; it’s the action that conquers the fear of failure in order to build the confidence. If you are successful along the way, it’s the success that breeds confidence - and you’re never going to get the success unless you take the risk. And you’ll never take the risk unless you factor in failure as part of the process.
Financial Concerns and Risk Aversion. Pioneers seem more comfortable with things blowing up; they know they can always start again. Some people just have that kind of personality anyway, going from rags to riches and back again, multiple times over as if to deny themselves the comfort (and stagnation) of security and stability. If you are going to take a radical departure from the norm with the expectation that everything will change then you probably need to change yourself, too, or you’ll end up right back where you started.
Procrastination. One of my favorite pastimes! I don’t think it’s always such a bad thing but you probably need to interrogate yourself about it to make sure you are doing it for the right reasons. Speaking for myself, I have noticed that I have a habit of researching and noodling on something for a significant period until I am confident that I understand it enough to take the plunge. To other - more action-minded people - this is procrastination. To me, it’s simply preparation. When it comes time to take action, I am all-in because I’ve sufficiently convinced myself. I can think of someone else I know who is the exact opposite. They are constantly taking action but it has led to distraction and dissolution (in my humble opinion). They keep starting things that they don’t finish. I understand this. They have tons of ideas all the time and they can’t wait to get started - on all of them. Maybe one isn’t taking off as fast as they’d like it to so they start another, and another. I feel the same way but I kill most of them off early, spend a lot of time noodling on the ones I really like, and going with just a few in the long run. As are result, I have a reputation for consistency and tenacity because I only commit to what I can spend a lifetime working on. That’s what procrastination does for you.
Overthinking and analysis paralysis. Another favorite of mine. It rhymes with procrastination. But as I said in the previous paragraph, one person’s analysis-paralysis is another person’s R&D. Moderation is the key (like so many things). Analysis is great but it’s the paralysis part that’s the problem. And the paralysis part is driven by confidence problems - which can be overcome by taking risk. I like the approach wherein you run a small experiment to decide something. That’s a good small step that can lead to bigger decisions.
Comfort Zone. I have found serendipity to be a powerful force and it happens best when you do the unexpected, or sometimes when you do the thing you don’t want to do first. When I was a young man living in Japan and trying to get a job, I used to find interviews very nerve-wracking, especially as it wasn’t my first language. I particularly hated doing cold calls - even in my first language. So, I combined the two and started cold-calling people. One of them agreed to meet in person out of curiosity. They didn’t have a position at the time but they ended up introducing me to other people which led to better things. As a consequence of that experience, I crafted a policy of always doing the thing I feared or hated most, first. I didn’t keep that up forever but it definitely helped me break the ice.
Lack of Clarity. I solve this one with procrastination. I find that R&D helps immensely. But that’s just me 
Prioritization. This reminds me of “The Noble Sacrifice” that you explained to me recently. Might be worth inserting it into this conversation. I have never been particularly adept at this one, so I’m still trying to figure it out. In recent years, however, I’ve been far more curatorial about the time I spend with people and who gets time with me. It’s been very helpful because I find that some people are very demanding and depletive and this doesn’t help me with my GSD (Get Shit Done).
External Pressure. As a recovering ‘people pleaser’, I can tell you how liberating it is to not worry about other people’s opinions. Often one of the benefits of aging, so long as it doesn’t make you anti-social. Society needs a certain degree of conformity and norm keeping. Best to navigate a steady course down the middle, keep an even keel and not sway too far to either side. I’ve found it helpful to ask myself if I am trying to ‘be right’ or ‘do right’. The latter is preferable and frequently unpopular.
Past Experiences. This is how we learn and this is how we hold ourselves back. What a contradiction. Yet, this is pretty much what your whole post is about - taking risk to earn reward and build confidence - because there is an inherent contradiction to the cycle. Few want to take the risk in the first place.
If I were to condense this down to a simple axiom, it would be “no risk, no reward”. We can then ask ourselves, “What are the risks?” We can reframe our definition of risk, change the language that we use to label and identify the risk. We can reposition the risk, we can procrastinate the risk. Ultimately, we are asking ourself if the risk really is what we think it is. And then we can realize that there’s an even bigger risk from not doing anything at all.
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Thank you for taking the time to share such rich and insightful responses from your own experiences David. I’ve always observed that you truly have “a beautiful mind”, and your deep and honest reflections and musings here reinforce that (yet again). I’m so pleased this post provoked your thinking in such a meaningful way. This may be my favorite of our exchanges in this forum thus far! 
x
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