Why People Sometimes Waver When Investing in Themselves (and some ways to navigate through these blind spots) (2024)

I’ve been serving clients as a Trusted Advisor now for many years – I’ve worked with business leaders, tech innovators, founders and entrepreneurs, family office members, rock stars and other creatives. Basically those who have made their mark (and those who aspire to), are keen to live their legacies today, and are ready to play full out.

These individuals are committed to making a difference, to achieving their sometimes lofty goals, and they realize they could benefit from having the right person by their side with the skills to help them craft a blueprint for the next phase of their journey, provide accountability to clear internal and obstacles that stand in the way of them achieving their goals, to share insights and envision possibilities they can’t see for themselves, and support them with creative problem solving around challenges large and small (professionally and often personally). They want someone by their side who has the gravitas, the expertise and the network to accelerate where they say they want to go.

That’s where I come in as a trusted advisor (in corporate settings often viewed as an “executive coach” to C-suite leaders), a thought partner, confidante, navigator, and even a “wing woman” of sorts. Sounds great right?

Not so fast! Working with someone like myself who holds the bar high in terms of co-creating with clients who are ready, willing and able to invest in themselves is just that; it’s truly an investment in both money and time. When faced with actually investing in working with someone who can help them achieve all of the above, sometimes people waver and pause.

When they do so (if it happens at first), it’s for several reasons. I thought it might be informative to share my observations on what some of these challenges are – and some ways I’ve supported my clients in moving through these issues towards a beneficial engagement, which inevitably serves them powerfully.

Here are some common factors that can contribute to this initial hesitation, and some considerations that I’ve helped my clients work through which have allowed us to move forward:

1. Fear of Failure: One of the primary reasons people hesitate to invest in themselves is the fear of failure. They may be afraid that they will not succeed or that the investment will not pay off, leading to financial loss and disappointment. They worry that if they invest time, money, or effort into a new skill or opportunity, it may not yield the expected results, and they will have wasted their resources. This can lead to indecision. I often ask clients whether they want to be beholden to these stories and perceptions for the rest of their life, vs our coming up with an actionable plan that will set them up for success on their terms effectively immediately.

2. Lack of Confidence: Many individuals lack confidence in their own abilities or believe they are not capable of achieving their goals (or even worthy to do so). This lack of self-assurance can make it challenging to take the first step towards self-investment. A lack of self-confidence can make it difficult for people to believe in their ability to succeed after making a substantial investment in themselves. This lack of confidence can lead to self-doubt and hesitation causing them to freeze rather than take the plunge. Paradoxically, we suffer fear, doubt and anxiety on the way to becoming successful. Taking action in itself often sparks confidence.

3. Financial Concerns & Risk Aversion: Financial constraints often play a significant role in the decision-making process. Big investments in oneself often require a meaningful financial commitment. They often involve taking risks, whether it's quitting a stable job to pursue a passion, starting a new business, or going back to school. Many individuals are naturally risk-averse and may hesitate when faced with perceived uncertainties. I work with my clients on a bespoke basis to address these concerns directly.

4. Procrastination: Procrastination is a common obstacle to self-investment. People may have the intention to invest in themselves but keep putting it off, waiting for the "perfect" time or conditions that may never come. As we know, the perfect time or circ*mstances rarely arrive – the best time to take action is now; often starting with taking the tiniest possible next step.

5. Overthinking and analysis paralysis: Some individuals tend to overanalyze their decisions, which can lead to paralysis by analysis. They may weigh the pros and cons endlessly without ever taking action. The antidote is to make a choice, get started, and keep going. Invite curiosity, creativity and possibilities to lead the way.

6. Comfort Zone: Some individuals are content with their current situation and may resist making changes or investments in themselves because they fear stepping out of their ‘nest’. Self-doubt is a big clue that they’re heading in the right direction; they’re willing to shake up the status quo and that’s where the magic happens.

7. Lack of Clarity: Without a clear vision or understanding of what they want to achieve through self-investment and why that’s important to them, people may struggle to take the first step. Insufficient knowledge about the path forward can create uncertainty and hesitancy. A set of powerful questions that I walk them through often results in several well-defined goals which can be all the motivation they need.

8. Prioritization: People often have competing priorities, such as work, family, and other responsibilities. Balancing these commitments with self-investment can be challenging and may lead to inaction. Ironically, people with these situations are often the ones who need support the most to be more balanced. Over the years I’ve had clients choose to put off buying an expensive car or vacation until next year in order to invest in our work together today to achieve the kinds of results that will set them up for success for the long-term.

9. External Pressure: Social and cultural factors can influence decision-making. The more successful they become, the greater the pressure to maintain or even surpass it. People may feel pressure to conform to the opinions of colleagues, spouses and friends, which can deter them from investing in themselves. OR they may become more isolated as they’ve gotten more successful and they now have fewer peers who truly understand their unique pressures and challenges. This can make it hard to ask for support, leading to a profound sense of loneliness. This in fact is one of the biggest opportunities to address. Successful, intelligent individuals have few people in their lives who are willing to tell them what they most need to hear. That’s where I step in. I understand their unique challenges and together we tackle them head on to resolution.

10. Past Experiences: Negative experiences or past failures can create psychological barriers that discourage individuals from taking risks and investing in their personal growth. I often address this by asking people what they’re tolerating in their lives and why. If they have a chance to craft a life of their dreams why wouldn’t they (especially if they’re not doing it on their own)?

Overcoming these hesitancies often involves addressing and discussing the underlying fears and concerns, gaining clarity about one's goals and motivations, seeking support and advice, and gaining the confidence to decide to invest in oneself.

This might include setting realistic goals, creating a focused action plan, and taking small steps that mitigate any perceived risks. It's essential to recognize that self-investment is an important aspect of personal and professional growth, and taking steps to overcome these challenges can lead to an enhanced and empowered life.

Why People Sometimes Waver When Investing in Themselves
(and some ways to navigate through these blind spots) (2024)


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