Ask Maynard: What’s Holding You Back in Your Career?

June 2nd, 2015 / Comments Off on Ask Maynard: What’s Holding You Back in Your Career?

At this stage of my life, everything I do is focused on helping people get better. In my investment work, I spend time picking which entrepreneurs I believe in that are working on impactful ideas. Through Everwise, I am focused on helping people grow in their careers.  With my board work, I’m helping bigger companies reach their potential while also staying relevant in the corporate world. In my non-profit activities, I am focused on helping underprivileged, hard working teenagers get to college.

All of this happened organically. As my career grew, I found that I was spending more and more time providing advice and counsel. I had always been willing to provide help to others, but early in my career, no one was really that interested in what I had to say! Now, the demand for advice far exceeds my individual capacity to handle it. Hence I’m always looking for ways to provide insights and advice in a scalable way. My book Rebooting Work: Transform How You Work in the Age of Entrepreneurship was a first step in this direction. It didn’t seem enough and that led me to co-found Everwise. I’ve also enjoyed writing on LinkedIn Influencers as a way to try and help share what I’ve learned.    

I have been itching to create an Ask Maynard forum where the community can ask me questions they would like answered on different topics (career, entrepreneurship, management, etc.) Each week or so, I’ll take the questions that resonate with me the most, and publish my answer. I’d love to ask the community to help me decide which questions to answer and also what topics they would most like to address. Please ask your questions in the comments — and please also upvote the questions you like best!

I’ll tackle a new theme each month. This month, let’s talk about your career and what could be holding you back. I believe that we are all CEOs of our own destinies — we are the owners of our careers and we can’t cede control to anyone else. I also know that may be easier said than done.

Let’s get started with our first question:

Dear Mr. Webb, I dream big but I’m afraid that I lack actions and executions (for some reason…). I could never define this. The years go by, and it seems like accomplishment isn’t anywhere near… Any advice?  — Maria Eleftheriou CFTe, Technical Analyst, Forex Trader at AristionFX

Dear Maria, thanks for asking your questions.

Frankly, dreaming is far easier than doing. In my opinion, to achieve one’s destiny, you need to be aware of what is possible (the dream piece of the equation) and then committed and bold enough to take the actions required to achieve it  (the do part of the equation). Like many things in life, it is easy to say what should be done, but hard to do what is necessary. Think of how simple it is to give someone else good advice as opposed to incorporating that same advice personally!

While I seem to do well with many of my business goals, I’ve struggled throughout my life with weight. It’s always on my task list, and I work out regularly, but still historically have not met my goal. Just this year, I had two external events that provided the kick in the pants I needed to get really committed. I’m pleased to report that currently I am ahead of plan (the real work is staying ahead for me).  Once my commitment was there it has been surprisingly easy (and rewarding) to achieve this, but for years I wasn’t committed enough.

So, I would recommend taking a few small things you want to do and really commit to doing them.  Once you’ve established a pattern of doing what you say you will do, you will find yourself taking bolder actions, and soon you will be well on your way to achieving those dreams!  I wish you well.

In my book, Rebooting Work, I developed a worksheet that may be helpful in connecting your dreams and actions. Here it is: 

Becoming the CEO of Your Own Destiny

Just what does being the CEO of your own destiny look like? It’s different for everyone, but the only way to achieve your goals is to set them.

For some, it can be intimidating to set goals that are both aspirational and achievable. Where do you start?

I’ve come up with a new way, a set of questions that I’ve used personally and that I’ve also shared with the employees of eBay and LiveOps. We start with a game of imagine. (Work with me here):

Picture yourself on stage in front of work colleagues or people whom you admire the most from your industry. You have the opportunity to tell them your story: all of the challenges, all of the accomplishments, all of the choices you’ve made. When you are finished, you get to see their reactions. There are only three choices:

A. They are amazed.

B. They think this is what you should have accomplished.

C. They are unimpressed.

Clearly we know which camp we want them in. But what’s the most likely response? Probably B. That’s OK. It gives us tools to know what we would like to do differently, and the worksheet below will help you get there.

Take some quiet time by yourself to go through these five steps. They will help you determine what getting to “amazed” means to you. And by helping you articulate what you really want, this process will also provide the first step in designing a road map to achieving amazing results.

As you go through this exercise, it’s important to remember that this is your plan and no one else’s. This is a tool intended to help you build a credible and achievable path to your dreams.


Project yourself five years into the future. You are back in that room on stage. Tell your audience where you are in your life. What has your audience in awe? What would you view as wild success?

If you hear “I can’t,” when you try to think about your dreams, take some time off, and write down the impediments that you see.

Realize how much is holding you back. Now, consciously let it go.

Start again. Think about what you want. Dream big. Think about your personal and professional lives synergistically. These are not separate dreams. What is your potential, your life purpose? What does success look like to you?

Now, what does success look like in nine months?

In two years?

In five years?

NOTE: This Aim High step is not easy. If truly done well, this will take some energy and soul searching.  When you take time to really ponder what YOU want to do, it is very likely to be hard and even uncomfortable.  That’s okay.

If you are having difficulty articulating clearly what your “Aim High” goals are, stop and answer the following questions.

  • Does combining personal and career goals cause the problem?  If so, do the worksheet separately for each and then do the consolidated one.
  • Can you articulate “Aim High” goals in your personal life? If not, think about the things that are holding you back from being able to articulate the goals. Write them down. If it is still unclear you may need to seek some outside coaching or counseling. Dedicating time to talk about these issues will help bring some of the answers to light.
  • Can you articulate “Aim High” goals in your professional life?  If not, what questions come into your head that prevent you from achieving clarity? List the questions individually and write down the answers to the best of your ability.  If it is still unclear, you may need to seek help from a mentor.

The most important aspect of the Aim High exercise is to be totally honest in what YOU want to achieve. Don’t get intimidated by the sacrifices required to achieve your ultimate potential. This section of the worksheet is about your aspirations, not your impediments. (We’ll worry about those later.)


What matters most to you in your life? Life is not a single purpose. We all have many roles and we’ve compartmentalized our work and home lives. People have looked at these as separate spheres. I encourage you to look at them holistically. Here’s what most people don’t understand: these dual roles do not have to compete. They can co-exist and work together, even complement one another. Achieving this, however, requires some planning. You can’t have it all with a haphazard approach.

List the different successes that you want to achieve. Be specific. Some examples: ensuring that you are fully available for your children; providing for their college education; being a fully present partner or spouse; achieving economic freedom; having a successful and fulfilling career. The trick here is to recognize what is most important.  Prioritize the list.

NOTE: I want you to dream big, and with the advances we talked about you can achieve more than ever, but you still need to determine what matters most to you. Even if you’ve embraced the spirit of “AND”, AND you want to do it all, you must recognize that you can’t always achieve everything. You must make decisions to determine what’s most important so that you can ultimately achieve your goals.

You must always ask the hard question: What trumps what?

Write down your goals as they come to you.

Take time to prioritize them:

1.     ______________________________________

2.     ______________________________________

3.     ______________________________________

4.     ______________________________________

5.     ______________________________________


Are there examples, role models, and resources available that illuminate how to achieve your goals? Who else is doing what you want to be doing? What can you learn from them?

List the people you are inspired by who can serve as role models (you do not have to know them personally):

Determine how you will figure out their secrets to success, or whatever it is you admire most about them. What will you read about them? Is it possible to engage with them?

Based on what you’ve learned, what have you determined your path should be?


Southwest Airlines CEO Herb Kelleher once said, “We have a strategic plan…It’s called doing things.”  It’s time to do things. It’s time to commit to an action plan—one that you can follow.

List 3-5 things in each of the following categories:

  • What you will START doing (that is new and different)?
  • What you will STOP doing (that is holding you back from your dreams of success)?
  • What you will CONTINUE doing (that you want to take with you on your journey)?

Get feedback from your professional network as well as your personal network (your partner/family/friends) on what you have here.

Take a look at what you’ve written down and determine if your outlined actions, if implemented, will lead to your desired goals. Don’t go forward until they are credible, achievable and aligned. Iterate accordingly. Once everything is aligned, pause and commit to doing each of these items. 


Now that you have gone through this process and have some perspective, go back and think about your Aim High goals. Do they still resonate with you? Has anything changed?

Success builds on success, so checking in frequently on the goals and readjusting them as you progress is important.

Look at this list every week to determine what you should start, stop, and continue.

Reengage in the process every year.

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