Navigate career pivots, changes, and how to know when it’s time to move on
4 reader questions on moving on, differences between Big Tech vs Entrepreneurship, taking a career break to pursue an Executive MBA, and career paths for older professionals
Ethan & Jason here—welcome to a *paid member-only* edition of Level Up: Your source for executive insights, high performance habits, and specific career growth actions.
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I left my prestigious, well-paid Amazon VP role to start my own company at the age of 50.
Why?
Today’s newsletter is about contemplating big changes in your career. When to make them, how to think through them, and ultimately, what you can do to navigate them. The specific scenarios I talk about come from questions our Level Up Community Members have had about their own careers.
In my career, the biggest change that I made was stepping away from Amazon to start my own business. That business is what has me coaching, teaching, and writing career advice to you all today.
The reason I made this decision was because I had found a mission that I wanted to pursue more fully, not just on the side of a busy executive schedule. I wanted to pay forward my good fortune by helping others find career success and satisfaction. Taking the step to leave Amazon and start my business required a few years of knowing exactly what I wanted and securing my skills and finances to do so. I chose the path I wanted, mitigated the risks, and then dove in.
The advice I give in response to the four reader questions follows a similar pattern: Decide, build the support system you need, and make the change.
Here are the 4 questions our community members asked:
“How do I know when it’s time to move on?” — Director, Tech
“What are the most unexpected differences between leading at a tech company and running your own?” — Regional Manager, Special Projects
“How do I take a career break from Amazon while pursuing an Executive MBA and remain competitive and relevant to re-enter the workplace at the next level?” — Senior Leader, Amazon
“What kind of career path is possible for a 52-year-old?” — Solution Architect
If you have a question for me, submit it in the form at the end of this article—I look forward to reading through them.
Also at the end of this article are 3 community member exclusive video recordings where I answered the most popular questions voted by members (e.g. building executive presence, IC vs people management, breaking through the glass ceiling as a 40+ year old woman in a minority group, how to stand out in an executive interview loop, how to get noticed by recruiters, what to do when you report to a peer, what it would have taken me to get to Amazon SVP, how to influence the values of the company, non-engineering leadership roles in tech, how to handle peer conflict, networking strategies, how to deliver bad news to a VP+ audience, etc) and a talk on how to do good while doing well.
1. “How do I know when it’s time to move on?” — Director, Tech
First, I want to acknowledge that I'm asked this question all the time, which goes to show how common of a position this is to be in. People often feel unsatisfied where they are, but they can see the effort and risk required in finding and accepting a new role. So, the real question they are asking is: “Is it worth it? Am I better off just staying?”
My first response to this question is always the easiest one- If you have a better option somewhere else, take it. This may mean that you have an offer at a different company or a networking connection that you can start to leverage. The reason for this is that unless you're in pain or distress, it is better to have an imperfect job than no job at all.
My second response to this question is the more complex one- How do you know it is time to look for that “better option?” For the most part, finding alternatives requires initiating a process. So, how do you know when to start?
The answer is when you are no longer growing in your current position. There are generally two kinds of growth, and every role should give you at least one: Skill growth and scope growth. I have also heard these referred to as “learning” and “earning.” If you aren’t experiencing either and don't see a chance for either, it is time to look for alternatives.
If you're currently getting scope growth, you're probably getting what you want- the path to titles and compensation. If you're getting skill growth, then you are improving and getting skills that can later translate into scope growth. In either case, if you are actively growing in one of these areas, it is worth staying.
Possibly the best reason to move on is if you have a bad boss. If you lose your boss, if your boss is not supportive, if your boss doesn't have the skills, if your boss lacks ambition, etc. Basically, if your management chain is not supportive of your growth, then you need to get out of that role. Your direct manager and your management chain have the biggest direct impact on your career growth, so you do not want to be somewhere where that impact will be negative.
Finally, another reason to move on is that your company is not growing. If it's a stagnant or low-growth company, it’s going to be a really hard situation in which to find the types of growth I mentioned above. So, it's time to move on.
The broad question to ask yourself when deciding whether or not it is time to move on is “Am I getting what I need?” When your own company is not delivering the career growth, the skill growth, the internal support, the good management, or the opportunity that will help you keep momentum in your career, then you want to find somewhere else that will.
But, as a word of caution, go back to the first part of this response. Don’t leave your job until you have something else lined up, unless you really need to. Take time to build your network and get referrals until you can find that better job.
The single best rule here is: “Do not run from something; run to something.”
So when you ask, “How do I know it's time to move on?” The next question should be, “What am I running towards?” If there isn’t yet an answer, the question should be, “How do I conduct my search to find it?”
2. “What are the most unexpected differences between leading at a tech company and running your own?” — Regional Manager, Special Projects
Well, first, I'm going to be honest and say this is not necessarily my expertise. I run my own small company, but there are likely many other differences when someone is running a larger or more complex business.
However, the big difference between running your own business and leading in a tech company (or any company) is that in someone else’s company you are executing someone else's vision. In your own company, you're 100% responsible for figuring everything out, from the vision to the execution. You have to figure out the product, the marketing, the pricing, the infrastructure, the billing, the taxes, the staffing, and on and on and on.
When you're leading at a tech company, you're generally delivering a project. You may have come up with part of the vision for that project, but you're not normally doing every single part of it, from the finance to the legal to the marketing. And, as part of a tech company, you are almost certainly not doing the fundraising. Essentially, even being a leader at a large company is inherently narrower in scope.
Now, it can be a bigger platform or a harder problem. You may be running a much bigger total business as part of a large tech company than you would as the founder of your own business. For example, I was in charge of a lot more money at Amazon than I am now with my business, but I had a much narrower diversity of things I was responsible for.
The second major difference comes down to freedom and responsibility. In a tech company, you have a boss. Maybe it is a VP, an SVP, the CEO, or the shareholders, but it means that you have both limited freedom and responsibility. You have people above you, and the buck doesn't stop with you. There are people you can consult when you need them, and also people that you may have to consult for the largest decisions.
When you run your own company, you have total freedom of what that company does. But, that freedom comes with total responsibility for whether or not the company survives. Some people thrive on that level of freedom, and some people are paralyzed by it, but many people oscillate between the two- They love the freedom, but they're also anxious and worried all the time about the future of their company.
So, conversely, in a tech company, you have fewer freedoms but usually also fewer worries. Google or Amazon isn't going to run out of money, so you have a different type of freedom: freedom to focus only on the technical work, only on the execution work, and not on all those other things that a business owner has to think about.
3. “How do I take a career break from Amazon while pursuing an Executive MBA and remain competitive and relevant to re-enter the workplace at the next level?” — Senior Leader, Amazon
Well, my first answer is that you want several things at once, and you may not be able to get them all. In other words, you're asking, “How can I have my cake and eat it too and have ice cream on the side?” There is nothing wrong with wanting all of this, but it is important to recognize the challenges it will present.