When Is It the Right Time To Move On…7×7 Mentors Answer

Social Media Week

Today I’m sharing another edition in the series of posts based on a 7×7 Mentoring Salon I did for SMW. It’s where seven up and coming entrepreneurs pose a question to seven experienced leaders. While the session was focused on entrepreneurism, the issues facing these 20-somethings are similar to those many women today. I am inspired by the honest, open and smart advice these mentors offered up.

Allie Mahler is a social entrepreneur, educator and community builder invested in creating long term sustainable impact in New York City and beyond.


Her question: How did you know it was the right time to move on to the next thing? What were your signals or markers? Would you advise somebody in their twenties to make quick transitions to find out what fits or to be more methodical in their approach to their career?


A. I think people give up on jobs too quickly. There is going to be bullshit in every organization. You can walk through the door thinking one thing and find something totally different. You have to learn how to navigate that. If you want to lead an organization—you have to realize that business plans are not static. The market is an ever-changing landscape. It’s like trying to plot a town but the streets move. It doesn’t always grow the way you think it will. You have to be able to deal with whatever comes at you. You need to stick it out in places for a little while.

I think two years is a minimum to understand the politics of what is going on around you. Then you can make an assessment. Before that you have to realize that people that look at your resume and see 6 months, 8 months, 10 months, a year—and will wonder what will you do by the time I’ve given you enough domain – will you be ready to ready to take on more or will you be ready to leave? Having said that if it is really a bad situation, you want to leave before that point when you just can’t take it anymore. —Justin Stanwix, Director, Friends of eBay


A. If you’re not learning anything anymore, you really should get out because life is about continual learning. —Adam Quinton, Chief Financial Officer at Nopsec


A. I co-founded a fund with Clayton Christensen up at the Harvard Business School that focused on disruptive innovation. One of the things I’ve looked at a lot is this idea of disruptive innovation applied to individuals. I’ve taken the S curve that we usually think about in terms of how quickly an innovation will be adopted in the market and then analyzed it as the psychology of personal disruption. When you’re at the low end of the curve, it takes awhile for a product to gain momentum. Similarly when you start a new job, that first 6 months is just going to be hard.

When you’re in the low end of the curve, it looks like you’re not gaining momentum. But you are and knowing that helps you avoid discouragement. After about six months, you start to accelerate into competence and confidence. Everything is working. Once you get to the top of the curve, you know exactly how to do your job, which is good, but it also means you’re bored. Once you get bored, that plateau can become a precipice and this is the point at which you need to disrupt yourself because if you don’t, someone else will. This helps you to understand that in the first 6 months you might get discouraged. You don’t want to move to a new curve in those early six months when it’s just hard because ….hard is just hard. Millennials, on average, are going to move jobs every year and a half, but six months is too fast. – Whitney Johnson, Speaker and coach, co-founder and managing partner, Springboard Fund


A. The question relates to any transition in your life. There was a point in my career when I realized that all the plans that I created got blown up because life happens. I was frustrated. I started to do what I call now a “strategy screen”. Actually I did it with my partner. It’s a list of questions that we ask ourselves whenever it’s a transition period. It could be anything related to family, friends or career…from “Will this put us on a path to financial freedom?” to “Is this in alignment with my life’s work of advancing women and girls?” or “Will our parents be proud of us?” We go through a list of questions and if the answer to all the questions is “yes,” then we commit to doing it and figuring out the details later.

Sometimes it means really crazy things like..okay you are going to live in Dubai and I’m going to live in New York with a 1-year old and growing a baby in my belly. People ask, “How do you do that?” And I can always say, “It’s in alignment with our strategy screen”. Lo and behold, I look back and—I couldn’t have told you that I would be on the stage today five years ago. I couldn’t have told you that I would’ve led the White House Project. I couldn’t have told you that I would be at Levo League. But I know that I’m on point in my mission of advancing women and girls and creating change in the world. I think it’s important to have something that centers you in that process.– Tiffany Dufu – Chief Leadership Officer to Levo League and Launch Team member to Lean In


 A. That is the difference between a job and a career. You can change your job anytime. What Tiffani is describing is a strategy – a strategy for her life, a strategy for her career. We’re allowed to have different chapters in our careers. The jobs are the simple tactics behind the larger strategies towards our life and towards what we’re trying to accomplish. We have to be accepting and open to the idea that tactics are going to change along all the way based on our criteria. It’s important to think about the difference between the two. A job is not necessarily the same as career. – Taylor Davidson, Director of kbs+ Ventures


A. I think it’s about values as well. I was the CEO of a council of a national organization for about seven years. I was at a barbecue at Tony Hsieh’s house, the CEO of Zappos. When we arrived, we had to fill out a name tag and put our name and our 3 top personal core values. Later on that night, I was talking to Tony and I was talking about how I had been trying to change things at my organization it just wasn’t working. He asked me, “How much do you trust the people leading the national organization?” I answered, “I don’t really trust them that much.” He asked, “How much energy do the people in the organization have?” I answered, “They don’t have much energy.” Then he asked, “How curious are they?” I answered, “They’re not really curious.” He had read my name tag. I realized that he basically just told me the place that I was working was not aligned at all with my three personal core values. I went home and cried.

But it was a big moment for me. I was really engaged and happy with what I was doing locally, but at the bigger picture level, things have become really misaligned with my values. I think there are some markers that people look toward on a day-to-day basis, such as: Do you dread Monday mornings? Do you dread Thursday mornings? Are you constantly justifying to yourself that you should like this job? Or you go through this thought process that you are lucky to have a full time job. Or that you are at an amazing organization. Or that you should like working here. I think that if you’re trying to convince yourself over and over again that you should like something but in your gut you’re feeling like you don’t, that can be a problem.

That being said, I also do think that sometimes it’s not the job. Sometimes it’s the components of the job or the fact that your life as a whole is not the right mix. So if you’re spending all day at your job answering emails and you really need a daily creative outlet, sometimes a job can start feeling awful simply because you’re not doing some of the things that really make you feel fulfilled and make you thrive on a continual basis. So I think it’s important before quitting a job, to assess some of those things. – Jessica Lawrence, Executive Director of NY Tech Meetup


A. I’m going to leave one last thing on the table. Whitney said that on average, millenials will change jobs every year and a half, that’s the average. Don’t be average. The most successful millenials that I know actually have more awareness. They realize that part of making a better decision in the first place is realizing that it’s not enough for a job to sound cool. It’s pausing and thinking, “What does this role really entail? What can I bring into it? What do I need to negotiate to make it work for me? They realize that their values are what stimulates them more than the job itself. It’s may mean going a little slower before leaping into the commitment. It’s not about, “Everyone says this job sounds great.” It’s about saying, “Wait…what is the day-to-day? I think that the other shoe drops most of the time because you didn’t think about it. —Justin Stanwix, Director, Friends of eBay

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