Shhh … Don’t Tell My Boss

Being a “slash-career” person, i.e. writer / speaker / researcher / professor, can mean your “boss” is a tyrant-like type who always has a new demand of you, and never celebrates your accomplishments.

This is the “downside” of the “slash-career”. Ideas come at their own time and their own speed; so it’s hard to schedule and plan. Your community is not all located in one spot (say, a workspace, or even the same city as you), and so you often feel isolated. And then this type of work is such that you have many functions: you have to not only come up with new ideas, but represent those ideas, figure out how to make money from those ideas, do your own R&D for new ideas, and so on. You manage the ebbs and flows of creativity,  output, and monies.

For those of us lucky enough to have such a career, we feel bad complaining because this is the kind of work we wanted, and we’ve worked for. In the last few weeks, several colleagues with slash/careers were sharing their challenges and solutions. In case this could serve you, in your flexible work life and potentially a tyrant-like-boss, some insights from those conversations.

What’s next. Unlike a career in corporate life, there is no person you meet with once a year that does a check in and then helps you to navigate or manage your career. It’s not that the person always got it right, but it ensured some process. When you’re living a slash-career, there’s no person you turn to and ask, “what should I do next”. You get to decide that. Which is hard to do, because you often lack perspective and you also could choose amongst 10 things that can take you in 10 different directions. One thing that can be useful is to take a test. What I’ve generally found with the eneagram, strength finders, or myers-briggs tests, is that they requires you to already be self-aware enough to take the test well. And, then it feeds that back to you with more polish and a bucket by which you can describe yourself to others easier. But if you need help on a development plan, the best test is Realise 2. I like it for several reasons. First, the focus is on strengths and energy, rather than weaknesses. Second, it is actionable. There’s a quadrant called “unrealized strengths”. If you use that box, you can choose jobs/projects/roles that will energize you while you grow (and it can also help you avoid projects that use learned behaviors because that’s stuff you’ve been conditioned to do, but doesn’t truly work for you). Third, it’s measurable. If you retake it 6-12 months later, your test results change if you have worked on stuff e.g. unrealised strengths making it into realized ones.

Milestones must be self-driven. It’s funny to watch my kiddo get a certificate for finishing chess camp, or finishing 5th grade and then 6th grade, and so on. When I was in corporate life, there was lots of milestones, like quarterly reviews, or business plans, or promotions. One friend just got a book deal, another a movie contract, and yet, there’s no public milestone to celebrate. In most cases, you can’t even share it to people online, because people think you’re being all braggy. (You might remember, I wrote about this, in how to support an author.) Without a public expression, it can seem like it didn’t happen or it was insignificant. A former SVP of a tech company just finished a five year journey to become a handbag designer. I’m so inspired by her because she chased her dream of some 30 years late in life, and now is on the other side. And, yet, she tells me about the night of passing her thesis assignment — the accumulation of years of learning. After finding out it was one of the best the professors had ever seen, she went home and cooked dinner for her husband and got a high five from him. There was not enough juice in that, she said.

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It’s why I so appreciated it when a friend, Christine Campbell, created a book salon for my Harvard-published 2nd book. She invited her best customers of Crimson Mim to learn about it.  Long before Fast Company named it as one of the best business books of 2012, and it changed the lexicon in business… we celebrated the milestone of crossing the finish line. We had cupcakes, and a nice dinner afterwards.

Through this, it marked the milestone, it created a moment.

And, breaks need to be managed. There are times, you just gotta hide from “the boss”. In my case, I actually ask my husband to take away all my electronic devices. I ask him this months in advance but the night before we leave, you can typically find me pleading with him to let me take the computer because xyz just *has* to get finished. (I know, I know, I got my own issues…) But only when I’m without the phone and twitter, and all that…. that’s the only way I actually feel able to disconnect from my commitments. Another friend gives themselves permission to go somewhere on the next sunny day. They work every day, super hard, knowing that tomorrow they might not. It works for him. I’ve learned over the years that it’s perfectly fine if I turn on autoreplies and just let things pile up until I get back. Why? Because honestly… barely anyone even notices my absence. And whatever productivity I give up, I always get it back when I return. The only person who can show up with this self-discipline is you.

Which explains why this is the essay, this week. I was in windy-but-not-sunny-this-week Corsica with the family and kiddo’s friend.


Home of Christopher Columbus, and 80% of all the violent crime in all of France. Oh, and the fifth rank best whiskey in the world. So I learned a few things, too. 😉


Do you have a slash/career, too? BlogIcon_Right copy

This Corsica break, I managed to convince my husband to let me bring my computer, and then afterwards judged him terribly for not taking my tech away. What do you do to do manage your slash/career?

3 Replies

  1. Nice article again Nilofer! I have been in a slash career for over 20 years. I get my rewards from my coaching clients and training classes in positive feedback. This makes me feel good about myself and what I do . The downside is that when I have not had a lot of work to do with others I can become very self critical and can forget that I am the same person who received all those kudos. I dislike being dependent on the good opinion of others so I try to just be my own cheer leader while also seeking some objective feedback from trusted friends and clients on how to improve. I would also like to say that working inside most companies today looks so much more difficult to me because they have so little control over their time, their tasks and their managers that I am very grateful not to be inside a company because so few people are able to balance their lives. It seems to me that people’s lives are being swallowed whole by what it takes to do a job inside a company today. The great luxury today is time. In this respect I feel rich and fortunate. Life is full of trade off’s. My song is “Freedom” so I am right where I need to be.

  2. For me, developing a community of fellow slash/career’ers has been critical to keeping going. Having a set of people who understand the issues one is facing and can sympathize means a lot when one is feeling the pressure to give up the slash and pick a set of hoops to jump through. It is hard to keep oneself going without the external reinforcement that the hoop jumpers get, so having people who empower and celebrate you makes a big difference.

    1. Eric, ah what a great term in hoop-jumpers, just what Wendy Zito was characterizing, too.

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