1. Working for free when it matters. While it’s important to set and keep your value as you create it, it’s also important to know when you are more of an apprentice and less of an employee. If you are actively learning something, or breaking into a specific aspect of an industry, it’s likely your best moment to work for free. It can feel counterproductive, and you might have to swallow your pride, but if you do it right, you will be working in your own best interest while creating important connections in your field. But it can’t be indefinite, which brings us to #2:
2. Saying “no” to projects, assignments, and jobs that are not at your needed level of compensation. While at first, you’ll want to take everything that comes your way, and some working for free (or little) can be helpful at the start of your career, at a certain point you have to set your value. And one of the hardest things to do is turn down things that actually interest you on a professional level, or offer a little bit of compensation, when you’d like to take anything. But if you don’t establish your value and keep raising it, it’s going to be very hard to move forward in any professional sense. You’ll either get stuck on the internship treadmill, or you’ll never get the per-job rate you actually deserve.
3. Being rejected. If you are afraid of rejection of any kind, you are almost doomed to fail in your career dreams. No matter what level of success or visibility you reach, and no matter how talented you are at what you do, there will always be doors slammed in your face. There will always be negative performance reviews, or interviewers that don’t call back, or emails that go unanswered. Learning how to shake that off and say “onwards and upwards” — and really mean it — is key to getting anywhere.
4. Working for something you might not get. A further component to the “not fearing rejection” part of things is the “working at something even though it is not guaranteed a payoff” part. For example, I (and Lauren) have worked in advertising in some way or another for the past few years, and a very frequent reality in that industry is that you will work night and day on a pitch, for weeks on end, in addition to massaging the client (lol), and you very well might not get the project. It will all be for nothing, and you just have to deal with that. And this is true in pretty much every professional field, whether you’re going out for lengthy interviews or angling for a promotion. The idea of “work” not always equating to “success” is something you have to get used to, and embracing the work for what it is (and appreciating what you learned from it) is the only way to stay sane.
5. Accepting friends and family who might not “get it.” Yes, the approval of loved ones is always nice to have, but at the end of the day you don’t need it to get what you want. If you are happy and confident in the career path you’ve chosen, and are working actively towards your dreams, having some naysayers around you is just something you have to tune out. And the more “bold” your career dreams are, the more this will be a problem. When Lauren and I left our jobs to pursue TFD full-time, you can bet that a lot of our social circle was doubtful at best. (Less so for me, because I was already coming from an internet-based job that most of them didn’t understand.) But she (and I) learned to not really care about what they said, and realize that their approval is just a bonus on top of the essential — being happy and fulfilled in what you’ve chosen for yourself.
6. Putting your “self-care” on hold temporarily. There are going to be times when things like regular exercise, brow threading (lol), and socializing with friends are all going to fall on the back burner. You will feel like a bridge troll, yes, and it will not be fun. But being ready to ride out these periods of personal not-greatness to get something done that needs to be focused on — like a super-intense project or deadline — is essential to following big career dreams.
7. Saying “I need a break.” On the flip side from 6, though, you also need to know how to say to someone “I need to stop/slow down” and mean it. There are going to be times when your “putting the personal on the back burner” is putting you dangerously close to a burnout, and being able to be honest with an employer/client/yourself and say “I have to take a day to myself this week,” or not work for an entire weekend (not even checking your phone!), that’s hugely important.
8. Negotiating for what’s important. Probably the biggest fear we all have to get over, if we want to really follow our dreams, is negotiating. It literally took me several years into my career to have the confidence to come back against an initial offer, even when objectively it was much less than I was worth at that time. It just felt so scary to me, and part of me felt that the power to negotiate was something that could only be earned over a really long period of time in your career. But ever since I broke that seal and got used to negotiating for myself/my business (out of necessity), I look at pretty much every offer as a starting point. And unless it’s exactly what I wanted, I am always ready to go back (in a polite and thoughtful way). And the truth is that, 80% of the time, I get at least part of what I wanted.
9. Networking. Yes, it feels like bullshit sometimes. And for a lot of people who are really introverted, it can be extremely hard to view socializing as part of the “work” you have to do in your career. But making meaningful connections with people is going to be half the battle, especially when you’re starting in a new field. As long as you treat the connections in a sincere and helpful way — and are ready to take people out to coffees/drinks/lunches for brain-pickings when it’s important — the human side of what you’re doing will end up doing as much lifting as the actual work you put in.
10. Reaching out and following up (intelligently). Imagining that every time you reach out to someone (or follow up, after giving them an appropriate amount of time to respond to something), you are pissing them off, is only holding you back. It does take courage and tact to know when you need to advocate for yourself, and either reach out for the first time or remind someone of something, but crawling back into your inbox and feeling defeated is never going to get what you want. Judge what an appropriate time is for whatever you’re in need of, and once that’s up, politely and calmly follow up. And when you need to reach out to a new person, just say what you need to say in a sincere way, without being kiss-ass or needy. Just be straightforward with them (and never put a misleading or emergency-sounding subject on the email, because that WILL piss them off). The person might be busy, but that doesn’t mean you have to be silent. Just be thoughtful.
11. Walking away. Having the courage to say no to something, and to mean it, doesn’t come easy. But unless you learn how to stick to your convictions and really follow through on them, your word will mean nothing. Sometimes this might mean something as serious as leaving a job, but if you don’t put your own boundaries and stick to them, you’ll be doomed to be walked over your entire career.
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