More than ever before, I feel quite split into multiple work personalities. If I’m feeling critical, I might say that I’m avoiding a commitment one way or the other. If I’m feeling generous, I might say that I’m just making sure that we’re not putting all of our eggs in one basket by pursuing all opportunities. Jobs, the economy, clients, customers, trends – they can all be fickle, so it’s hard to say no while opportunities still manage to come my way. It’s that freelance mentality. When you’ve created this life supported by hobbling together various businesses and freelance projects for so long, it’s quite scary to cut the cord and jump all the way in.
But I think about doing it all the time – when I’m riding the train to the office sandwiched a little too closely to people on all sides; when I’m sitting at a meeting during an insecure moment of “what am I doing here?”; when I’m at home on my days off folding laundry and catching up on house work before picking the girls up from school. Taking this part time(ish) job at a startup was supposed to be a move towards simplifying my work life, a break from the hustle of lining up freelance jobs so that I could dedicate the time away from the job to work on our business. At least that was the idea. I still continue to freelance because it gives us a more comfortable cushion, but it also covers camp costs and childcare so that I could go into the office. The irony of that kills me, but isn’t this a common dilemma for many working parents? In the end, the job just added another layer of complexity in my already schizophrenic work life. So now I have 3 jobs, not 2. Funny how that ended up working.
It’s hard to believe that I’ve been commuting to a job for a year now. Some things I knew going in – that the commute can be soul sucking, that childcare would be stressful, and that physically working in an office would be a big transition. The AC situation, let alone sitting 8 hours at a desk, is still hard to get used to (I really don’t like wearing 3 layers and a scarf in the middle of summer). The interaction with people is great, and lately, getting off from work during golden hour as the sun gets ready to set makes me want to linger in the city a little longer before heading into the subway station.
What did surprise me was how challenging work relationships can be, especially in really small teams. It’s often as complex as being in a relationship with your spouse or family and it takes a lot of work to foster good relationships built on mutual respect and trust. Being part of a startup, where the future of pretty much everything that you’re working on is inherently uncertain and risky, can feel like you’re on a ship with no navigational course. The highs and little victories can be exciting, but the low points can be the worst too. Things can turn on a dime when winds shift suddenly and you have to execute fast to stay afloat. We’re at a transitional point right now and the work that I’ve been doing for a better part of a year changed when we turned our focus towards something completely different than when I joined. My job title and role was constantly shifting all year anyway and I’m fairly used to change when it comes to work situations given the nature of freelance, but it did result in anxiety-filled uncertainty. I’m still trying to find my footing in this new iteration of the company. Feelings that I hadn’t experienced in a long time, in the context of work, surface quite frequently – insecurity, frustration, but also all the good stuff of being part of a team. The gender stuff too rears its head even though I try not to allow it. All the emotional extras of having a job and commuting during rush hour that I had sort of forgotten about takes up a lot of mental space – so much so that I don’t really have the mental energy to do much else some days when I get home. On those days I feel pretty unproductive, but simply put, a startup job isn’t the kind of job that you can just punch in and out of, and a part time job isn’t really part time when you’re connected to the office online on days when you’re not there.
So my plan to consolidate my work life so I can dedicate more time to the business isn’t exactly going as I planned – not yet anyway – but not all is always lost when things don’t go as you envision. For now, I’m okay with letting things drift to see which direction they take rather than steering the ship too tightly. Taking on a job was, quite frankly, something that I didn’t think would happen considering freelancing worked for us all those years and I loved being self employed despite all its challenges. But sometimes you need to swallow your fears and personal wants in order to do what’s good for your family, and in our case it was a steady paycheck and better benefits. I can’t say for certain that after a year, it’s the right career choice for the future, but I don’t know what the future is – I’m working at a startup, after all. Success rates are notoriously low and most burn out after a few years. But then again, the same can be said about the food industry. Here we still are 8 years later…
Posted by Jenna | 6 Comments
So this new job of mine officially became A JOB this month, and by all caps, I mean I went on payroll in November. Big stuff around here considering I haven’t been on payroll anywhere in 11 years. And the thing that clinched it? Health insurance.
Obamacare hasn’t worked out well for families like ours – middle class, freelancers, a family of four in NYC. When ACA rolled out this time last year, I largely ignored it because I quickly realized that the health insurance that I had through Freelancers Union, a plan that I had switched over to 4 years ago to save on skyrocketing premiums, was still a better deal than the plans that were on available on the health exchange. Our insurance was far from the best (high deductibles and a frightening out-of-pocket max), but it worked for our healthy family and our premiums were relatively low (“relative” being the key word here since most would still balk at the number). What I didn’t know, however, was that Freelancers Union negotiated a year extension to keep their plans while most of the other trade plans that existed were eliminated because they didn’t comply with ACA. I was blissfully unaware.
During the summer, however, I somehow caught on to the fact that our insurance would end this year and that we’d have to purchase a new plan through the marketplace. So I went and searched around and quickly became despondent at what I was facing; the plans weren’t affordable at all. A letter from our insurance company in October confirmed my fears: an end to our plan and a significant increase in premiums for worse coverage.
I always made a deal with myself that if freelance no longer worked for our family I would go get a job, but a freelance career did end up being the best option for us while the kids were little because we were able to save on nanny/daycare costs while juggling flexible schedules and tag teaming on childcare. If you’ve been reading here for the past 6 years, you know all this. It wasn’t always easy and I feel like we paved our own way in somewhat uncharted waters back then, but it was the best of both worlds in a lot of ways.
But getting back to the deal I made with myself…well, I never really had to make that decision because freelancing went great for so many years – 11 years, in fact. Sure, there were dry spells like every freelancer experiences and it was in these moments of sheer panic that I’d promise to look for a full time job if I couldn’t support the family anymore, but work always managed to come down the pipeline.
The truth is, I was also afraid of looking for a full time job. It was a terrifying thought in a lot of ways. How would I adjust to commuting and working in an office everyday? I LOVED working from home and was lucky as a freelancer to never have to work onsite. The flexibility and freedom meant everything and I fought so hard to build and protect it. Whenever I turned a job offer down in the past – even jobs that I would have considered “dream jobs” – freedom over my time would always win out. I couldn’t justify the huge change in lifestyle, not even for a steady paycheck and benefits.
But sometimes you have to see the writing on the wall and I recognized for the past few years that the industry that I was working in was changing. Technology, media, design – it all moves so fast. We’d be foolish to think that the jobs that we could rely on will always be there. While I did have one of the best years as a consultant this past year, the work that I was doing was shifting – less web and more print. The big web projects that used to be my bread and butter projects were less frequent and harder to come by. Parallel to all this is my complicated relationship with design. I think one of the hardest and truest things you can do in life is to recognize and acknowledge when something has run its course. Maybe that’s leaving on your own terms when you’re still on top. Maybe it’s about letting go when it’s time. Whatever it is, it’s not easy acknowledging when something is over.
So it’s true that The Job sort of just happened. I didn’t decide to look for a full time job, there wasn’t a formal interview and this all came down during one of the most difficult times in my life. But sometimes things just fall into place, you know? And then it all started happening really fast, and I found myself helping to set up health insurance for the company and deciding on a job title for myself. And this is why it feels right. I’m helping to build a company and a product from the ground up and it’s going to be wild ride. I’ll admit that I had a moment of panic when I signed papers the other week. It sort of felt like I was signing my freedom away (though part of the deal is I get to keep some flexibility and only go into the office 3 days a week so I can still run our business and work on some freelance on the side. Look, if you want something you have to ask). When I made a little announcement on Instagram about this new venture, it all felt too real. But I’m ready to step into this new role and I realized that the promise that I always made to myself about finding a job if I couldn’t support my family any longer as a freelancer was only half true. I’m not only doing this for them or the health insurance or a steady paycheck; I’m doing this for me.
Posted by Jenna | 21 Comments
There are days when I think I’m crazy for trying to do too much. I don’t usually get to everything that I’d like to do in any given week (close enough, however) and this is almost always a set up for failure, yet I can’t help myself. Maybe it’s a great quality to have – ambition and drive, blind faith that it will all get done – or maybe it’ll be my greatest downfall. Overcommitment. Crash and burn. I haven’t yet and this fuels the perception that it can always be done, so I push on a little more; pile more things on to the list; say yes to everything.
I will say that even though this has been a year like no other, I did accomplish a goal I set out to do, or at least the start of one. Back when I wrote this post about career change, I didn’t have a plan or vision aside from a sense that for the first time, I could make out a foggy path. Sometimes the universe does orchestrate things to open doors that were previously unknown. Or maybe I was fed up enough with stagnation that I willed things to happen. It could be a little of both.
So in addition to running our business and freelance designing, this part time summer job thing got a little more permanent (though what job is secure these days, right? I’m still a little cautious, I guess). This means that I’ll be spending more time at this job, and less time freelancing while I finally attempt to steer my career into a different direction.
The thoughts that sometimes keep me up at night? That I’m crazy to take all of this on. Managing our business while freelancing often pulls me in different directions because I’m essentially running 2 businesses that consist of multiple clients, customers and accounts, so am I crazy to add a third in the mix? Maybe! But I also don’t want to walk away from an opportunity to create something with a smart team of people. With all the risks involved in an early-stage tech startup, I know that there are no guarantees for anything and the likelihood to crash and burn is high if you pay close attention to statistics. It’s a rollercoaster ride, but one that I apparently want to be on.
So why would I want to join another company when I should probably focus on growing my own business rather than someone else’s? I ask myself this all the time, especially since I had all but made up my mind to do just that earlier on in the year. I can’t say that I know the answer, but sometimes you have to go with a gut feeling and trust that it doesn’t let you down when something else crosses your path that compels you to make a decision. Our business is such that it runs fairly smoothly and we know what to expect every year. What we’re not really doing is growing or expanding and we probably won’t unless I turn more of my attention towards helping to make that happen. I’m fairly sure I will at some point in the future, but for now, this other thing feels right. I don’t know if the events this summer steered me towards this decision because I badly needed a change; it was symbolic of how I viewed life now – before and after my brother. I certainly wasn’t looking for a job that I had to commute to (and indeed, the commute a few times a week is the worst part. Getting dressed for work, on the other hand, doesn’t suck despite the fact that the incubator space we share with other startups is mostly guys in hoodies), but I’m enjoying being part of a team that is sort of like family now. This dynamic is something I haven’t experienced in a while. The next 6 or so months should be interesting. I really have no idea what the picture looks like for the first time in a long time. But that is sort of exciting, is it not?
Posted by Jenna | 8 Comments
Nothing like getting knocked back a few pegs in the last week to remind you that you’re on a long road toward any kind of normalcy. I’m not afraid to admit that I’m feeling totally lost. I’m trying not to hold in so much anger at the world either, but this year has totally knocked the wind out of me and it started months before it culminated in our loss. I don’t really know who I am right now; I don’t even know what identity the business is anymore. We’re barely keeping afloat.
Can I tell you a little story? A few weeks before our trip in early August, the girls and I were doing errands in the neighborhood. As we were walking on the sidewalk down our block, I saw a tiny fuzzy green line on the street close to the curb. I looked closely again and realized that the fuzzy green line was moving and that it was actually a caterpillar. Have you ever seen a caterpillar cross a busy intersection? Because I haven’t! I pointed the caterpillar out to the kids and we watched for a minute as it inched its way across. We kept our eye on him as we crossed the street from the other side of the intersection and was surprised that the caterpillar was still visible to us. Incredibly, we could still see the fuzzy green line move from several dozen feet away. As it inched its tiny body halfway across the street (the caterpillar could crawl faster that you’d think) we saw a car rambling towards us right on the street that the caterpillar was crossing and we squealed, hoping that it wouldn’t get crushed. We held our breath as the car passed the light. Was the caterpillar still alive? Oh wait, there was the tiny green line…and yes! It was still moving! But, oh no! Another car was coming down the street. We held our breath again and when it passed, we waited to see if the caterpillar was still there and we cheered when we saw it moving again.
We couldn’t take the stress anymore after the 4th car had passed, so we crossed the street where the caterpillar was headed and I looked for a twig. At that point the caterpillar had crossed two-thirds of the street by itself, but I just wanted to scoop him up and carry him the rest of the way. I walked off the curb and approached the caterpillar with the twig. After a bit of finessing and a fall from the twig where he curled himself up in a little ball, he climbed and stayed on. I carefully walked toward the sidewalk with the caterpillar on the twig and found a leafy place under a tree on someone’s front yard. We named him “Furbert” and nudged him off the stick and watched him crawl away under the leaves.
As we went about doing our errands that day, the girls would ask me why the caterpillar decided to cross the street. Did he know he was entering a dangerous and hostile environment? Was there something on the other side that he was looking for? Or maybe he was a brave caterpillar just looking for an adventure! I think you may know where this is headed, and as cheesy as it may be to completely spin this story into a “fable” of sorts, I’m totally going there because I’m sure we can all relate to that little caterpillar at certain points in our lives. Because that’s kind of how I’m feeling like my year has been, exposed in the wide open dodging bullets that seemingly come out of nowhere. In my case, I got steam rolled by one of those bullets and I’ve been down for the count, but I’m slowly inching my way to the other side. I wouldn’t mind a little help sometimes. My family could use a dose of luck or good fortune, but I know ultimately this work needs to come from myself. Who knows what the other side looks like? I suppose that’s the beauty and mystery of it all.
Posted by Jenna | 46 Comments
This is my view 2 days a week. You’ve probably seen it on Instagram if you follow me there.
So this office thing…was something that was loosely in the works for a few months now, but still a bit unexpected when it happened. Earlier in the year I’d been contemplating some moves that would potentially be a transition away from what I’ve been doing career-wise for the past 18 years. Nothing that was definitive or that held any answers to what I was going to do with my life, but enough of a shift to feel like I was finally doing something about it after years of feeling stuck.
I’m one of those people who can work perfectly fine at home, so I never thought that I would want to work in an office again. I dislike the commute and I don’t (usually) struggle with some of the issues that some freelancers have expressed can be difficult at times to deal with – namely the isolation and the lack of human interaction. I would have never thought that going to an office a few times a week would have been just the thing that I needed while dealing with my brother’s death, but I showed up 2 days after I got back from California and have been going twice a week since. It provided structure and a routine at a time when I was feeling lost and disconnected from everyone in my life, and it helped with this new anxiety of being around other people. I belonged somewhere, I had somewhere to go, and for the first time in a really long time, made me feel like I was part of a team. Although I’ve been on project teams while freelancing, I’ve been working on my own for such a long time that this was the thing I missed most. All of the newness of working in an office – the indecision of what to wear in the mornings, the commute, the lunches, sitting at a desk again, getting acclimated to excessive office AC – all of it felt fitting. I don’t feel like the same person anymore, and life without my brother is new so maybe this is why this feels right for now.
In a way I’m going back to my tech start up roots, and indeed it does sort of feel like 1999 again as far as the industry is concerned. It’s also nice to be doing something other than design, as well as working in a different industry and this is what I’ve been positioning hard for this year. I still have most of my design clients, however, and this has been the busiest 12 month stretch that I’ve ever had as a freelancer, but I’m letting go of some of the work that I don’t want to do anymore. Also, I’m a workaholic and it’s hard for me to say no, but this also means that certain plans and ideas that I’ve had for the year–personal and for the business–have been pushed aside for now and that is ok. I always seem to carry this weird guilt when I can’t get everything done. Self pressure, unrealistic expectations – whatever it is, it’s nothing new, but I’m also trying to learn from things that have happened this year. I don’t know how long the office thing or this job is going to last – another month, the rest of the year…I don’t know, but I’m just going with it for now. Nothing about this year has been predictable, but sometimes the universe does provide you with what you need. Sometimes.
Posted by Jenna | 14 Comments