As I review my next steps, I have many, many, many variables to consider. Above all, I want to take on a role where I can be successful *long term,* not just for a few “burn myself out” projects — OR, take on a role where “burn yourself out” projects are the norm. I’d be much better off in a creative industry working on television shows or movies, but it’s a bit too late for that, especially given my massive fear of change. I’m trying to work with what I’ve got here. And, at the least, I have options. And good ones at that.

Ten years ago at about this time, I was getting fired from a marketing internship at a non-profit. It was my first year out of college and I didn’t know what on earth the future held or what I wanted to do. I applied for hundreds if not thousands of jobs and rejection emails gave me a warm, fuzzy feeling that someone or something out there reviewed my experience, or lack thereof, and decided to personally not give me a chance. Since the full-time job thing wasn’t working, I applied to a pretty-much unpaid reporting internship and, when I found a place to live, found a part-time admin job which was never a good fit for my ADHD self. I survived the entirety of the internship, but the part-time admin gig was, well, a predictable disaster.

Although I moved on and continued to apply for job after job after job, I didn’t know what I wanted in life. I had no friends in the area, very little family, and the only reason to live was to try to make money… to save a little bit… to build something when everything around me was crumbling. I somehow impressed a magazine that I was a worthwhile hire for an editorial assistant role and I stayed for a year, writing articles and attempting to become a better reporter. But my social anxiety really got in the way of that. I did the blogger thing for a short while, which was even worse, because bloggers need to be super aggressive and not let anxiety get in the way of getting a scoop. My journalism career practically ended before it started.

Without rehashing my C.V. for the thousandth time, the point is that I haven’t really massively succeeded in any one role. There have been pieces of roles where people have seen my strengths, and there have been times in the past 10 years where I’ve really poured my heart and soul into projects, and they’ve been considered significant successes. But nothing has ever been sustainable – you can say I just need to suck it up and work, but when you have ADHD and bipolar disorder, it’s not that easy. My mind doesn’t work that way. I have the potential to do great things, or not so great things, but very rarely anything in the middle. I seem to be failing at acceptable.

When it comes to my two or three job opportunities that are getting closer to being real, I consider all of the elements of the role and companies. A few of you long-time readers have warned me that it would be absolutely idiotic to take on a role at a smaller company again. But – there are reasons I failed at those companies that #1, are unique to the companies (not due to their size) and #2, there are similar issues that would happen at a company of any size. If anything, I am more suited for smaller companies because I need to move fast and get things done, or else I get bored and demotivated, and that’s when I do my worst work. If I’m just a cog in a corporate machine, I might keep my job longer just due to HR policies, but I certainly won’t be helping myself or my firm.

The smaller company job is exciting to me right now because I can see many things I can do in a very short amount of time to make a huge difference. I want to compare this opportunity to my past failures at smaller firms to try to hash out the difference, and realistically explore why a smaller company is or isn’t a good idea…

My past two companies, which have ranged in size from 20 to about 100 employees, had significant challenges unique to each opportunity.

Upon leaving a smaller firm where I stayed four years without getting fired(!), I took on an opportunity I knew I wasn’t the right fit for. The head of the company was an expert in my field, and while it’s his fault for hiring me without asking some basic questions to establish if I actually knew what I was doing or what he expected me to do, I also had a boss who had a very set way of how he expected me to get my job done. I really didn’t know what I was doing and it became clear pretty quickly that I wasn’t the right fit. If I were to take on that job now I’d actually do  much better at it. I still wouldn’t be the right person for the position, but I now know enough that I could have lasted longer. I was just clueless and five months in when I was let go, it was the right decision for the business. Given the industry the company was in, I couldn’t even do the things I do best there because of the industry. It was just a very bad fit from the start.

My next job, where I stayed a year (which is respectable in startup time), I picked a company in an industry that I care about. Yet again I found a CEO who was starry eyed about me and recruited me so aggressively I had no time to discuss my strengths and weaknesses. I was thrown into the fire, but at least was given a reasonable budget to work with. But everyone at this company would agree – there are some serious management issues teetering on schizophrenic. Another trend – the head of the company had a background in something similar to my role, so he had a lot of strong opinions on how to do the job, and would basically force me to do a whole bunch of things that didn’t make sense at the expense of time to do the things that had to get done. I did fail to hire a team for a number of reasons, some of which were out of my control – the biggest problem was that the company had a lot of fundamental issues and it still does (lots of people have quit by choice over the last few months and the trend seems to be continuing.) Beyond the basic issues of the core business, the head of the company’s behavior teeters on sexual harassment (anyone working at the firm would agree) and everyone working there is so stressed and upset that they end up taking it out on each other.

Despite the challenges at the company, and it being the right time to leave by choice or by force, I learned a ton in the last year. I worked with an outside agency who taught me a lot about how to do my job. I learned how to not waste money through a bunch of trial and error and how to do things faster. I also discovered a bit about the types of people I like to manage and the types of people who I cannot manage. I learned how important recruiting is and how challenging it is at any company but – it’s actually easier at a hot young company than a big corporation or a startup that has been around for years and is on the verge of falling apart. If you can’t attract the right candidates to your firm, you’re pretty much fucked (or you’re spending a whole lot of time on recruiting that you should be spending on getting your job done.)

Ok, so why even think about going to a smaller company again? Haven’t I learned my lesson!?! Well, as you can see, a lot of the issues had at these companies were company-specific, or addressable by the fact that now I have about two more years of experience and I much better understand the bigger picture. I understand how much things should cost so I’m not freaking out every minute about budget and wasting too much money or not spending enough. I’m not saying I’ll be perfect at my next job, no matter where I go – but I do know I do my best work when I care about the product my company is making and respect the people who are making it.

The smaller company I am considering is SMALL, don’t get me wrong — there will be challenges for sure. But the founders are a bit younger – closer to my age (I think the head of the firm is maybe 2-3 years older than I am) – and this makes a huge difference in team chemistry and respect. I’ve always worked for teams where the execs are in their 40s/50s, and much older than I am. I’m fine being the only woman in a senior leadership role, but it helps with the others aren’t all dudes who are going through their personal mid-life crisis while making the younger women of the company feel uncomfortable.

What’s great about the small company is that I believe in them. I see that their product is already getting a lot of traction, and I see a lot of ways I can quickly help – and I’m super excited to jump in and do just that. I know I have some hiring to do – but I also have the momentum of the company and it’s early stage to help source the right talent. There are really two types of employees in Silicon Valley – the ones that like early stage startups and want to be part of growing something — and then the ones that want to work for a very late-stage startups or public companies that are big and somewhat stable and come with that fancy brand name and cult-like culture. It’s really hard to hire for the middle ground… the companies that are not hot, sexy startups but that haven’t made it… the ones that are dying a slow and painful death, who often have second or third CEOs who are brought in to “save” the company which had about a .00000001% chance of actually saving.

So, in short, not all small firms are created the same AND my experience today is vastly difference than my experience from a year ago. I have a fairly strong opinion on what to do and who to hire, and I won’t be floundering quite as much for the first six months on the job. I’ll certainly hire a detail-oriented person to be on my team, who balances out my big-picture strategy style. And I just think I can knock this one out of the park. If I didn’t, I’d never even consider it. But something tells me this is a really good opportunity. But I could be delusional. I could be lying to myself because it’s the most exciting opportunity, but not actually the best fit. I’m trying to sort that out.

The larger private firm is also a really good option. What I can’t figure out is how much is broken right now and how much is working. It’s not a stable public company and it’s not a small, early-stage company with the fun moments of cherishing each win and feeling part of that with the whole team (I really love that about smaller companies.) My role would be very vital to fixing some of the pieces that aren’t working right now… and I can see what those are and have some ideas how to get things in order… but once I get the basic stuff functioning, I’m not sure where I’d go from there. The role seems a bit more limiting. The company’s product, while useful and needed, is not something I can get super excited about. Maybe that’s a good thing? But I’m an INFP and I really need to feel morally connected to my work. I told myself I’d never work for a company selling to marketers again, and, quite frankly, the two larger opportunities I have are selling to marketers. I’m not sure that’s the right fit for me either. Yes, it may be more stable and it may be closer to home and the salaries may be higher (don’t know that yet) but… if I’m not feeling passionate about the product I’m just going to crash and burn pretty quickly.

There are other jobs out there — but so much of the business technology lacks the human side. I like to have that human piece to spin stories and generate buzz. The smaller firm has so much going for it around the stories I can tell, and that’s what I do best, with the right company and right stories. I think I could help all three companies but I see my value being most at the smaller firm. I think what they’re looking for and what they value is a lot more in line with what I do best — they very much appreciate that I can do all the other stuff, but I do feel like they’re hiring me for the skills I actually have, and will value my ideas and contributions in those areas vs constantly debate me and tell me I’m wrong.

So… I am most enthusiastic about the smaller opportunity, but I’m also not 100% on it. I think that the feedback from my readers warning me to not go to a small company again has merit. I hope the above explanation shows why I’m not just jumping into any smaller firm, and that this one specifically excites me for a lot of good reasons. It will be hard and a lot of work… but I want to feel inspired and work hard. I want to go to work everyday thinking that I feel good about building something great with people who deserve to be winners. Good people who aren’t sociopaths or narcissistic or delusional or suffering from borderline personality disorder. Just people who want to build something great. That’s where I want to be, and that’s why I’m excited about this opportunity, history be damned.