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How long should I stay in a startup that is a career path I don't intend to pursue?

I recently graduated from college and got a job in a startup. As part of my compensation I got equity that vests over 5 years. Our company has done well and seems to have cornered the market and will continue to do so for the next 5+ years. As a result, many private investors have given funds, and I am fairly confident that if I hold out for 5 years, the equity will be the equivalent of me working 5-6.5 years at my current salary. As a young engineer, this is obviously huge and can return investments in the future.

However, there is trouble in paradise. Currently, I don't feel mentored. While the company has become more mid-sized rather than startup, our team is young.
While young people like myself can learn quickly, it's different from learning from industry experts, and I am personally worried that we lack expertise.
Secondly, I am worried I am taking on an increasing risk the longer I stay. I don't have specialized background for this industry and as a result, I haven't made much of an impression with my boss in the year I have worked for him. More importantly, I think I am most interested in in an industry/area that shares some skills with my current job, but am worried that as specialization sets in, after 2-3 years, I will no longer be a good candidate for job(s) I am looking for. If I continue, I will be forced to specialize in a field I don't necessarily want to pursue, and will be forgoing the time to be able to hone my skills towards the career I am most interested in.

Given this, how long should I stay with company? Should I stay 0 years, 2-3, or perhaps 5 or more? My biggest worry is that if I stay and cash out, I will pay an even bigger price of missed opportunity, or be a bad fit for the industries I want to go into even more. How long can I remain with this company without significantly jeopardizing my career?

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Subject: Career question for you

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Mary Jane’s Answer

Are you able to do consulting or training on the side that would grow your skills in your preferred area? Are there conferences you could attend that would offer continuing education and networking opportunities -- both for your current job and the one you'd prefer to have in the future? Have you explored the salaries in your desired area to make sure it wouldn't make more financial sense to jump ship now? I think you need a mentor in your desired field, so I suggest hitting LinkedIn and reaching out to people for informational interviews.

My biggest worry about what you've shared is that you may not get a glowing recommendation from your current boss if you do decide to leave. As you evaluate your options, you need to continue doing a stellar job, communicating with him effectively, seeking feedback for improvement, and asking about opportunities to grow/learn within the company. Obviously, don't do your job search from your company desk and computer. You want them to miss your contributions when you do leave, not give you a shove in the back on your way out the door because they're happy to see you go.
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Matt’s Answer

John,

First of all I want to say that there is no right or wrong answer to your question. In response, I will share a story from my career.

I got out of college and went to work with a family friend and that startup, within 2 years, went bankrupt. You sound like you are in a better spot, gratitude for what you have clarifies the emotion of fear from decision making.
I then leveraged the relationships I had at that company to get a job with our largest vendor on the East Coast (I grew up in SF Bay Area, moved to Colorado after college). I viewed this as an adventure and that I would return from the NYC area in a couple of years (I have lived here for 20+ years now as I met my wife 6 months after moving here).
I worked my way up in a mid-sized company from individual contributor to Director in about 3 years. It does not sound like the company you are in has this sort of opportunity for you so that is definitely something that you either create for yourself (do side gigs, look for additional training opportunities, or try to create that for yourself inside this company by finding someone who will support you- typically not your boss). After about 4 years here I had an epiphany of an idea, pitched it multiple times at multiple layers of the company (all the way up to the board). I was rejected by everyone in that company and, so, I started seeking outside places to do what I wanted.
I found a small start up with 42 employees, a millionaire CEO/investor, and about 300 customers that matched what I felt was the next logical step in my industry. I left a 6 figure salary, a position, and stability, for the same pay as I had right out of college (not much). But I had the knowledge and the understanding and the belief in myself and the idea that I took the risk.
3 years later I was cashing out options at an IPO, left as SVP of Sales and Product, and had experience of folks much more senior than I, all before 30. Now, I was lucky in many ways but I was also willing to believe in myself and take risks that I believed were not as risky as others viewed them as. And I have leveraged that earlier in my career experience to build a very good career that I am proud of.
If I can say anything to you at all it is this: believe in your ability to overcome any challenge, where you are is exactly where you need to be (and that might be to force you to make a change), and that change is absolutely inevitable.
I would always counsel to try and make it work where you are while always seeking the next. Likely, you already know what you need to do and fear and/or doubt is clouding your impetus to act .
I hope this helps.
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Bradley’s Answer

Sometimes we have to make moves in a career path that we are not wanting to do. This is an opportunity to grow and learn and absorb the things that will make you a better employee for your next role.
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Matthew’s Answer

Hi John, I can understand your predicament. First off you need to know that it's OK to not have it all figured out right now, careers ebb and flow, just like life. It sounds like your struggle right now is that on the surface you're in a good spot - good compensation, seemingly solid company, and an equity plan that could pay off nicely if you stay. On the other hand, it sounds like there isn't much room or resources for personal/career development and growth. My advice here would be to utilize content and the internet to your advantage, subscribe to Youtubers or people on social media that work in areas you are targeting to gain exposure and become more knowledgeable in what you want to eventually focus on. In most industries it is easier to go from a less specialized role to a more specialized one, since you presumably already have a foundational knowledge of that specialty, and with said role you would be zeroing in more on a field/topic you've already become familiar with. I would need to know more specifically what your role is and what your company does, but in my opinion I don't think that staying for the full 5 years would be perceived as something negative when looking for a new role. There are a lot of things you can say in an interview if you are asked why you stayed there as long as you did.

What you need to remember is that there is always money out there waiting to be made, but you can never get back lost time. As a financial advisor, my unique advice would be to focus on saving and investing as much as you can outside of your company - open up a brokerage account and/or a Roth IRA and start making frequent contributions, if you're not comfortable choosing your investments you can seek out a financial advisor that can help you, though investing in a low cost index fund like the SPDR S&P 500 ETF (SPY) wouldn't be a bad place to start. The reason I suggest this is because you will start to feel more financially independent in the sense that you won't feel like your financial well being is tied directly to just the company you work for. Again, you don't need to decide on this today or tomorrow, but for you to get to where you are now I think you have a good head on your shoulders, so trust your instincts too. Who knows, you might stay with them for a little while longer, and if you work hard you might move up within the company and start to really enjoy it. Or you may start to feel like you've gotten everything you can out of your role, which might be a signal to start looking for something more specialized like you mentioned. However, the longer you stay the more you'll feel like you've invested a lot into that company, and you might be more prone to staying for the full 5 years to get your equity vested, even if you aren't enjoying your work very much. You're young, you have a lot of years to make a lot of money, so don't sacrifice your happiness or sense of purpose and remember, you got you! Trust that you know what's in your best interest and try not to overstress yourself. There are many paths available for you to a prosperous, fulfilling career.
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Joseph’s Answer

That's a really tricky one. A lot of startups are now using these equity options to trap young employees. From what I understand about the way these things work, offering these packages means they often get away with lower salaries - is that the case for you? If so, you might not be losing as much as you think to move away. After a year or two in this first role, you've now got some really work experience under your belt, and will likely be able to access roles in your target field more easily, and now you're no longer a fresh graduate, there's a good chance of commanding a higher-than-graduate-level salary to match. That was certainly the case for me after a year in a related-but-different industry to where I wanted to be. I don't know your current situation, but I'd imagine that moving for a salary boost now could, over the next 3-4 years, earn you a good portion as much extra as you'd forfeit in equity.

On the other hand, you've got a good package, and I wouldn't want to talk you into leaving it unless it's the right move for you. If you want to stick it out for your 5 years, I don't think you should be overly worried about specialising yourself out of the area you want to be in. In fact, after 5 years in a position, it would be a great opportunity to say it's time for a career change, and especially as you've said there are shared transferable skills to your target industry, I think interviewers would be happy with the explanation that you tried out that industry for a while, but you've always really wanted to do whatever-it-is and want to change path.
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Clarissa’s Answer

I always believe in giving my best in every circumstance. Even though you may not want to stay on for long term in your current industry, I would like to encourage you to do your best, engage your manager and work closely with him. Create the value you are bringing to the company. At the same time, you may wish to do targetted networking with people in the industry you would like to work in. You can ask your friends who are in the industry to refer you to people you can meet with, or attend some industry based events, or request your University for referral (if you are fresh from school). You may just well network imto the job you wanted to do. All the best!
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Greg’s Answer

John,

Thank you for your question. To throw it back at you, do you want to be unhappy for the next 5 years or go in a direction that doesn't line up with your values? Climate and culture is more important to me than just pay. Not all is lost, as you being a recent graduate, I am assuming you are very marketable, you can use this company to add experience to your resume verses someone coming straight out of college so that is a plus. You can also use this company to diversify your portfolio when applying to you next position. I know your question had a lot of monetary valued notions so I will stick with that theme as I ask you a question. I can see that you are from New Mexico, Is the workplace brick and mortar? If so, you can expand your horizon by looking for remote work online... either freelance or consulting on the side, or start searching for a new job. You will see by a simple Google search the average pay for an Engineer in New Mexico is lower than the average pay for an Engineer online. If you are willing to relocate that opens up so many doors.

I hope this helps.
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