Where to Turn for Career Advice

For people who stay in their family business, or follow in the footsteps of their parents, there’s a common ground for sharing professional wisdom and advice. That’s not to say all advice is good or accurate, it’s just that within the family one can talk about certain professional matters that might not be appropriate to bring up with a friend or mentor. For instance, say you are working for a startup where, like many startups, things are looking good one day and less good the next. Beyond the company potential, as things shift, it isn’t clear your role is right for you anymore. There are so many variables going into this story, and you want someone wiser and older to discuss this with in determining what to do next and when…

There are many people in Silicon Valley who grew up with parents who worked in technology, or who are venture capitalists, or heck, who are both. I bring up the concept of startups to my father and he says “go get rich,” though he doesn’t really think it’s possible. His advice years ago would be to join a big company, now he’s just impressed that I have managed to maintain employment. But who do I turn to for advice? Who can I tell the entire story to and at least discuss the options outside of my own head with some valuable feedback? Eh, no one.

It’s never a black or white decision either. It’s not “do I stay or do I go?” It’s – how long do I stay? Should I ask for more money? Should I get another job offer so I can try to get more money? Should I ask for more stock? Am I underpaid? Heck, am I overpaid? If I do leave, what type of job should I do? Should I go to another startup? How about a large company? Do you think the startup I might go to has potential? What offer should I not refuse? If any? If I do stay, what projects should I take on to grow in my own career? At what point do the signs point to I should leave right now? Will they ever? What is typical mid-stage startup turbulence versus the engine starting to fail? Should I big more outspoken about ideas with the executive team? Should I stay quiet and just keep my head down? When is the right time to speak up? Should I be concerned that people are leaving the company? Are they leaving because they aren’t being paid as “well” as I am in terms of salary or stock? How about getting an MBA? Will that help at all?

Sure, even if I did have a close family member in tech I wouldn’t have ALL the answers, but I’d at least have someone to talk to about all this. But instead I’m left with blogging anonymously and no one to run these ideas by. My career counselor that I hired a few years ago told me to take a very entry-level job at a large tech company versus the startup gig I opted for – had I taken that job I probably would still be making $70k and in the same or a similar role vs now at least having opened doors for bigger and better positions, not to mention a better salary. All I want is some good, seasoned advice from someone who I can confidentially offer up all the data – how my company is doing. How I’m doing. What I’m scared of. Why I should stop being such a damn fickle millennial and just deal with transition and come out on the other end of it all the stronger – right?

I don’t know… I’d like to find some sort of advice… but from whom?




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4 thoughts on “Where to Turn for Career Advice”

  1. I’ve always thought that people who can turn to their parents for career advice were very lucky. My husband and I come from similar backgrounds and are both trying to make it in worlds our parents never knew. I typically turn to him as my sounding board, but I mostly trust my own perceptions and my gut. Friends too, but less so.

    A really great mentor would be perfect, but I think it is rare to find that kind of relationship with someone who has time to really understand the path you want. :/

    Sorry, no good advice here, but I sympathize and hope you find someone to talk with.

  2. Hi. Thanks for writing this blog. My life is very different from yours, but also surprisingly similar. Hearing your experiences in life helps me go on with my own.

  3. HECC,
    Don’t bet on getting appropriate advice from family when in a family business. Advice of that kind is often geared towards supporting/defending the business, not necessarily in the best interests of the person asking for advice. (Trust me, I know…)

    I’d older now, and live in the East Bay, not that far from where you are. Have worked in startups in SF and in the East Bay, as well as some not-so-startup companies. The best advice-giving people I have encountered are former co-workers. Particularly former managers. That is, if I have a good trusting relationship with them. Of course not everyone fits the bill. But I’d say there are at least three former managers of mine who I keep in touch with who would be good sounding boards. (They also volunteered to be references when I apply for jobs.)
    Good luck. [Sorry to say this, but….] try not to obsess…

  4. My family and friends are all in different fields, so I can empathise. My current boss is, I feel, the most likely candidate for this kind of thing out of all the people I’ve met in my industry so far, though I’m not sure it’s totally appropriate at this stage. My husband meanwhile faces it even worse as he really has zero career role models, coming from a culture of welfare/underemployment, and I’m not really up with the play when it comes to his kind of more trade/blue collar industry as I’m firmly in the white collar world.

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