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Secondhand Therapy

haley rose

Career coach and former startup exec acquired by Big Tech. Weekly essays on career struggles, the job hunt, life observations and all the other hard stuff from someone who usually charges for this kind of advice.

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Substack
PricingOnly free issuesPublishesWeekly
Issues46Founded3 years agoLast Issuea month ago
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Latest Issues

The Most Damaging Question Americans Ask Each Other Every Day

For the new crowd: welcome. This one's from the vault.

After being acquired by a major tech company after years of living the start-up life, there was a catch:

I couldn’t tell anyone.

I couldn’t tell anyone for almost a year — not unti...

a month ago
6

Negotiation Prompts for People Who Are Still Mad About a Salary They Accepted Three Years Ago

A Pre-Read Note:
These prompts work across salary negotiations, raise conversations, scope pushback, deadline extensions, and asking for resources. Not just job offers. If you’re currently employed and thought you could skip this one: yo...

a month ago
1

This Is Why Your Boss Is Frustrated With You

A warning: Before you jump into this critique, understand that this issue is not limited to one generation. While much of what follows is based on what I see in the current "entry-level" landscape, I’ve seen Boomers and Millennials alike st...

a month ago
6
2

How to Handle Resume Gaps: The Guide to Explaining Unemployment

Next week we take a little vacation from career content, and honestly we all deserve it. But until then…


The great American myth, right beside the delusion that waking up at 4:30 AM makes you a morally superior person, is that your...

a month ago
3

Stop Calling It Experience. It's Just Fear.

Millions of years of evolution and we’ve peaked at checking Slack on the toilet.

There’s a very specific thing that happens around year three or five or ten of doing the same job (or career). Maybe it’s sooner for you, maybe it takes longe...

2 months ago
10
2

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  • haley rose

    Former startup exec acquired by Big Tech. Essays and commentary on modern work and the increasingly strange experience of being alive.

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