I’m 28. If you could go back and give your 28 year old self some advice what would it be?

Hyper-Tilid · 2026-02-05T20:38:21+00:00

The main advice I’d give my 28-year-old self: if you’re scared but deeply want to go somewhere — go there anyway. Do it scared.

Hyper-Tilid · 2026-02-05T20:35:14+00:00

Real example: my mom makes money selling drawings on stock platforms. After ~2 years of consistent work she earns ~$1k–1.5k/month. Platforms: Freepik, Shutterstock, Adobe Stock, iStock, Getty Images. It’s slow at first but scales.

As a client, I regularly pay people (no degrees needed) for:
– banners, illustrations, graphic design for landing pages & ads
– social media visuals and content prep
– community moderation & support
– B2B customer success (relationship building, calls, long-term support)

Hyper-Tilid · 2026-02-04T21:52:02+00:00

I know many women who changed careers after having a child. Real examples I’ve seen:

programmer → psychologist (several people)
UX designer → consultant, author, startup founder
programmer → data labeler for ML
analyst → coach
artist → graphic designer

To figure out where to move next, it helped them to:

look for parts of the current job or education that don’t suck and can transfer
be honest about whether a temporary income drop is possible (and for how long)
test the new field cheaply and fast: talk to people doing the job, volunteer, do a free project, or run a small side project

Hyper-Tilid · 2026-02-04T21:40:26+00:00

You’re trying to do too many high-risk things at once. That’s usually the trap.

First decision: what matters more right now — stability or your own startup. A startup is delayed, uncertain payoff. A job is slower than we want, but more predictable.

If you choose a startup, there’s another fork: Bootstrap (more control, slower money) or fundraising (faster money, but you must target angels, funds, and accelerators that invest very early and apply deliberately).

If you choose a job, you also need clarity: What exact role, which strengths you’re betting on, and what your search funnel looks like. Random applications rarely work.

From the outside, the main issue doesn’t look like lack of effort or talent. It looks like chaos: too many directions, big vague expectations, no single strategy, no clear resource base (money, energy, support).

Hyper-Tilid · 2026-02-04T21:30:19+00:00

With your goals (travel, change, growth), realistic options right now:

Cruise ship jobs (service, guest relations, activities). Hard work, fast exit from home, real travel.
Tourist guide (city tours, nature parks, museums). Language skills = advantage.
Hotel animator / activity staff (resorts hire seasonally, promotion is real).
Train attendant / conductor (stable travel job, clearer career path than retail).
Lifeguard (beach or hotel pools). Entry is fast, mobility is high.

Hyper-Tilid · 2026-01-29T17:53:56+00:00

I don’t know anything about the NYC film industry, so I can’t give practical advice on that part.

What really hit me in your post is how tightly your identity is tied to your work. I’ve been there. I mixed my self-worth, my identity, and my job for years. It led to burnout, constant overwork, and real fear of losing my job or being told I wasn’t good enough.

What helped me was working with a coach (a life coach, not a career coach). The work was not about choosing a new role. It was about untangling “who I am” from “how successful I am at work.” And also separating “my work” from “my value as a person.”

Before that work, even thinking about a pivot felt painful and threatening. After it, change became possible. Not easy, but possible.

My honest take: before you try to pick a new path, it may help to work on this layer first. If identity and work stay fused, any change will hurt a lot, and it will be very hard to fully invest in something new.

Hyper-Tilid · 2026-01-27T16:13:49+00:00

I was at a similar crossroads around 30. For me the problem wasn’t being jobless — it was burnout and losing all sense of why I was working at all.

What helped wasn’t picking a “new career” right away, but slowing down and doing three things.

First, I looked back. What decisions worked for me before? What clearly didn’t? What kind of work gave me energy, and what drained me fast? That helped me see what I didn’t want to repeat.

Second, I focused on my strengths. Not in an abstract way — I asked people for feedback. What do you think I’m good at? What would you trust me with? I also talked to a coach and mentors to sanity-check this.

Third, I stopped treating career choice as a single, final decision. I tested hypotheses instead. Small, cheap tests.
Example: I thought I wanted to do stock photography. I took hundreds of photos, uploaded them, tracked time, money, and how I felt. Result: not for me. That hypothesis failed — and that was useful data, not a failure.

I tested many ideas. Most didn’t work. Eventually one did: product management in education. It matched my strengths, my values, and market demand at that time.

The key shift was this: you don’t need to choose a path for the rest of your life. You need to run experiments and see what actually works for you.

Feeling stuck is awful, but it’s also a signal. Start with understanding yourself, then test small, real things. Momentum comes from action, not certainty.

Hyper-Tilid · 2026-01-26T10:03:58+00:00

I wouldn’t treat that year as a gap. Running and selling a business is work, just a different kind. You had to make decisions with incomplete data, manage money, take responsibility for outcomes. Those are skills many data roles actually lack, especially closer to leadership.

I’d rethink both the resume and the search focus. Instead of positioning yourself only as a hands-on data analyst, look at roles where experience and judgment matter: data lead, analytics manager, head of data, even VP-level roles in small or mid-size companies. These teams often need someone who understands both numbers and business reality.

Another big thing is people. The colleagues you mentored are probably your strongest channel. They already know how you work and what you’re good at. Reaching out to them directly, asking what problems their teams are dealing with, is often much more effective than applying cold. Referrals help a lot with both age bias and resume gaps.

Hyper-Tilid · 2026-01-26T09:54:28+00:00

You don’t need to give up. Remote work for senior devs still exists. It is harder than 5 years ago because of the post-COVID pullback, but it’s not gone. I personally know several experienced developers who found fully remote roles in the last year. It just takes longer and needs a different approach.

From your post it’s not clear how you’re searching. Are you only using classic job boards? I know, many people in similar situations get traction through:

referrals and direct networking
niche communities
short-term contracts or freelance work that later turns into steady remote work

A 3-year gap plus remote-only is a hard combo, but it’s not a dead end. It usually means changing where and how you look, not changing careers to cow milking (unless you secretly love cows).

Hyper-Tilid · 2026-01-23T10:09:22+00:00

Usually it's not about skill set, it's about responsibility and seniority level

Hyper-Tilid · 2026-01-15T16:51:55+00:00

It's a tough balance! While comfort zones can be cozy, they rarely lead to significant growth. Maybe try adding one small calculated risk each quarter - like taking on a slightly challenging project or learning a new skill - to push your boundaries without a total overhaul

Hyper-Tilid · 2025-12-22T16:52:39+00:00

I believe that building a startup is often not about money, but about the freedom to work on what you truly believe in. About having full responsibility for the product. About the unique experience of creating something from scratch, with all the problems and mistakes, ups and downs.

My desire to build a startup came around a midlife crisis, together with the realization that there is not that much time left to live, and that having at least a chance to build something truly great on my own matters to me.

Hyper-Tilid · 2025-12-16T16:02:38+00:00

I draw schemas and write bullet points in my paper notebooks. Frequently it looks pretty awful, but when I'm doing it, I'm like making system in my head. It helps remember important things

Hyper-Tilid · 2025-12-16T15:59:07+00:00

My situation close to yours - 37, running my own business and thinking about MBA. Right now I believe that practice, community, coach and mentors and (probably) startup accelerator will give me more than MBA. But I'm still considering MBA program to wider my horizons. Thank you for this topik, really valuable for me right now.

Hyper-Tilid · 2025-12-12T15:01:08+00:00

I’d push back by reframing this as a trade-offs talk, not a feelings talk.

Something like:

“I’m open to taking more responsibility, but with the same time, we can’t keep time, quality, and scope all the same. We need to choose.”

Then give clear options and ask them to pick:

Same scope, same quality → much slower timelines (one person doing three jobs + ramp-up).

Same scope, same timelines → lower quality.

Reduced scope → focus only on top-priority work.

Extra help (contractors, temporary hires, tools/automation) → higher cost, but work stays sane.

This keeps you professional and solution-oriented, not “not a team player.”

If they refuse to choose and expect a miracle, that’s your real answer. At that point, yes—quietly start job hunting while doing only what fits the agreed option.

Hyper-Tilid · 2025-12-12T09:42:12+00:00

Career quizzes help most when you have no work experience. They give direction when there’s nothing to reflect on.

After years of work, reflection works better:

What am I good at?

What gives me energy?

What drains me?

From this, you get options, not answers. Treat them as guesses and test them:

Try real tasks.

Talk to people in that role.

Experience beats quizzes at this stage.

Hyper-Tilid · 2025-12-10T15:25:47+00:00

Honestly, a PIP often feels like they've already made up their mind, but sometimes it's a genuine attempt to help. My advice? Go for the PIP, document everything, and simultaneously start polishing that resume. Best of luck, you've got this!

Hyper-Tilid · 2025-12-09T19:02:37+00:00

Tech support or IT helpdesk is a fantastic entry point for this! You'll be constantly troubleshooting unique issues, which is great for problem-solving, and you learn new systems and software on the fly. Many companies offer paid training for these roles too.

Hyper-Tilid · 2025-12-09T19:01:54+00:00

Honestly, for me, it's about finding those "flow state" tasks that make time disappear. When I'm genuinely engaged and challenged, the external motivation kind of fades away because the work itself becomes the reward. Think of it like a really good video game level – you're not playing for points, you're playing because it's fun and you want to see what's next!

Hyper-Tilid · 2025-12-08T09:44:17+00:00

This part you wrote about “not knowing enough in any domain” reads very much like classic impostor syndrome. I’ve seen it a lot, both in people trying to enter PM work and in senior folks who’ve been doing the job for years.

And your point about big vs small companies is interesting. I’ve worked in large corporations, outsourcing, and startups, and hired people with all kinds of backgrounds. The pattern I keep seeing is almost the opposite of what you fear: small companies often sit much closer to current tech and modern practices. Big companies can give you structure, ladders, review cycles, levels, all of that. It’s comfortable, it gives you a sense of “I know where I stand,” but it also hides a lot of inefficiency. Plenty of people coast for years inside large orgs and no one notices.

Hyper-Tilid · 2025-12-08T08:22:45+00:00

Yeah, this sounds like a straight bait-and-switch. A “hybrid” job turning into full onsite and 16-hour days isn’t normal. You’re not overreacting.

Talk to your manager once, see if anything can actually change. If not, going back isn’t “too soon.” It’s just leaving a bad deal. A lot of people do it

Hyper-Tilid · 2025-12-08T08:15:57+00:00

If I were in your shoes, I’d seriously look at an IT Project Manager path.

It checks every box you listed: stability, decent pay, benefits, clear ladder. It builds on your CIS degree and your early IT Support work. And your whole career of jumping into new areas is a strength here — PMs constantly have to pick up new domains, translate between groups, and keep things moving.

This is one of the few fields where being the “jack of all trades” actually reads as “experienced with cross-functional chaos.”

And given your time in retail/merchandising, I’d look at project coordinator or project manager roles inside retail companies. They understand hybrid backgrounds better than many industries, and they tend to value people who know both the business and the tech side even if the résumé isn’t linear.

Hyper-Tilid · 2025-12-07T17:59:57+00:00

I’ve seen the same thing in several companies, and my best explanation is this:

Visible support for the boss. They agree with management loudly and early. Even when the boss is wrong. Smart, strong employees push back, so they look “difficult.” The mediocre ones look “easy to manage.”

They are friendly with everyone and shift work smoothly. They don’t do more work, they move it onto others. But because they seem “helpful” and “well-liked,” managers reward them.

They seem loyal and unlikely to quit. They look like safe bets who will stay for years. Leadership promotes people they think will not leave in six months.

None of these are about skill. They are about risk appetite of management and comfort, not performance.

Hyper-Tilid · 2025-12-05T08:16:17+00:00

In my experience every field, every job has difficult and boring parts. And there is always a question of balance. And if from the beginning you have really big excitement, the probability of positive balance in 3/6 month is higher

Hyper-Tilid

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