Bullish: How to Recover From Career Stagnation And Plan An Awesome Life

Updated January 2022

Today, we have a letter from someone who feels she’s planning her professional life a little later than would have been ideal.

My position is that it’s never too late to get bullish. If you’re healthy, energetic, and don’t have kids or tens of thousands of dollars in debt, then great, get on it! But who’s that lucky? If you are the exact opposite of that, that’s okay too! We’re going to move forward anyway, even if slowly and irregularly. That’s life. Get a pet snail and use it as a personal mascot. We’ll get there!

Here’s the letter:

Dear Jen,

I’m 28, single, and living at home since graduating with a B.A. in Film and Video Studies five years ago. In high school I liked all subjects and didn’t exert much effort to excel. My attempts to take a STEM route at the University level were thwarted by a lack of preparation, low self-esteem, and free tuition, which I took for granted. After lackluster scores in physics and calculus my advisor told me I was better at the arts and asked if I liked them. If only I’d found your work online then! Watching films and creating shorts with friends – my Film & Video Studies major provided new knowledge and feel-good grades and little else.

Since graduation, I’ve held temporary jobs in retail, customer service, web video production, swim instruction, and most recently a two year stint substitute teaching. I enjoy teaching and many teachers have encouraged me to go back to school for certification. I’ve worked as long as eight months in a classroom and know I am more than capable. Despite the encouragement I am hesitant to buy in. I wonder, “Am I thinking too small?” I’m also wary of doing something I’m relatively good at and losing sight of ambition. Moreover, working at a non-profit this summer has convinced me I want to be making donations to charities, not licking and stuffing envelopes to send to donors.

For almost as long as I’ve pondered going back to school to be a teacher I’ve been considering Boston University’s Late Entry Accelerated Program in Engineering. While super-expensive and rigorous, the program allows students with liberal arts backgrounds to pick up an engineering background in 1-2 years (Phase I) before taking a graduate-level program (Phase II) to finish with a masters in engineering. While definitely harder, more expensive, but potentially more valuable, I am not convinced this is the solution for me, either. Is it the most Bullish? I feel like the old lady who swallowed a fly and is looking for a spider to swallow to catch it, when I should be making the most of a little extra protein.

I have applied to jobs in a wide range of areas over the years but rarely hear back and am consequently available every fall to continue substituting. Networking and creating a portfolio website would help show prospective employers what I am about, but I have trouble connecting the dots on my scattered resume. I cannot articulate what job titles I should seek, even as I know what I like: teaching, working with people, being prepared, writing, showing off, and creating things. Still, I have lots to offer. As an introvert I find myself passionate in whatever work I am given and dedicate my energy to being the best wherever I am.

How can I address my varied work history to find employment now and set my sights on a more specific path for future growth?

Many Thanks In Advance,
Not A Scatterbrain

Dear NAS, I’m more than a little annoyed that your professor suggested “the arts” due to your lagging performance in physics and calculus. Maybe because you’re a girl? A girl who wears cute clothes and stuff?

I am reminded of a scene in the ‘80s classic Just One of the Guys, in which the lead character’s journalism teacher tells her that maybe journalism isn’t for her, and instead she should try modeling. She responds by going undercover as a boy at a rival high school and writing an award-winning exposé. I haven’t seen that movie since I was a child, so I may be misremembering a bit, but even then, that journalism professor pissed my eight year old self quite a bit off.

In any case….


Do you want a “real job”?

I’m not surprised that you apply for jobs and don’t hear back. Not just because this is happening to almost everyone in a terrible economy, but because employers are very wary of those who don’t have a history of “real jobs.”

I was once told by a Navy officer that, although you can join the military up to a fairly late age, those who join past their mid-twenties are responsible for way more than their share of disciplinary problems. Absent some really good reason, there’s just something not quite right – or at least not as amenable to authority – about 28-year-old recruits.

If you’ve been doing temp jobs and freelance work for years, you can convince employers of your skills all day long, but they won’t be convinced of your ability to be an employee. I was told point-blank by the CEO of a small company that my experience running my own internet marketing firm for five years was “perfect” for the position of Director of Marketing, but that he just wasn’t sure I would take orders from him. I assured him I would. I was eventually hired (a story I told in one of the very first Bullish columns, Bullish: How Business is Like Dating.) He was sort of right – it didn’t work out.

If you want a “real job,” you could indeed ramp on by becoming a teacher or going to engineering school. It is unlikely that an employer will hire you full-time based on your scattershot work history and your lack of proof that you can be managed.

If you are not willing to be managed, then becoming a teacher or an engineer might not solve your problems.

I do think that, if you’ve been kind of living on the margins of society, having a real full-time job is a great way to establish a life for yourself, even if you eventually want to start your own business. Many women start businesses in their forties, using savings from their thirties.

(See Bullish: Do You Belong In An Institution?)

80s 90s Vintage Fun


Redeeming lost time

In college, I took a Native American Studies class for which I watched a documentary about alcoholism in Native communities and how it needed to be treated in ways sensitive to those cultures. (For instance, in a culture in which it is never acceptable to deny someone help, you can’t really go accusing family members of “enabling.”)

In any case, a counselor commented that some people were reluctant to go into recovery because they would have to face up to the fact that decades of their lives had been wasted.

(See Bullish Life: Breaking Free From Terrible Situations.)

The counselor’s response was that your time and suffering have not been wasted if you can use them to help others. (And then she set up some kind of peer counseling program.)

Your situation is not so serious. But I tell this story because very little in life is irretrievably wasted; you just have to figure out how to use it. Your degree in film and video studies? Social media has sort of gone full-video. You are a teacher. Could you make videos teaching something to kids? You are thinking about being an engineer. Could you make videos teaching concepts in engineering? A fantastic way to bone up on your physics and calculus is to teach it to others. Could you – I don’t mean to get too cute here, but – could you make videos … teaching engineering … to kids, as you yourself learn engineering?

Of course there are YouTube creators and online course creators and all kinds of content creators out there making money – and one good way to rise to the top is to have knowledge that other people urgently need, and to, you know, be nice about it!

And sometimes when you put cool, amazing stuff out there – repeatedly – cool stuff comes to you. After years of co-hosting an adult spelling bee in a bar and doing nerd-comedy, eventually, I ended up in a pilot for a SciFi Channel show, and consulting on a TV show for PBS. Sometimes people know about you for years before something comes along that you’re right for.

In the meantime, you’ll need a flexible source of income while you work on your next big move. The substitute teaching doesn’t sound like that bad a gig – you like it, you have a free or subsidized place to live, and you don’t have to work every day. All things considered, this is a pretty good setup.

(See Bullish: Launching Your Empire While Your Youthful Mojo is Still Sky-High.)

Celebrate Pride LGBT


Doing your own thing successfully

In Bullish: How to Make a Career Out of the 10,000 Things You Want to Do, I proposed a career model for people who want to do all kinds of things at once:

When I say “the model,” let’s actually visualize it. Instead of a giant mess of random stuff, imagine spokes on a wheel. The thing that pays you the money is the hub of the wheel. Don’t necessarily choose the thing you love the most. The thing you love the most is probably something other people love also, so there are too many people wanting to do it and therefore the laws of supply and demand work against you. Pick something you don’t hate but that other people find difficult, scary, boring, etc. Get so deep into that thing that you learn to love it more.

From that thing proceed all the spokes of the other things you want to do.

So what goes in the middle?

Sometimes there’s a temptation in life to think that what is easy and obvious for us is somehow old and trite. It is not.

Use your skills to help people do something difficult or scary, and they will reward you. Use your skills to help others promote themselves, and they will pay handsomely. Plenty of small business want web commercials – videos that play on their websites, or are clever enough that they might go viral. Don’t try to sell your services to poor, artsy people. Sell them to rich, not-too-cool people – those are the people willing to spend the most to seem cool. (See Bullish: How to Make Money From Being Hip as All Fucking Hell.)


Making the right decision

Regarding obtaining employment in the short term, I think you should keep substitute teaching, and/or figure out a way to sell your services to wealthy people or companies, or to make money as an independent creator.

Figure out how to use your skills to help people conquer their fears or make more money for themselves.

As for the long term? You’ve got plenty of options. In order from easiest to hardest, as far as I can tell:

1)      Get certified and work as a teacher. Then what?

2)      Go to engineering school. Work as an engineer, make pretty good money. Is this enough for the life you want?

3)      Go to engineering school and work for yourself somehow (?), live a gentlewomanly life.

4)      Do your own thing, get rich, make the world better, live a gentlewomanly life.

In a way, I’m a little biased in favor of the engineering plan, since it would make you an expert in a quantitative field, a career strategy I’m always in favor of. (See Bullish: Tech Skills Are Not Optional For Your Career.)

But keep in mind that life is long. There are hybrid approaches. You could become a teacher, get your own place and health benefits and all that good stuff, and then branch out into something else, especially if you actually take summers off.

If you get an engineering degree and don’t like being an engineer, you could be a really cool and inspiring math or science teacher who never tells young women to “try the arts” when they’re struggling with differential equations.

You also wrote one very telling sentence in your letter: “I’m also wary of doing something I’m relatively good at and losing sight of ambition.”

You should indeed worry about this. (See Bullish: Are You Thinking Too Small?)

I am led to understand that, to win at chess, you have to play several moves ahead. Get some paper. Make some bubbles and arrows. From “engineering school”, where do you go? And then where? And then where?

(See Bullish: Extreme Advance Planning for Very Smart Women.)

If you can’t draw your way from an expensive degree, or a full-time teaching position, to where you want to be, then don’t go there.

Or even better yet, start at where you want to be, and work your way back from there. It’s almost like cheating, except that it isn’t – it’s just smart and audacious planning.


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