Ask Dad.

By: Jen Shoop
"You must decide on your priorities and have the strength to stick with them." - Dad

*My Dad showing me how to use my new beauty kit, Christmas morning, 1988. My older brother looks on.

I will never forget when a Magpie reader approached me at an event and said, “I just have to tell you – I love your dad. I had tears streaming down my cheeks reading what he said.”

I still wish I’d asked her which essay she was talking about, but the only appropriate response was: “I know. He’s the best.”

I am fairly certain, however, she was talking about his advice on gearing up for change with a positive attitude. I’ve had so many readers write to me about this post over the past year. My Dad has always counseled his five children to “keep moving forward,” and I love the vision of that message lapping outward, toward receptive ears beyond our immediate circle.

A week or so ago, a reader wrote and asked for advice on navigating a career change. I had my thoughts on this — but I’ve also been out of “the professional world” as it’s conventionally understood for a long time now (seven years!). I feel better suited at this stage in my life to comment meaningfully, or at least with some level of recent experience, on creative entrepreneurship or writing. So I did what any girl does: I asked my Dad. And it occurred to me that maybe it would better to just let him do the talking anyhow, given how much I have turned to him for sturdy advice in my lifetime.

So, today — a quick “Ask Dad” series in which my father answers some questions on navigating career moves. A quick backstory about the provenance of this post, though, as I find it charmingly illustrative of the kind of person he is: I asked him on Sunday, via email, whether he would be open to answering a couple of career questions for my blog, and he immediately (within five minutes) responded affirmatively. I called him the next day with my list drawn up on my screen, my cursor at the ready, prepared to take dictation. He asked whether I would mind instead sending him the questions so he could reflect on them. This is a signature Dad move: he never cuts a corner or shows up unprepared. If we are sitting down to discuss moving companies, he’s already done his research and prepared a prospectus. If we are getting the family together, there’s usually an agenda to cover. This preparedness has deeply conditioned my view on what it means to respect the time of others, and is also one of the many ways in which his love manifests. For other Dads, it might be stocking the WD-40 (which, incidentally, my Dad also does), but — you get what I’m saying. God, we are lucky to be children, and to be cared for, even as capable adults.

Anyhow — onward, to the main event.

For context, my Dad practiced corporate law for many years, working his way up to partner at a prominent firm before transitioning to in-house counsel for a major technology business. He then led a solo practice before retiring to focus on philanthropy. He is known across his family and friends as a man of few words (all of them elegant and well-considered) — and big heart.

Jen: How did you take “the long view” when navigating your career? 

Dad: In looking for a job, I always looked to see how many people had made their careers at the firm. The two organizations I worked for had low turnover in senior positions. I figured that was a good litmus test.

Jen: What is your best tip for negotiating?

Dad: Let the other side do most of the talking. If there is an impasse, stay silent and let the other person start the conversation.

Jen: How did you know when it was time to leave a job?

Dad: I knew it was time when my business life was seriously interfering with my personal life. As a young partner in a large law firm, it became clear to me that 50-60 hour work weeks were simply not compatible with my personal responsibilities as a husband and father of a young and growing family.

Q: What’s your advice if you’re stuck in a job you hate but don’t have anything lined up yet?

Dad: It is a major mistake to stay in a job you hate. Get out. But be very careful how you leave a job; try not to leave on unfriendly terms since doing so may come back to haunt you.*

Jen: What are your thoughts on workplace friendships?

Dad: This can become difficult if your jobs might put you on a possible collision course. My advice:
be friendly but proceed with professionalism and caution.

Q: How do you ask for a raise?

Dad: It is very difficult to simply go in and ask for a raise unless you feel you have not been treated fairly. It is best to do this at a time when you have made a significant contribution.

Q: How do you prevent work from consuming your entire life and/or identity?

Dad: This is really up to you. You cannot expect your company or your boss to give this a priority. You must decide on your priorities and have the strength to stick with them. I believe that finding the right balance will actually improve your job performance not to mention your own personal happiness.

Q: How do you deal with a bad boss?

Dad: Rule number one for me was to always be around intelligent and good people. If you end up in a toxic environment – and have given the boss a fair chance – it is time to either change positions or


*In my experience, this is exceptionally difficult to do when you are finally moving on from a toxic or unpleasant work environment — you have an axe to grind, and you feel that you finally have the opportunity to air your grievances, or set the record straight, without repercussion. However, I always followed my dad’s advice here, leaving on good terms, with a pleasant outlook and commitment to a smooth transition, even when it required superhuman strength of will to do so. I have never regretted this. You never know where life will lead — and you don’t want to unnecessarily burn a bridge. You may need those connections, or references, later in life. Many of my father’s bits of wisdom here come back to a central theme of exercising will and caution in the workplace. There are some environments that are truly nurturing, where a rising tide lifts all boats, but in general, in my experience (even in the non-profit world), people are looking out for themselves and their own livelihoods, and you, too, must advocate for yourself. No one will ask for a raise, or promotion, or lateral move, for you, and you must be strategic and careful in these undertakings. I have found this admittedly guarded approach very helpful in my career.

+More on my Dad here and here.

+Lessons with my Dad in Colorado. After writing this piece, I told him, “You always seemed so available to us during those summers. It didn’t feel like you did any work.” He said: “Oh, no. I spent half my time on conference calls and in the FedEx office.” Funny how memory works, isn’t it? We sift out the immaterial and focus on the things that really resonate with us. This is encouraging as a mother to young children who often feels split in twenty two directions.

+Aren’t we lucky to be children?

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Shopping Break.

+If you like the look of this Doen dress, you can get the look for less ($118) here.

+Obsessed with the blazers from brand Blaze Milano, especially this spectacular wool plaid. They are super investments, but absolutely gorgeous. J. Crew has a beautiful plaid style for much less.

+This “jelly” cleanser is the latest on my beauty shopping list.

+A perfect table lamp.

+Still a few of these “hammock” sets left. So cute.

+A great chelsea boot option — currently on sale for under $300. I have a pair that is NEARLY identical in black that I wore all last winter, especially when traveling to NYC, because they are sturdy enough to handle any inclement weather (plus gross street debris), and they work with skirts, dresses, or jeans.

+Dudley Stephens, on sale!

+Recently ordered two items for the children — am going to hang onto them possibly for Christmas, or for a special occasion in the months intervening: this Plus Plus learn-the-flags set (!) and this magnetic story maker set. Love the latter for teaching the craft of story-writing early!

+The buckles on these perforated ballet flats make them so interesting/edgy — very Miu Miu, but under $100.

+A bunch of the items my daughter picked from our recent shopping excursion to J. Crew are 40% off, including this adorable denim lady jacket she selected all by herself. This little teddy fleece vest I bought for my son is also included.

+A perfect heavyweight striped breton tee — like the St. James one, but $29.

+Cool velvet kicks.

+Love the classic style of this mirror.

+Clever, Montessori-inspired indoor gym set for littles.

+Such a cool hostess gift.

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4 thoughts on “Ask Dad.

  1. Loved this question and answer session with Dad. I think all of us would have loved a Dad like yours, intelligent with a heart of gold!

  2. It’s amazing that your Father’s advice is basic common sense. However, sometimes, you just need to hear it and have someone say what you have been feeling to move forward. Thank you for sharing.

    1. It’s so true — he has a way of cutting through the noise and getting to the core that you just need to hear.


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