From the moment Yaakov uttered the words "Anochi Eisav bechorecha" I think he was faced with an identity crisis. The challenge to Yaakov was to remain the "ish tam yosheiv ohalim," yet at the same time step into the shoes of Eisav for the sake of taking the bechora, for the sake of taking the brachos of הֵ֣ן גְּבִ֞יר שַׂמְתִּ֥יו לָךְ֙ וְאֶת־כׇּל־אֶחָ֗יו נָתַ֤תִּי לוֹ֙ לַעֲבָדִ֔ים, which does not sound like something a yosheiv ohalim needs, and for the sake of taking not just Rachel as a wife, but Leah as well. As we read last week עֵינֵ֥י לֵאָ֖ה רַכּ֑וֹת because, as Rashi explains, לפי שהיתה בוכה, שהיתה סבורה לעלות בגורלו של עשו. שהיו הכל אומרים: שני בנים לרבקה ושתי בנות ללבן, גדולה לגדול וקטנה לקטן. This destiny was in fact fulfilled, because the katan, Yaakov, had usurped the role of Eisav in addition to his own role, and stood in his place.
The Bas Ayin interprets the battle of Yaakov with the angel, the sar of Eisav, represents Yaakov's struggle to remain true to the midah of anavah, humility. וַיֵּאָבֵ֥ק אִישׁ֙ עִמּ֔וֹ means Yaakov struggled to avoid thinking of himself as an אִישׁ֙, as a gavra, as someone of importance. וַיִּירָ֧א יַעֲקֹ֛ב מְאֹ֖ד What Yaakov was afraid of, explains the Bas Ayin, is losing his midah of מאד מאד הוי שׁפל רוח. I think this is the same struggle I described above, the struggle of Yaakov to maintain his own identity as the ish tam. וְרַ֖ב יַעֲבֹ֥ד צָעִֽיר only works to Yaakov's benefit so long as he remains true to his identity as the צָעִֽיר and does not get swallowed up and become the רַ֖ב.
In light of this, the crucial words in Yaakov's tefilah at the beginning of the parsha are קָטֹ֜נְתִּי מִכֹּ֤ל הַחֲסָדִים֙ וּמִכׇּל־הָ֣אֱמֶ֔ת אֲשֶׁ֥ר עָשִׂ֖יתָ אֶת־עַבְדֶּ֑ךָ. This is not stam a thank you to Hashem for all he has done, but it a statement by Yaakov of who he is. The crucial words uttered by Eisav when he meets his brother are וַיֹּ֥אמֶר עֵשָׂ֖ו יֶשׁ־לִ֣י רָ֑ב אָחִ֕י יְהִ֥י לְךָ֖ אֲשֶׁר־לָֽךְ. Rashi writes כאן הודה לו על הברכות. Perhaps derech derush one can suggest that the first half of Eisav's sentence is no less significant to making that admission than the second half. יֶשׁ־לִ֣י רָ֑ב remains Eisav's identity, and therefore וְרַ֖ב יַעֲבֹ֥ד צָעִֽיר will remain his lot.
All this brings me to a piece by R' Yaakov Abuchatzeira in Machsof HaLavan. Rashi and Ramban struggle to make sense of the word וַיֵּאָבֵ֥ק. This is the only context in Tanach where אבק appears as a verb. Why would the Torah use this strange form of the word and not some other, more common word, to desribe Yaakov's struggle? In Machsof HaLavan he points out that the word אבק has the same letters as the root of Yaakov's own name, עקב, with the exception of א in place of ע. The word עקב stands of anavah, kedusha, and bracha. The battle of the sar shel Eisav revolved around that one letter ע and the midah of anavah -- would Yaakov remain true to his humility, to who he was? The substitution of א represents the word אחיות. The sar shel Eisav accused Yaakov of violating the issur of marrying two sisters. What I think this means is that so long as Yaakov remained humble, the personality of Eisav could coexist within himself without causing damage and he could walk in the shoes of Eisav to take the bechora, the brachos, take Leah as his wife on top of Rachel. However, were he to allow that personality of Eisav to consume and transform him were he too lose sight of his own identity, were the two personalities incapable of coexisting, then he should have but one wife and not two. Hence, the sar she Eisav's argument. The conclusion of the story is that Yaakov is give the name Yisrael. Says R' Yaakov Abuchatzeira, this is roshei teivos: יעקב ראוי לישׂא שׁתי אחיות. Yaakov remained true to himself, true to the midah of anavah, and therefore was worthy of Rachel and Leah both.
Sometimes we must put on the garments of Eisav, but that is just a tool. Our core personality remains that of Yaakov, filled with bracha, kedusha, anavah.